S14E4: Dating a Workaholic

Dateable Podcast
March 15, 2022
Listen this episode on your favorite platform!
March 15, 2022

S14E4: Dating a Workaholic

With thin boundaries between work and life nowadays, we're diving into the line between career-oriented and work-obsessed as we chat with Caitlin about dating a workaholic.

Dating a Workaholic

From meeting IRL in your city to a solo trip on the other side of the world, we're discussing how you can meet romantic prospects in the wild as we chat with comedian Will Rocklin about how he met his now-wife while on a trip to the Dolomites. We discuss the vacation mentality you can bring to all your dating interactions, how to open a conversation with a stranger in a non-creepy way, and why solo travel is going to be so hot for singles in 2022.

TW: We discuss fertility / egg freezing in the intro of this episode briefly. Skip this section if this is triggering in any way.

Thank you to our partners for this episode:

BetterHelp: Get 10% off your first month of online therapy at with the code DATEABLE

Murad Skincare: You can find Murad’s line of skincare products at Sephora, Ulta and Find the digital magazine at and the podcast “Well Connected by Murad’ wherever you listen to podcasts!

ZocDoc: Download the app at and download the ZocDoc app for free to search for a top-rated doctor

Episode Transcript

S14E4: Dating a Workaholic

00:00:01 - 00:05:02

The Dateable podcast is an insider's look into modern dating that the Huffington post calls one of the top ten podcast about love and sex. On each episode, we'll talk to real daters about. From sex parties to sex droughts, date fails a diaper fetishes and first moves to first loves.  I'm your host Yue Xu, former dating coach turned dating sociologists. You also hear from my co host and producer Julie Krafchick as we explored this crazy dateable world.

Hey Friends, welcome to another episode of the dateable podcast where we dig into the ins and outs of modern dating but also the wise house and what's of people's behavior. We're on it. Yes, we have an episode that's coming soon of why the what needs to be the question not the why. So we'll leave it at that. Let you all be intrigued for a few weeks, but it's a good one. We always have good ones though. That's true. What else is new? I'm saying I have a favorite episode, you know, the usual. Every week. Well, this week's episode is completely relatable for so many people. It's about dating a workaholic or maybe you are an a workaholic dating because all of us are have been trying to make work and life and dating all work together the last few years, especially a lot of us working from home, which I've heard that makes you work even more 'cause there's no separation of home and work. So I found this episode, especially relevant. Yeah, someone actually asked me earlier has this always been a thing or do you think it's new for the pandemic? And I think dating someone that's a workaholic or being a workaholic has been around forever, but it's just showed up in different ways with the pandemic. We're going to go into it today with our guest Caitlin, who was dating a workaholic, and the industry that he worked in was supply chain, which I think different industries got hit differently in the pandemic, too, that there's a lot just going on in the world that is outside a relationships. And we also differentiate two of being invested in your career versus being a workaholic. And there are two very different things. And we also find out that your work culture bleeds into your personal life culture. And a lot of what we experience at work, if we don't leave it at work, it does show up in our personal lives, especially in dating. And the reason why I say that is because I'm at my parents house right now whenever I'm at my parents house, I get very nostalgic and I think about old memories, right? And I remember this guy I was dating in New York and I couldn't remember how we broke up or why we broke up 'cause he was wonderful and we had a great relationship. So I dug through my emails 'cause our final goodbyes were through email and it was shocking because I totally blocked this out. We broke up because he was working and going to school at the same time. So he could not make time for a relationship. And I, at the time, was trying to be an actress and a TV host. So my schedule was really erratic and I go on auditions during the day and I'd be at home waiting for him to be done with work. And the point of contention for us was that our schedules never matched up. I ended up blaming this on him not creating time for us and his side of the story was that he felt so much pressure from me because he couldn't keep up with my lifestyle because he was so busy with work and school that he felt like he could not live up to my expectations of what a good boyfriend would be. And it's really interesting our back and forth in the email, I blame him for a lot of it. He blames me back, and at the end it was like, it was a very defeated response for him that was basically like, I guess we can never be friends or be in contact because it seems like you're just so over this. But I couldn't believe it because in my mind my memory was we were in such a great relationship with so much fun. I totally forgot that we had misaligned schedules and also misaligned needs. We'll schedule and can be a bitch and that can really make or break. I think every relationship does an equality time. And you know, it's one of those things I think we all have those breaking points in those moments that we realize that career isn't everything and I'm speaking for someone that maybe identifies a little bit as a workaholic and there's been times that I've thrown myself into work and really made that the number one priority. And I think it's hard because it's easy to be like if they wanted to they would. Yeah. But I do think it's when you're hitting them also and I don't know if this relationship you had was more in your 20s or early on yeah and I think a lot of times a lot of us are using those formative years after college to really establish ourselves in our careers. Like I know for me I really wasn't dating until the late 20s because I was so career focused and from an early age I got drilled into my mind just make sure you can support yourself.

00:05:03 - 00:10:04

Everything else will come after that. So that was always a priority for me. And you know, that's what brings me to current day where I'm freezing my eggs because you know everything happened a little later than I think you think growing up and in today's world, especially with women really focused on career. There's a reason why these corporate companies are giving benefits like egg freezing and ways to keep you in the corporation longer and you know a big part of why someone asked me or Janice our moderator made a comment that she thought it was interesting that I was freezing my eggs. We're most of the time she's heard of it being when you're single. And I totally get when you're single because you just don't know what's going to happen, all that. But I think for me it was, it became more real that this was something I potentially want down the road because I could see it and I think currently it's like I am focused on my career. I am focused on different aspects that I want to grow in the next couple years. So having that extra time, which is what egg freezing affords you. That's why companies are shelling out thousands of dollars to do this. It makes sense. It's balancing it all, right? And so you're done with the process, right? Give us an update. I am done. I feel relieved. You know, it went really well. It actually was better than I expected in terms of results of what they originally told me, so it was really great. I woke up from the anesthesia and I was like, I need to fall back asleep so I can go into the operating room. And then I realized I was already done. So fast. It was real fast. It was ten to 15 minute procedure. I was there for two hours total. Yeah. More time to prep and then they give you time to rest. I honestly have the best nap of my life. It was fantastic. So, you know, all said and done, everyone is a different experience. It was very positive for me. Glad I did it. There's even a chance I might do it again for better odds because I think the reality that I'm thinking too is this is the plan B but the older you get and the more you focus on other parts of your life, it may become the plan a and that's the beauty of science that it can be a plan. It can be an option down the road if you have prioritized other stuff like career and other aspects of life. Yeah, isn't it interesting that we all we are really wanting these days is the option, right? It's not like even if we don't necessarily thought about us wanting it, we still want the option of wanting it. Yeah. Kate Kennedy, we did this full deep dive for anyone that missed it. It was last season, the decision to have kids or not. So if you're new in these updates a bit interesting, you can get a lot more in that episode, but one of the things that she talked about, this paradox that the older you get, the more financially secure you get, the more your career is thriving, the least likely it is to have children. And it's almost like the time that you're ready, you're not ready because you're building up these other areas that it almost is like the cards are stacked against. Yeah, my friend may has been trying to convince me to have kids. And she had her first kid at 40, her second kid around 42. And her recent text to me was, listen, you've probably afraid to be an older parent, but it's good because you have the means to do so. You have more self awareness, you're more confident in your career. You won't feel like you're stuck in a relationship and you won't feel like you're stuck in whatever stress that you're going through because you have the wherewithal to work through the challenges as opposed to when you're younger and I was like, that is a really good point. I mean, to me, I just feel like, oh, down the line, if I'm 60 years old, trying to chase down a 20 year old, will I keep up, but she also made the good point is like, we're also a generation so focus on our health that we are going to be healthier 60 year olds than our parents. So we are more armored with the health and the benefits to chase after our kids, you know, even when we're older. Yeah. I think for me, it's time, the amount of time I have in my life. I must feel like this podcast is our baby. I don't know how I would work a full-time job and do this podcast if I had a kid, right? It's almost like the time that I'm spending on this makes up for the fact that I don't have a child to care for. And I think for so long, I do still get a lot of satisfaction out of career. That means so much to my identity and we have another episode coming up where we figure out what sabotage your love life and I identified as the overachiever, which I now realize how it's hurting me. It's sort of ways. So that's going to be a good one too. But I think in all of life, that's been so much of my focus that it's hard to imagine shifting to this world where your job is to care for other people.

00:10:04 - 00:15:04

And you know, I just had two friends over a little bit ago and one of them brought her four month old. And the other one brought her dog and I was like, this is the life I don't have yet, you know? But there's so much beauty of that life too. And I think I'm just starting to see that. And it's taken me a while, and that's the part that's the paradox, right? The less time you have when you need to see it. I think the fascinating part about you and I, it's funny that we're aligned on this is that we didn't think about kids without a partner. Yeah. And we both met someone that we can picture kids with. I don't know what it feels like to just picture life with kids regardless of the partner, but I definitely feel a stronger connection to kids now that I'm with a partner I can see having kids with. Yeah, I mean, I know a lot of people that's an underlying struggle with dating too that maybe you and I haven't had as much experience with is this I know I want to have kids. I know I want to prioritize my career but the clock is ticking and I'm not meeting someone and that can be so stressful and again I think everyone needs to make their decision on the freezing your eggs, but there is I've heard people say it does alleviate some of that pressure to find someone right away when you know you want kids no matter what. You know, I heard something really interesting from my friend Ryan. I'm going to give him a shout out and you know him, Julie. So my friend Ryan just came back from over a year living in Taiwan and he said in Taiwan, if you get divorced and you have kids, the kids automatically go to the dad. Wow. Because they want women to have a higher chance of remarrying, and they know that their chances are lower if they are single mothers. So isn't that interesting they immediately default to the dad and the woman would have to fight really hard to get full custody or even partial custody. So this way society is saying this allows for women to remarry. Fascinating. That is fascinating. I mean, I think I'm also always fascinated at the stats of the gender pay gap is actually between men and women. It's not that much difference. But where it becomes different is women with children. That's when there is a huge pay gap in, you know, I think we just can't be naive to say that having kids doesn't affect your career. I think, you know, there's some people that can make it all work, but it's hard to do it all. Yeah, being on the receiving end of recruiting and hearing recruiters talk about, oh, woman being of a childbearing age, should we stay away, has been a real discussion. Yes. It's not legal, but I've definitely heard it. And then in China, it's completely legal to think that way. So in China, I think you get a year's off for a maternity leave. So a lot of companies would stay away from women in their late 20s and early 30s for that reason. That is wild. I feel like that is so illegal, but that is wild and you know I think people do have different perceptions of women that are single. There's this feeling like they have more time to be spending on work, which is unfair and different ways. I feel like when you have kids, pretty much anything you say that, oh, I need to attend to my kid or I need to do this. It's like great. Go for it. If you were ever to say I need time off to prep for a date, people would laugh at you. And they'd be like, hell no. There's no, there's no grace for single people at all. It's more just work, workload, continue. There's this myth that single people just want to keep working and they have all this free time to work all the time. That is such bullshit. And that is so related to this episode and that is so related to our question for this episode, someone wrote in and said, I'm seeing someone right now who keeps saying that they're busy with work. What should I do about this person? How about we all been there before? I know. I certainly have. You know, at the end of the day, their priority is not you. Whether that's an accurate statement that they are too busy with work or it's an excuse, I think sometimes we justify work as a way out of other things. It's an easy one to say, I don't have time because I'm working. It's almost like taking care of kids. It feels justified that people can understand that reasoning. It almost doesn't matter because at the end of the day they're not giving you what you want. I think you could have a conversation with them and say like, hey, I'm at a place in my life. I'm looking for a committed relationship where I spend quality time with my partner. I'm really excited about you and where this is going, but I feel like that part's missing. What can we do about it? And see how they react to it. That's the only thing you can do in this situation. People who pour their heart and soul into work are people who somewhat have an avoidant tendency towards relationships.

00:15:04 - 00:20:02

So we hear this from people who love to go to work because they have more control at work. They have more power at work and they don't feel that they have that in their relationships or they don't know how to communicate the needs that they need in a relationship to their partners so then they just, again, avoid it by getting work in the way and using that as an excuse. But like what Julie just said, anybody who pours so much of their time into work is not prioritizing you and it's at this point there's no need to even ask why are you doing that at work? It's proof is in the pudding action speaks louder than words and if you're seeing an imbalance of time spent between work and you, then you kind of know where you stand here. So I think in this situation it is important to have a heart to heart conversation with your partner and say, listen, I want to be a priority too, but if work right now is what you want to prioritize, I respect that. That's not what I'm looking for. And I think we should respectfully exit out of this relationship. I agree with most things. I'm not sure if I agree that it's always an avoid intendency. I think that can be won for sure, but I think some of it is, you know, if you I'm just thinking about like from the overachiever perspective, if you've historically haven't had good results in the dating world, but in career, you're always promoted. You're always told that you're really great at your job. You're gonna funnel more energy into that aspect of life because you could see the direct correlation. Also, depending on where you are financially, it might be that you have to work. Like that might not be a luxury to cut back on work or maybe you just have bad boundaries. Your people pleaser. You can't say no to people at work. So you can't make those lines of personal life and professional life. So I think there's many reasons why someone could be spending a lot of time at work in prioritizing work. So that's why I think having it as an open question and getting to the root of what is driving them is so important. And then you can know how to proceed because I think we can't assume that everyone that dives into work is just avoiding relationships either. There is something to be said about people who are in good relationships that it becomes a default. So then they don't feel like they have to work towards that relationship. So then they pour that energy into their work, right? So it's like, oh, I'm dating someone. I'm good. I don't need to think about that. Yeah. Category. I can just focus on my work now. And I hate to be on the receiving end of that because you're like, wait, if we created this good relationship, and now you're basically throwing it away. I mean, I felt myself start to think that way, but we were like three years resolutions. And I had to stop and be like, nope, this doesn't ever stop. It's not that you just got the partner now it's done and you can move on to another area of life. I really think if you want all these facets of life, you need to find the way that you can balance them. And that might mean that you don't give a 120% to work. Maybe you dial it down to 80% and you could still be killing it at your job and progressing your career that way. And sometimes more time doesn't always mean that you're actually giving better results either. Sometimes being smart and work is knowing what to focus on and what not to focus on. So I think it's getting really clear of what's important to you as the person may be working too much and then the person that's on the receiving end and seeing how you can learn to balance better if both of you want to go that route. Well, we have so much more info in this episode. All about this topic. You know, we go into it all. And you know, there's no wrong way or right way to do any of this. It's all what works for you, but I think with a big point of this episode is it's great to be career oriented, but not necessarily at the expense of everything else in your personal life. There is always a balance that needs to happen. Everything in moderation guys, everything in moderation. Yep, that's where the word aholic comes from, right? It's the same as alcoholic or any other type of aholic. It's the obsessive compulsiveness of it, not that you're doing it. Okay, so time for some announcements. We are so excited that we've been having the cameos role in lately. Just recorded one right before this and we love how creative you all are getting with the cameos. For people's birthdays, when your friend breaks up with someone, getting them pumped up for date or yourself, we've had a few that people have written in for their own first date pump up and then some for their friends that are getting back in the game. So there's been so many creative ways to use cameo and we've just loved recording these. And also, if you just want to like call out a ghost or call out someone who wronged you, we're so good at that.

00:20:03 - 00:25:01

You don't have to do it. We'll do it for you. We're here for it. We're here for it. We haven't done those yet, but we are here for it and ready to go be our first. Take our virginity on that one. So you can find us on cameo just by searching for a dateable podcast. We'll be the first one that pops up. Awesome. Okay, other announcements, loving the time of Corona as our Facebook group, the sounding board is our premium group, reminder to register at did will podcast dot com slash sounding board will let you into all the weekly sound offs, the office hours with the two of us, but you do need to go through that website to get in. So just a PSA gets we're not ignoring you. I want to say that every week, because I don't want all the people that are pending to think that we're ignoring that. But there is an extra step there. And then at dateable podcast is us on Instagram. And TikTok, we need to grow our following a TikTok. So help us out. We're fucking everywhere, okay? Okay, and let's do a few quick messages from our partners for this episode. This episode is sponsored by better help online therapy. Relationships take work, especially the most important one you have in your life, your relationship with yourself. A lot of us will drop anything to go help someone we care about. We'll go out of our way to treat other people well, but how often do we give ourselves the same treatment, so this month, better help online therapy wants to remind you that you matter just as much as everyone else does, and therapy is a great way to make sure you show up for yourself. For me, therapy has been an eye opening experience, because I didn't realize how much I needed the support and tools to process my feelings. Better help is online therapy that offers video, phone, and even live chat sessions with your therapist. So you don't have to see anyone on camera if you don't want to. It's much more affordable than in person therapy, and you can be matched with a therapist in under 48 hours. Give it a try and see why over 2 million people have used better help online therapy. This podcast is sponsored by better help and dateable listeners get 10% off their first month at better help dot com slash dateable. That's BET, TER, HELP dot com slash DAT ABL E this episode is made possible by zocdoc, finding and booking a Doctor Who's right for you doesn't need to be a terrible experience. Will they take your insurance, understand your needs or be available when you can see them with zocdoc, the answer can be a refreshingly pain free yes. Zocdoc is a free app that shows you doctors who are patient reviewed, take your insurance and are available when you need them. You simply just go to Zak Doc dot com, choose a time slot and whether you want to see the doctor in person or do a video visit and just like that, your booked, and that's exactly how I found my new doctor after moving to LA. Every month, millions of people use zocdoc, and I'm one of them. It's my go to whenever I need to find and book a doctor. Finding a quality doctor really shouldn't be that complicated. Zocdoc makes a search so much more pleasant. For our listeners, go to Zack Doc dot com slash dateable and download the zoc Doc app for free. Then start your search for a top rated doctor today. Many are available within 24 hours. That's dot com slash DAT ABL E Zak Doc dot com slash dateable. Okay, let's hear it from Caitlin about dating a workaholic. In this time of working from home especially, I feel like it's so easy for people to be workaholics and be busy, busy all the time. What's funny is people tend to use working and being busy as an excuse to not be fully present when they're dating. So I'm curious to hear your stories, Caitlin, who is she's 34 years old, she lives in Florida originally from Houston, Texas. Currently hooking up and having fun and dating someone but haven't defined the relationship. So all of the above when you have to check those. Welcome Caitlin. Hi, everyone. How y'all? Ah, there's a Texan coming up. I love this topic because I do agree with what you said you were. I think the lines of work and life are very much blurred with this new world that we're into, but also on one side you want to balance your career and balance relationships. So it's not always a bad thing. I was curious what the formal definition of a workaholic was. So I looked it up. So it is most researchers define a workaholic as a person who works excessively and compulsively and is unable to detach from work. And I think that's important because we all define working a lot very differently based on our own definitions of work. So yeah, I guess Caitlin. Maybe to start off, let's spill the tea. I want to hear a little more about the current situation you're in with the workaholic. Situation would be the best way to describe it.

00:25:02 - 00:30:08

I just listened to your episode about situation ships. I thought, oh yeah, this is me in this workaholic right now. So about a month ago, it was about the last week at my job. I am switching jobs, which is why I moved to Florida from California. And there was a very high up man at the location where I was at in my workplace, and I do not date coworkers at all, but I just had this vibe and I told myself, you know what? I'm gonna just plant a seed with him and if he fights back, you know, if he takes it great, if not great. So I went to my little small circle at work and I said, hey, you work with him. More than I do. You know, please keep this to yourself. I'm thinking about reaching out to him, romantically. I've never done this before, but let me know if he is he the work fuckboy or, you know. And they said, go for it. He's wonderful. Go for it. I said, perfect 'cause that was my instincts because what I was really attracted to was his leadership style, the way he worked with his team and the numbers that he has done at work. And it's really phenomenal. So I reached out to him about a week before my last day. Again, I don't date coworkers, but I figured a week before would be fine before I left. And I said to him, you know, I really liked your leadership style and enjoyed working with you and I want to help you be successful when I leave. I'd love to get a drink with you to talk about my experience with you and he was completely down with it. Well, all of a sudden it turned into more work and then we got very intimate very fast, very close. And it got very romantic about a week or so later. So romantic that he booked a weekend in Seattle for us a week after we connected. So wait, I feel like there's a mystic piece how did it go from? We want to talk about work to intimate, that you're booking trips to Seattle. Well, we started drinks to that take. I'm just that good y'all. I'm just that good. True. No, he just we were just talking on text and phone calls. It just turned into this, you know, which is a natural conversation. We really just connected in our communications. And we went on a date, the Sunday before. I mean, we just weren't really fast. And we went on our first date, the week before, and just really connected. He stayed with me two days later when I went to San Diego to see my friend on my farewell tour for work. And then that weekend, we were in Seattle, moved very, very fast. Wait, I feel like this story is juicier than the workaholic bit right now. Okay, so I feel like I want more detail work on we want to go here. We'll get there first, but I think the starter of this relationship is probably what's most fascinating for a lot of people listening right now. So I just want to ask a few more questions about this stage. Okay, so when you reach out to him, this is purely for work purposes. When was the turning point? The tipping point, I guess, when you both felt safe to talk about your relationship in a romantic sense. I started talking to him about my experience of in California because he said, you know, was it California? Or is it the job while you're leaving? I said a little bit of both. And then he's been single for about four years. About four years ago, he went through a divorce, yes. So we had that connection because there's not a lot of single men at my work. Or my previous job. And we started talking, and I said, you know, I know you're single too. How was dating been for you? And, you know, he said a little bit, not that much dating either. Like, I have it today that much. So I opened up with him and I said, this is my experience with dating, and then he told me his experience. So I felt me personally, I felt heard when he was listening to me about my work situation, what I was sharing with him, which led me to open up and like, how can I go a little bit deeper 'cause I have a little warm and fuzzies with him. Which is interesting because the pandemic not dating can mean so many different reasons. It could be that you're a workaholic. It could be that you're concerned about your safety. It could be so many different varieties. So I guess at what point did you realize that you felt like the sky was a workaholic? Oh gosh, they were about to get real intimate Ariel. So just get ready. I know, I know. So when he was with me in San Diego, that was the first time we were super intimate. Like, you know, what couples do in the bedroom all the way. And thanks. And spelling it out for us. What couples do really intimate have sex? So, oh gosh. So we were, it was about 6 a.m. the next morning, and he was reading his emails. And to give context to him and maybe we can elaborate it later, is he's a very high up in supply chain. And unless you're living under a rock or having to the grocery stores lately, supply chain is a very, very difficult industry, very difficult. And it's a 24 hour job, so I kind of give him grace for that, but we were he was checking emails and then we started being intimate, having sex, and then he left in the middle of it, and he said, I got to be there for my team. In the middle. In the middle, like he just pulled out of me and wait, was there a B day that he was going to or was it more just a hypothetical idea by brain is on work right this minute? Our brain is on work at this minute.

00:30:09 - 00:35:01

Oh my God, it's so whisky dick. He had work dick. And I'm like, what does this have to do with numbers or performance or your team right now? Like your intimate with me. What? Right. That's running through your head right this minute, as we're doing this. Yeah. So I text very close friends after he left. I said, my name is Caitlin. I think I'm dating a workaholic. And then to this continue. It's like dating him wise or just the behavior, the workaholic tendencies. Well, we went to Seattle that weekend because he told me before he left after that moment. He said, I'll be more available more present this weekend. I promise. I said, okay, maybe out of sight out of mind, different state, maybe he'll be more present. It did not show up intimately, but when we were out in Seattle that weekend, he was checking emails, he was still talking to people. He was talking to me about work. I want to say at least combine together between the two days. We were there at least 6 hours of the time. So these were both on weekends when it was unable to detach from work. We're not even talking about like midday being able to think of it. Well, the San Diego incident where we hooked up, that was a Wednesday morning. Okay. So that's why he said, you know, I'll be more present this weekend when we're in Seattle. I said, okay. He was still checking emails and working for about 6 hours that weekend. Wow, Julie, I'm rereading your definition of what alcoholic workaholic keeps me alcoholic. Who is someone who works excessively yup, we saw that come through compulsively, yeah, pulling out of you in the Middlesex pretty damn compulsive and unable to detach from work. Like he hit all three to a T from just that one weekend. Yeah, and you know, I try to give him grace too because again, he's very high up in supply chain and it's a very, very hard industry right now. And I feel like there's workaholics pre COVID and like y'all mentioned, you know, when COVID, it's very easily to be a workaholic. If I look at our leaders, VP, senior vice president, CEOs, if any company, it's like a different level of empathy and compassion that you have to have as a leader because people are burnt out. People are frustrated. They're exhausted. So there might be some sort of guilt or, you know, if you step away from however many people you manage, you might feel like I'm letting them down because they're so frustrated and I feel like I have to be their present at all times to keep them motivated. So it's like a different kind of workaholic. That's a really good point because we're in the great resignation also. So I think some of it's probably the empathy base that you just brought up, but also probably the fear of losing people too and just creating more work to rehire and all that. Oh, absolutely. That was a big concern when I put in my resignation. They said, wow, you're a high performer. We need to talk. So why are you leaving? They were very, very concerned. Which is a good segue because you are someone that's career oriented yourself, right? It's not like you're just like, I don't care about my career. I just want a date. That's the only thing that's supported to me. Because we know you, we know that's not the case. So I guess how do you find balance in your dating life to separate career in personal life a bit more? You know, just to back it up a little about 5 years ago, my last long-term relationship ended. And for about a year and a half after that, I first discovered the dating apps. I was super hardcore into my work. I dated someone for about three months in a turbo relationship, which ended up being me being dosed around that time all my Friends were dating, getting married. Having the kids and I just was bottling up all my emotions and finally it just broke one day when I walked into work, I just cracked bread and emailed my company is merging with an industry giant. I just broke down. I thought, wow, the one thing I had going for me is probably going to be taken away. So I realized at that point, you know, once you put yourself all into work, you're really missing out on things in life because you're just a number. You could be asked immediately or a pandemic can wipe your industry away. So for me, I realized if I want to be a better teammate professionally, if I want to be a better partner, a better sister, a better friend, I need to have that balance because when I'm rejuvenated when I exit, I'm more present in just a better person overall. So that moment that whole year and a half where I just bottled up my emotions and then I cracked when my work was potentially taken away from me when I realized, you know what? Gotta balance. Yeah, that's a really good point because how you treat work actually bleeds into your personal life and vice versa. And just from my own experience, some of my worst managers have been the ones who've been bitterly single and not dating and refusing to connect with humans and they're at work till 10 p.m. and they expect you to be at work until 10 p.m. as well. And it doesn't do much for team morale that way.

00:35:02 - 00:40:05

Yeah. I mean, I definitely consider myself a career oriented person too, but I think there's this saying that on your deathbed, you're never asking if you could have worked more hours. You want to have more hours to spend with your loved ones. And especially at corporate America, you said this Caitlyn, you can get replaced in a second. If something, if something was to happen to you, there would be a job description up within hours to try to backfill you. Where your personal life, you can't backfill someone that way, because there's so much more that goes into it. So I think there is work is important. It's not like it's not important. It gives us purpose. It also helps us financially pay for things. But then they're also needs to be the line of, this isn't my whole world either. And I wish I had that with the workaholic situationship I'm in because he talked to me about his divorce from four years ago and people go into work. I feel like people put their effort into work too to cover their emotions. They might be feeling just judging on the actions I've seen with him. I don't think he has separated those two yet. I think a lot of people do that. I've been there before when going through a breakup. It's easier to suppress emotion. It just funnel all your energy into work. Absolutely. Yeah, and when you're succeeding at work, when you're putting your work into it, you're succeeding, you're kind of addictive, you know? You just fall into that trail. Well, it makes you feel like you have something under control. If you don't have your personal life under control, at least at work, you feel valued. So now that you're in this situation and you have a known him for that long in a romantic sense, have you been able to call him out on some of this behavior? You know, after Seattle, I felt him get a little distant, and my gut was talking, and I thought, you know, it's my first week at the new job, maybe he's giving me distance, work is work his work. But then finally, I said, I need to speak to him, so I said to him, look, my gut is talking right now, our vibe is off. Again, my gut is talking, and I'm just reaching out to you to see how you're feeling. And he said, well, I'm not planning on leaving California for a few years. You're going to Florida. How can this really work? And you said, you're considering Florida being your forever home, what does this mean? And I said, okay, I see where you're going with this. You're a great memory of California. I glad you were part of my short time here. And he said, no, I still want to be friends. You know, I'll come see you in Florida and I'll come travel. But he hasn't planned anything. He hasn't really been vocal about seeing me ever since then. So I'm not quite sure if his words and actions were lining up right now. Interesting. It's kind of just now faded a bit, but was there anything you said when some of the behavior was coming in around work life balance or do you have any discussions with him? I mean, I made comments to him like, hey, like stop. Stop and he just, I don't think he could stop. I didn't really have to long conversations. It was just very light. And how did you react when he pulled his penis out of you? Romp to think about work. I was speechless. I started questioning, was it me? Is it me? Did I do something wrong? But then when he said, I'll be fully present this weekend. I clicked, it clicked at that point that it wasn't me. It was it was him. I feel like we kind of skipped over Julie, because I feel like you've dated workaholics before. Love to hear your experience of what you had to deal with. Yes, I definitely dated a work on. Maybe there was one person that particularly stood out. And I think one thing that I dealt with was it was always on their terms at first, I thought it was really awesome that this person was making all the plans and deciding what restaurants to go to and booking the reservations. I was like, finally, someone super proactive. But I quickly realized that any time I suggested something, it was not met because it was all around his work schedule. And that was what was driving the proactiveness. So I think that was one piece that was challenging with it. I think the other was that it plants would get broken during, you know, there were times that we had plans and it was like, oh, I have to work late. And it didn't really feel like there was a remorse from it. And I mean, I don't know what their work schedule was really like. Maybe it was so urgent that they couldn't do the plans of me, but I had trouble seeing that. So I guess what I would have hoped for is one, is that really actually the truth. Could you do it tomorrow? It's still make that room for someone or was this just you saying you didn't want to make for someone? But then also if it truly was like, I need to do this tonight, having more visibility into that.

00:40:05 - 00:45:02

And I think that's where it goes back to the communication aspect of just getting like, oh, sorry, I got to work late. That doesn't do it unless you're really sharing what's going on for you. Yeah, I guess you have you ever dated a workaholic. I've never dated a workaholic in the traditional sense, but from this discussion, I realized I've dated someone who was married to their work and I was their mistress. And that didn't make me feel good. It didn't mean that he was working all the time, but he certainly talked about his work in a much better light that he was talking about me. And he would often, during our short lived relationship, he would often text me articles like tech crunch articles about his industry and his company, yet his coworkers knew nothing about me except for my name. But I knew everything about his coworkers. So that was a huge red flag. He was married to the sexy company, and I was just there for a distraction. And even after we broke up, he was still semi articles about his company, the IPO, and oh my God, look at how we're doing. I'm like, I don't give a fuck. You know what? It'll work there. What are you saying to me this? I have the same thing happen with the workaholic. I just mentioned, is that once we called it, he would send me articles all the time. He didn't send him about his company, but he would send them about. I was working at Yahoo at the time. So he would send them about the tech industry. And it would almost be like his way to get back in touch, but it would just be like him sending a tech crunch article after speaking for weeks. And it was like, what does this mean? And of course, I would start to wonder if this was a sign that things were back on because I was clearly not as enlightened as I am now. This was many, many years ago. But I think that was a big thing that a lot of our communication was done through his work email the true super weird. What? Looking back on it. He wouldn't even text all the time. It would just be sent from his work email. And I'm like, why would you even want these and some of them were a little racy? I'm like, why would you want this in a paper trail from your work email? But I think it's like he couldn't even detach that much to go to personal email. Wow. Wow. I think this stuff directly affects me, but a sign was the he also had told me that he was supposed to go home for the holidays one year and actively chose not to. So he could work. So I think that's actually a good way to understand someone's relationship with work too. It might not be how they show up for you, but how do they show up for other people in their lives? If you're dating someone successful, but they balance friends and family well, but that could be a sign that they have better balance than someone that has no friends, doesn't ever see their family. That's a big piece of it. That's a good point because I turned in my notice for my job in Florida right before the holidays. And my mom said, are you sure you want to come home? Do you want to start packing, you know, get moving. And I said, nope, I want to see my family because might not ever see all ever again. So I'm not going to turn this down. I will be there for the holidays. That's huge. I think that's such an important question to ask in early dating is who are the closest people in your life and how do you show up for them? And I can guarantee you that guy dated would have named 5 of his coworkers, including his boss. It's like my best friend is my boss. Angel investors by BFF. Yeah, exactly. That's exactly what it was. We went to a wedding of one of the angel investors of this company. Do you know anything about him or you just know he has money? Let's hold that thought for a few quick messages. This episode is brought to you by murad skin care, a line of clinically proven cruelty free products that meet the meticulous standards for safety, efficacy and care you expect from a doctor. One of my favorite products is the invisa scar resurfacing treatment, which I've already seen some results from from using it for just a few weeks. Founded by doctor Howard murad, who is a board certified dermatologist and trained pharmacist, recognized around the world as a visionary for his unmatched scientific innovations, murad has also launched a digital magazine and a podcast called well connected by murad, connecting the dots between science and wellness, find the digital magazine at well connected dot murad dot com and the podcast well connected by murad wherever you listen to your podcast and for data listeners only go to Mira dot com and enter the code dateable for 20% off and free shipping for orders of $60 or more. Again, that's murat dot com and enter the code data date for 20% off and free shipping for $60 or more. This episode is brought to you by drizzly. If you look for it every day has cause for celebration. Celebrate a friend for their promotion, baby, wedding life thing.

00:45:03 - 00:50:05

Celebrate yourself for keeping the couch warm. It's no easy feat, especially if it's a big couch. Or maybe you just want to celebrate living in 2022, where you can get beer, wine, and spirits deliver from drizzly in under 60 minutes without leaving, said couch. No wonder drizzly is the number one app for alcohol delivery. And remember to share the love, you can get alcohol delivered to your friends and your coworkers, what a nice surprise. Right now, drizzly is giving all new customers $5 off their first order with the code fast 5. So download the drizzly app or go to drizzly dot com that spelled DRI Z, LY dot com and use the promo code fast 5 that spelled FAST number 5 for $5 off your first order. You're welcome. Have you ever thought about how much better dating would be if you had a whole army of people supporting you along the way? We know that dating can be frustrating and lonely, but it can also feel fulfilling and fun. Have you recently decided you want to make some changes to your love life? Maybe you've recently reentered the dating scene. Maybe you've gone on one too many dates that went nowhere, or maybe you're just ready to take your current relationship to the next level. That is exactly why we created the sounding board, a true extension of our podcast that delivers a personalized experience, which includes monthly office hours where you can drop in and chat with us about anything. Weekly sound offs with guided discussions and regular virtual happy hours, allow Julie and I to become your dating sherpas to provide real-time guidance and wisdom in a more intimate way so we can all navigate dating and relationships together. Join the sounding board today by going to dateable podcast dot com slash sounding board. Again, that's dateable podcast dot com slash sounding board and you also have dated people across the spectrum in terms of occupation. And I just know you because you are one of our moderators in our Facebook group that you have shared an experience that a long-term relationship and did because the person wasn't career oriented enough in motivated enough, basically the opposite side of the spectrum. I guess what is kind of for anyone that doesn't know you. What is kind of your background with people in occupations and how has there been pros and cons of both? Oh gosh, where to begin? I've feel like I've dated them all. I mean, I watched Sex and the City in college and for some reason I felt like I just had to translate my dating in that. So I have dated bartenders. I have dated VPs and tech. A VP of tech, entrepreneurs, gosh, I've dated them all. I feel like. And there are pros and cons to both. So my last long-term relationship that ended 5 years ago, he was hourly at Home Depot. I mean, very complacent, not super career driven, but he was the sweetest and most loyal man I ever dated. And he let me be free. He didn't care what I did. He trusted me, but he was also just complacent about everything, whereas before him I previous long-term relationship before him was a military officer, which was completely different of completely different personality. He was very regimented and I like routine, but I also don't like being told what to do all the time. So that was one career that did not work out for me. I've also dated PVP very high in tech and we connected on so many things emotionally, but it was a turbo relationship with which ended up with me being ghosted after three months of traveling all over the country. So, you know, they all have different stories and I've noticed the higher up men are, just from my experience, I don't want to generalize, but the higher up men are, the more they're so successful in the boardroom, they can do anything and lead teams at 300 hundreds, but in their personal life. Again, I'm generalizing just from my experience. They're not all emotionally there. Like they're just not their emotional intelligences very far and few to find. Whereas the hourly from Home Depot, he knew me very well. He picked up on the little details. He was there for me. He knew what my love language is where without me telling him. So I mean, there's pros and cons, you know, do we want the motivated, emotionally unavailable, driven man, or do we go with the complacent loyal suite hourly worker? Right. And it doesn't always have to be one or the other. I know you're generalizing just on experience. But I think you do raise a good point that just because you have the skills necessary to lead a business. Does it mean that you have the skills necessarily to lead a relationship? And I think a lot of times we struggle with relational skills because our generation, particularly, has put career first a lot of times. And that results in getting into relationships later in life and maybe not even knowing how to really navigate them. Yeah, that was interesting because I dated a man very high up in Silicon Valley and one thing I'll never forget.

00:50:05 - 00:55:04

One thing he said to me was I am so jealous that you can be alone and be okay with it. Like you can go home to an empty place and you're fine, whereas I have to have someone I have to do it. I have to just be around someone at all times to come home to. And I think to myself, you have changed the world with what you've done, but you can't go home and sit alone. I mean, that was really mind-blowing to me because just because there are certain way in the boardroom doesn't mean they're that confident when they go home. Yeah, and I think that's the conflict that we see too is a lot of men that we've spoken to have often said, I have to get my career in place before I can focus on my personal life, but for many people, once they think they've reached that point in their career where they have it made or they've succeeded, then they have a lot of catching up to do when it comes to their personal life because it's been years since they had to have a very real relationship and a friend of mine comes to mind. He just recently sold this startup. He was in a complacent relationship, didn't work on it in the moment he sold his startup. He broke up with a 15 year whatever that was and said, I need an actual relationship now. Where do I start? How do I begin? So how do we, I mean, we're going to see more and more of this. And I'm saying this for men only because the men have spoken out, but I'm sure it happens with women as well. As we see more and more of this in our generation, how do we, I guess, let's go from the person dating the person who's a workaholic. How do we support them, but also draw boundaries at the same time? I started not initiating first in the morning. I found myself initiating, I thought, you know what? I'm going to set the boundaries set. Isn't this is not going to be a one way street. It's going to be a two way. I haven't heard from him in two days since I haven't initiated. So just change it up your actions, I feel like for communications that that boundary. Yeah, I think we've heard this before from experts to that have said this, that there's getting out of work mode before you go on date mode and maybe that's just decompressing in a way that you can have that delineation a bit more. And if you're dating someone that has workaholic tendencies, encouraging them to kind of finish up what they need to finish up, even if that means you meet up a half an hour later. But just so it can be done. And then you can move into the date mode. And I say this sort of somewhat that is probably the workaholic in my relationship. And I've dealt with this. So I guess that's an example of women. I think it reads both ways. I don't think this is a male exclusive thing at all. So that's a really good point. I have my own personal rules when I date. I only date on the weekends, like first dates until I get comfortable with you. I will not date Monday through Friday because I'm not fully present because I don't know how much how hard I work. I'm not going to show up and just talk to your ear off about work at happy hour. But I want to get to know you and be in the right mindset. So that's my personal role with dating. And I actually brought this up with one date about two years ago. You wanted to see me more. He said, I want to see you more. I want to see you more. I said, I don't know you well enough to see you on a Tuesday yet. I won't, please. You will get a better date with me if we meet on Saturday or Sunday. And he really didn't like that. And we didn't work out. I like that. 'cause you know yourself so well that you can communicate when you are in the best mindset. If you're dating someone who is a workaholic, you also challenge them to think that way too. I want you and all of you. So give me the days and times that you think you can be fully present where I don't want to see you because it doesn't do any of us any good. That's a good point. If workaholic reaches out to me, I can say that to him. I think that's important. And I think not having your phone out when you're on the date is really important too, because we're so glued to our phones in this day and age. If he, I'm guessing, probably saw out of the corner of his eye, something an email go through or a calendar invite. If you see that, it's hard not to respond to it. So I think just putting it in your bag or in your coat pocket or something away when you're in date mode time is super important because then you don't even have that temptation. Absolutely. He probably was checking emails when I go to the restroom. Walk away for a second. I think I used to have a rule two of just not talking about work. I didn't like to talk about work on dates. It wasn't like a rule I just really communicated, but for me, I wouldn't, I wouldn't hide anything if someone brought asked me what I did for work. I would obviously tell them. But I would try to move the conversation along. It does something a little more fun and upbeat, especially for the first date because it's important to understand someone and where they're coming from and what drives them.

00:55:04 - 01:00:02

But I think you could do that later on. What I wouldn't want to get sucked into is the mundane aspects of work because let's be honest, if you're not in someone's industry, you don't want to hear about that anyways. And even if you are, when you're out for drinks, it's questionable if you want to hear about it. Yeah, that's not exciting at all. And there's something very fascinating that happens because we had an episode about dating the CEO of a startup. And the entire 60 minutes the sky is talking about how he's not ready today. He doesn't have to the time to date. He's married to his work and his staff are his kids, and we receive like 50 emails after this episode aired of women who said, I'm okay with that lifestyle, or I'm ready to change your lifestyle. And I think we just have to be on these first early dates, just take it at face value. This is what this person is saying. If they say they're not ready to date, they don't have time to date. They really do mean it. And if you think you can be okay with that lifestyle, I think it's better to really be honest with yourself and ask, am I really okay with this lifestyle? I used to be that person who thought, oh yeah, I could totally date an executive who has, you know, maybe sees me once every other week and it's fine because they're high up and the time I get to spend with them it's fine. I've also realized I'm not that person anymore. I can't deal with that because that's not a relationship in my eyes. Yeah. I mean, I think the other piece, like I bet I would try not to talk about work on deets, but I don't think that that means that you can't hear how they view work. And I loved always asking people the question too. If you won the lottery or something that basically made you never have to work again, what would you do to hear kind of like what they like, how their mind operated around work or also just asking them, what was important in your life, like from accomplishment perspective, just understand their why behind working too, because I think that's something that we haven't hit on yet, is that work does mean different things for different people. And some people are workaholics by choice because they've got extra time or they're just wired that way. But other people might be workaholics out of necessity based on financial means or if they're supporting children, there could be other reasons behind it. So I think understanding someone's why of why they work so much is really important. I love this. This speaks to me because I used to go on dates and they say, oh, what do you do? And I say I'm a marketing manager and a food industry, where I would switch it and say, I would lead more with I help restaurants survive. I help restaurants do their thing. I help restaurants stay creative, where it leads more to my passion of keeping the arts in school, how passionate I am for artists to make it and creativity and people connection, which leads more into that rather than my day to today work. So it's really how you market it on the date because the CEO of a tech story I could say I'm the CEO of tech startup where they can say I'm providing tech solutions to certain markets to help them survive. That's a great point. I think we are so tied to our titles that we're not tied to the purpose of the title. So maybe a better question on a date rather than what do you do is what's your purpose at work? What are you accomplishing there? That's a lot more telling than I'm a senior customer success manager. Good for you. I'm level three. Customers success manager. Super, I would definitely date that person. You have to that person. You had me at customer success level three, not two. Yeah. I'm not in tech, I don't mean shit to me. I don't know if that means. What if it's a power couple that both people are super career oriented, career comes above everything else? Could that work or is it doomed to just be a surface level relationship? What's that term we talked about once go dual income, no kids? Yeah. Yep. The dink couple. I don't know. I've never seen a dink. I don't think so. I know this couple. I know this couple. I've seen it, both of them are very savvy in their careers. They're very high up. And they spend all their quality time trying to brainstorm ways to accomplish even more in their professional careers. And then over a decade goes by and they realize they are just business partners and there's nothing romantic that is happening. And that's when you have infidelity. That's when you start moving to different cities and saying, we can make it work. It's for our careers, but we can make this work. I personally just don't see that happening.

01:00:02 - 01:05:02

If two people can not prioritize their relationship, then that relationship is definitely doomed. Well, remember we had Amanda Bradford on years ago. I think it was season two and she's the CEO of the league and we asked her if she would date another CEO. It's her response was neither one of us would plan anything. Right? So we basically both pizza busy. Nothing would ever get off the ground. It's kind of like to avoid people dating. Just nothing ever happens. And of course, there's always exceptions to the rule, but I think maybe power couples that have that can carve out that together time and have that balance have more of a fighting chance than if you're always on work mode. Yeah. Well, one thing I noticed with the workaholic, this was very interesting to me. I moved to California right before the pandemic and I had not a lot of intimacy or dating for about two years I was here. Physical touch was pretty much nonexistent while I was here. But I noticed with him one way I really got him to open up and just I could feel his body change was simple, physical touch. I would touch his back, I would link arms with him. Things I normally don't do, but because I've had such lacking a physical touch, I just felt just geared toward the simple small things. I mean, we were that couple on the airplane where I'm holding up to his arm, I'm snuggled up to him and I loved it and I could he received it so well. So I thought, okay, this is how he responds. He's a completely different person. I could feel a change in him on that. And I think if you're a power couple and you don't have that connection, you're not going to work, you know, like you saw UA, but I just picked up on that intimacy of fiscal touch and how important that is in a relationship with him. I will say the flip side though, because I do know some people that are very work oriented. But I do think they're able to turn it on and off. But I think the benefits of people that are CEOs or startup founders or something that really takes a lot of diligence is that they're very committed. And they'll do what it takes to make things work at all costs. And I think that actually can be an important trait in a partnership because you do want someone that, you know, once they're in and wants to like, this is what I'm doing. I'm doing it. I don't know. Some of the people I'm thinking of also are endurance athletes and I think it has similar characteristics to that too, right? Just like a drive to keep going with something. And I think there can be a flip side that is beneficial in relationships as long as you can find some of the balance. Then I would argue those people are prioritizing their relationship. That's what the commitment is about, right? So it's not about being career oriented. It's about making time for a relationship also. Absolutely. I mean, I was going to say that I think our society likes to romanticize busyness. Everyone's busy. Oh, goodness. I'm so busy all the time. And we hear daters making excuses for the people they're seeing, saying, oh, I haven't seen this person while they're so busy. They're really high up at work, or they're going through school right now. They're getting an MBA. We got to stop making excuses for busyness because nobody's that busy. The busyness comes from what people create for themselves, but there are plenty of hours in a day to not be busy. And if someone says they're too busy, that's a red flag. Let's talk about where this business is coming from. What are you hiding from? Right. Well, people want to make time for what they want to be time for at the end of the day. And I think if they truly are so busy with work, then that means that that's their priority. And it's not a relationship. And ultimately, it doesn't matter what they're hiding from if they're not ready to be in a relationship with you. It's not your role to be like Nancy Drew and investigate and figure out what is going on with them. You know, I was thinking, you know, before this interview, you know, how do you break? How does it workaholic stop becoming one? You know, how do we do it? And I don't think it comes from me or anyone else. It comes from within. I feel like they have to maybe hit a point like I did crack and think, you know what? I'm losing I'm missing the real point of life right now. Yeah, I want to bring that to this conversation then because okay, so we talked about there is a difference between being career oriented and being a workaholic. And the line really is making room for other relationships versus not. How do we then manage career with dating or in relationships? We gave a few tips of separating time. But that's not always realistic, especially if the relationship progresses. I know Caitlyn, you mentioned, you would only do things on the weekends until you got comfortable. But eventually you're going to get comfortable. And you're going to want this person there. How do we think that we can balance career in relationships? Magic. Create more hours. I mean, isn't that the $1 million question? Because we're all maximizers. So everyone wants to maximize their professional life as well as their personal life.

01:05:02 - 01:10:09

Think ultimately what I've seen with some of my work friends is they crack when it comes time for a celebration. Celebrating an accomplishment. They sell their startup with milestone birthday and nobody's there to celebrate with them. That loneliness really sets in, right? So you accomplish all of this, but you have nobody to share it with. So I feel like the answer to your question, Julie, is about constant sharing of a life with someone and knowing that when you go on these states, even if you're not completely intimate yet, sharing more of your life with them and allowing them inside of who you are, I think will create more of that less of that loneliness down the line. And I find that with a lot of workaholic tendencies, people close off and they don't want you to get too close because they don't want you to see their weaknesses, but sometimes being vulnerable is exactly what will help you to become more successful when it comes to your personal and professional life. That speaks to my soul so much you wear. I would love to celebrate my accomplishments with someone and I just haven't found them yet. And I was just I'm dying for that. And that's one thing I really liked about the workaholic is I felt heard when I talked to him about work. I felt, I mean, he's a great listener and which is why he's a really good leader at his job. He's a great listener. Very compassionate and just really made me feel like I could be myself with him. Yeah, no, I think that we all do want that person we can celebrate with. So I definitely could see that. I think you said something that actually reminded me of something that happened recently for B two. It's like this, how can you set the expectations and how can you have this? I think what I learned with my partner is sometimes I'll do work when we're watching TV for instance. And to me it feels like downtime, but to him it feels more like we're doing this activity and now I'm not present. So how can you say like, okay, we basically have the same expectation that this hour of TV is us doing an activity together versus saying, okay, this actually is us just having downtime. And I can do my thing. If you could do your thing. And ultimately, that is a piece of it is communication, right? I think the fact it always comes back to communication. But I think a big piece of it is that because you are saying that some of the times that you felt slighted was when all of a sudden this person would start doing things like in your me time or the time that you both had together. So even just saying I need an hour today to kind of like take care of these things. So I can put away my phone or we could be super present together. That could go a long way. I really like that. Especially if your love language is quality time, that's so great. I think every everybody should try to exercise that because especially with working from home, what I found with my partners, I don't know when they're working or not. 'cause it's all the same. So one thing we started doing is that we change outfits when we're done working. Well, like literally changing into our fun outfit, if I'm wearing my orange sweatsuit, it's like, oh yeah, okay, you weighs off work now. She's ready to party, you know? But I think that's what you need. You know, back when we were in the office, you come home from work, it's like, okay, you're physically home, that means you're off work. But damn, working from home makes it really tricky. Definitely. So I guess like what tiffs we have for anyone navigating this. If you were to go through this again, well, I guess you're kind of still in it, but if you were to navigate this differently, would you have a dress the situations in a different way at all? Absolutely. And I would have said to him, you know, this is where I am in my relationships. That's what I'm looking for. The story I'm at in my career and if you're available in present and maybe just share my background too with people and his type of role as well and just see are you going to be available and present because find the higher up you are. It's harder to be more available. Just really having those more vulnerable open conversations instead of because I felt like being him were talking a lot about work because we used to work at the same place, but maybe taking it a little bit deeper once we got to the more intimate conversations. I could see that especially with a coworker being hard to get out of that boundary of work talk. It's almost like we need to set a boundary that we're not going to have any work talk at all at dinner or something. And that's where I told him to actually set that to him. Maybe we were in San Diego or Seattle. I said, I hope we can stop talking about where we work at eventually as we evolve. And he said, yes, I would like that too. Never really happened. Yeah, that's tough. You have so much work tea to talk about. It feels so good and it's comfortable and it also creates a little bit of intimacy when you have that bonding topic. Well, this has been such a great conversation. I mean, I think there's so many takeaways, but I think the biggest one that's standing out to me is that having a balance between work and life doesn't mean that you have to have to dim your light at all.

01:10:10 - 01:15:06

It doesn't mean that you have to be ashamed of your work or put that as the back burner. I think you can be loud and proud about work. But it doesn't mean that it needs to be the only thing going on for you. And if it is the only thing going on for you, how can you bring more into your life or more people into your life to have that balance? Because I do think that said this at the end of the day, the most deported thing is the people in your life and accomplishments are great because they give you a sense of purpose. That isn't going to be what you're thinking about on your deathbed. You're going to be thinking about the people and where you're wired for human connection and missing out on that aspect of life. That is a shame in a way. So I think I hope that people, if you're either dating a workaholic or you identify with workaholic tendencies yourself, it can be an opportunity to not say that someone could never do it. He works stuff again, but more of an opportunity to see how can we bridge this gap to have more of a balance fulfilling life. I really like that. My major takeaway is we lack role models in work life balance, especially in Silicon Valley where we will suck Jeff Bezos dick and Elon Musk because, oh my goodness, there are the people to look up to in terms of what success is. But we have to question, is that what success looks like? To make more money than God and to not have successful, healthy relationships, and look at Mark Zuckerberg, who has been married to the same woman forever, but he's considered boring because there's no drama that comes out of his life. Isn't that just a better place to be? So we just have to look to ourselves and think, what is a role model that I should be looking after? And I think the separation of work and personal life. And like you said, Julie, it doesn't have to be that you have to hide what you do, but I think we can always find ways to enhance one place and the other. So your personal life can always enhance your professional life and vice versa. And the right partner will help enhance both scenarios versus taking away or making you sacrifice, that should not be what a healthy relationship is about. And I hope we can just rewire the way we think about work and life and it's not a completely separate entity there. And finally, I think a great question to ask on first or second dates is how do you like to date? What is your dating style? I think the cis says so much about if someone's squeezing in dates in between meetings or weekdays or you get someone like Caitlin who says I date intentionally only on weekends because I want to be fully present. That just says so much about someone's relationship to their time in general. So those are my key takeaways. Caitlyn, any words of advice for our listeners who may be either the workaholic or dating a workaholic. I think it's important to know who you are and what you will and will not put up with. Or you will will not stand for having those core values. And you'll know when you meet someone, whether your core values are shared or not, you'll know pretty instantly. So just knowing who you are and what you stand for and what's important to you and come to the table with that will help you identify those who will be the best match to share those with you. Awesome. Well, thank you for joining us and shedding light on this topic if there's anyone out there that wants to do the reverse that they are recovering workaholic. Figure it out how to balance both, then we would love to have that conversation too, but this was really great. From someone that is very career oriented, that I loved your story of how you were able to see the light at the end of the tunnel that you can make time for everything. Absolutely. And I hope to meet a partner who I can share that story with. You know, when I see your career oriented, when did you crack? What did you change? Any very work life balance gentleman in Florida, that's a call out for you. Caitlin is ready to meet you. She's new and she's single ready to mingle ready to not date a workaholic, but someone who is equally as enthusiastic about life as she is. All right, just saying. And career by did, yes. At the same time. Okay, well, thanks you too. Thanks, Caitlin. Thanks for all of you for listening if you enjoyed this episode. Please leave us a 5 star rating in Apple podcasts, reviews, and also little love note we always love that. And with that said, we're going to wrap this up. The dateable podcast is part of the frolic podcast network find more podcasts you'll love at frolic media slash podcasts. Want to continue the conversation? First, follow us on Instagram, Facebook, and Twitter with the handle at dateable podcast.

01:15:07 - 01:16:49

Tag us in any post with a hashtag stay dateable and trust us. We look at all those posts. Then head over to our website dateable podcast dot com. There you'll find all the episodes as well as articles, videos, and our coaching service with vetted industry experts. You can also find our premium Y series where we dissect, analyze, and offer solutions to some of the most common dating conundrums. We're also downloadable for free on Spotify, Apple podcasts, Google Play, overcast, stitcher radio, and other podcast platforms. Your feedback is valuable to us, so don't forget to leave us a review. And most importantly, remember to stay dateable. Too many things in our lives required too much effort. But when it comes to disinfecting surfaces with the new Clorox disinfecting mist, you just spray and walk away. No wiping required. The aerosol free Clorox disinfecting mist kills 99.9% of germs on hundreds of surfaces with an easy to use continuous sprayer. And it comes in two delightful scents with a reusable sprayer and refills that help keep plastic out of landfills. Try the new Clorox disinfecting mist today. Use as directed. Rinse required on incidental food contact surfaces. As long as I continue to make everything look pretty and shiny on the outside, I didn't care how miserable and ugly I felt on the inside. I realized that I deserved a better me, so I can be the wife and the mom that I really wanted to be. If you're ready to get real about addiction treatment, call Karen, a recent independent study showed that 94% of Karen patients were still in recovery 90 days post treatment. Visit CAR ON dot org slash real, Karen. We'll results real care, real about recovery.

Hello, Friends. Welcome back to another episode of the date will podcast. We are back, back, back, and the first two episodes of the season have been so stellar. We're so happy to get the feedback. We've been getting some of you have said they've been. I opening life-changing super insightful, so we're going to keep it rolling. We are. But I'm glad this week we are keeping it rolling in the sense of eye opening and life-changing, but it's a little lighter. I feel like we got a little letter tone. We have will who's going to be taking us through? Meeting his current wife on a solo trip. Solo travel in we did a poll in the Facebook group of the topics that people wanted the most the season. The number one topic was. How to meet people in real life. I feel like we are just starving to be people in real life after this pandemic. Starving is an understatement on one side wanting to connect with humans and in the other side. Forgetting how to communicate and connect with humans. I'm definitely struggling with the latter. I went to something over the weekend and I was in a crowd and Julie, I almost, I almost ran out of there. I didn't know what to do. I didn't know if I was supposed to say hi and make eye contact with people. I really felt out of my element. Yeah, I went to a concert recently. Oh my doors. And it was a lot of people at once. There were also a lot of teenagers. You apparently get an ex on your hand. If you're under 21 and they started marching. Oh my God. 90s grunge is back for teens. Okay, have you watched euphoria at all? I have not. I have not heard of it. All right, so if anybody who watches euphoria, you probably walk away thinking, oh, teenagers are like that. And then you look at the actual teenagers in real life, and they're all like pimply face, little dorky dipshits. You're like, oh, okay. Teenagers aren't actually like what they portray on TV because on euphoria, they're probably like 30. Trying to play 16 year olds. I forget that. It felt old as fuck. That's for sure. But it was good because music is important to my partner, so I was being a good girlfriend at going to this concert. What was the concert? I don't even know. That's how much you care. That's me too. I forget their names. That's like when I go to basketball games with my partner. I'm like, who's playing? I don't care. Okay. And my defense, he bought a ticket to this music festival and a lot of the people where I know it's. So it wasn't even like he went wanting to see these people per se. Oh, I see, I see, okay. But he probably likes the undiscovered. Yeah, exactly. Independent artists. No Rihanna kind of thing. Yes, okay. I get you, girl. I get to. I think the only crowd I can be around is a stand up comedy show. I realize I really miss that. And last night, Julie, I almost texted you because I watched Bernice E on it. On a virtual improv stand up show where it's called first impressions or something like that. And after everyone goes, you get to vote for them. So then if they win, they can appear on the next rendition of that show. So she won. She was one of the four winners. And she gets to appear again in the next show and she's phenomenal. I forget, I'm so happy we had on our show. We've also had people write in and say, thank you for introducing us to Bernie's. She's so funny and just so insightful and just very likeable person. So I would watch her in person. Oh, for sure. For anyone that forgets that episode, it was the pressure to settle down. And it was all about how you're leftover past the age of 30 and China. And she's hilarious. It was the lighthearted comedy that we needed on a very deep cutting topic, I think. Yeah, and I went down this stand up comedy rabbit hole because I crave it so much. So our guests for this episode will Rocklin is also a stand up comedian. You can find his material on YouTube. And I just watch all his stuff. I just went, I just went through it all. You know, like hours of it. And fun fact he is a friend of you as her friend's husband. I think you said you were like, well, we talked about we were brainstorming.

00:05:01 - 00:10:04

Okay, people really want to hear these IRL meet these be cutes to try to get inspiration of how we can meet more people IRL. And you said that you had the perfect guest because another thing we had talked about was the rise of solo travel. Especially after the pandemic, we're travel has been taken away from us. For so long, we feel like a lot of singles are just gonna be like, fuck it, I'm going anyways. By myself, I'm good. And this is the perfect opportunity to meet people. So this was the best hybrid of those two topics. And he's humorous, which I love a sense of humor. He makes my friend very happy. So I'm a big fan of wills, but this is the state that we're in. It's like trying to get creative with how we meet people in real life. How do we find that human connection? And as life goes on, you never know what a throws at you, so I guess that's my transition to you, Julie. How is the egg freezing going? I was gonna give an egg crazy update, but you know, day 7 right now, hopefully we'll see tomorrow when I go back to the doctors. Hopefully my last day of meds is tomorrow because it's 8 to 12 days and it's all about how you're responding. So so far I've been responding really well. So I'm hoping that I'm on the lower end because that means less times I need to put noodles into my body and less medication costs I have to occur. So I'm really hoping that tomorrow they tell me that I'm good to go for the procedure on Monday. So this is something I didn't know before you pay by the day for the medication. So the longer you have to be with this process the more you have to pay. So you're hoping for shorter days exactly in this process and that's what you mean by the lower end of the yes. Thank you for clarifying. Yeah, I ordered 8 days of beds instead of 12 with the hope that I wouldn't need them. So yeah, things are going well. I had one day that I felt really low and I definitely was pretty hyper sensitive to some things my partner said. I think all the stress of just a lot that's been going on in our world to came to a toll for me. I believe it was the hormones kicking in. I don't know for sure, but it probably was. But outside of that, honestly, I haven't felt that bad. There's been some days I've been extremely loving. And maybe it's the hormones kicking it in a positive way. But the shots really haven't been bad. I hate saying this, but I feel like I don't know if I could have done it myself. Maybe I could have maybe I would have risen to the occasion, but I think having my partner support, it has brought me closer to him. You have to do it in your belly, which is the area of my body that I think I'm the most self conscious about. So I'm like, there's something extremely vulnerable about grabbing your belly fat and being like, put a shot at it. So it definitely has taken things to a different level. That's for sure. Yeah, definitely another level. Are there things that you can't do while you're going through the shots? Like, can you have sex? No. You can not have sex. We wanted to ask about other stuff, but honestly, I was a little embarrassed to ask. Can you go to? I couldn't break myself to ask, and then I thought about doing it for research for this podcast, like priming it that way. But I still couldn't break myself to ask. So at this point, I think just abstaining, but also heavy exercise, yoga and Pilates specifically because you're twisting a lot. Oh. Even running and biking is on the edge. They said you could do it, but you need to be careful. So I've just been laying low. I don't know, a week to, as an excuse, not to hold myself accountable for exercise. No drinking, I'm guessing. You're not supposed to drink. You can do one drink a day. Like a glass of wine, but I've just been abstaining from alcohol because I just don't want to risk it. One of my friends definitely drink during it, and she said that she had stomach cramps so bad that she had to go on meds for cancer patients. So what? Yeah, and she doesn't know if it's from the drinking, but I didn't want to risk it, so. Shit. Yeah, I actually stopped drinking even like a week before this whole thing. To just be really careful. But yeah, all is well. That's the update. We'll keep you posted next week and then hopefully I'll be done with this whole thing. Fingers crossed. I think it's kind of funny that you were embarrassed to ask about the second question. So why is that Julie? I don't know. I mean, you're a grown ass woman. I know. I know we do a little fingering. Can we do a little? Well, let's ask what I just couldn't break myself to do it. So if anyone knows the answer, write it, please tell us. Maybe I'll grow some maybe I'll have a grow some bigger vaginas. Is that what was I going to say? I was like, I don't like using gross balls.

00:10:04 - 00:15:05

I hate that. It's just a gross term. But bigger clit and ask the right questions. I mean, aren't I doing that, but. Anyways, that's the update. I wanted to ask you you a going kind of back to our topic. I was curious, have you ever met someone on a solo trip? Or on a trip in general? Like someone romantic. Oh yeah. Yeah. Okay. I had a whole relationship with someone in the UK. I do remember that. I actually do remember that. And then you got back and you're like, no. No. So it was just so wild. I went to the UK for work, and I was filming a show over there. And I went on Tinder just for funsies. So I'm really into John Cusack for anybody who doesn't know. John Cusack, I would leave my partner in heartbeat for John Cusack. It's a known fact, okay? He knows, I know. The whole world knows now. And I met a guy on Tinder named Jim Cusick. And I'm like, close to that. James Cusick, they went by Jim. And I was there for three days. We had a three day romance. We did the whole thing, like we went on dates, and we asleep over. He met my coworkers, and then I had to go away. I had to go to another part of Europe for a few days, and I came back to London. And the whole plan was when I come back to London, we meet up again because there was something so special. And I think as soon as I left, I already knew that this was not going to be anything special. But he was willing. He was willing to move to the U.S. willing to have me move there. We had this. We had this fantasy romance that was really wonderful in the moment of the place and time that it happened, but definitely was not a reality once I left. Was that the only time that happened or did you have other times? I think that was the only time that it was like a very substantial romance. And that was the closest I'll ever get to talk yourself. You never know what John Keith sack could be listed right this minute. I'm ready for you, John. I'm so ready for you. You know, I have actually never had a vacation romance before. Ever. Not even a hookup, nothing. And I think it's because I'm way too logical with some of this stuff. I think it's that. I know what it is. I viewed it as a waste of time. I was kind of like, well, the odds of this turning into anything is slim to none. So if I'm going on vacation, I want to experience the trip that I'm doing. The experience would be with the people I came with. I think I can pardon mentalize a lot. And I like that this story that we're hearing today actually proves to be wrong that you can make something happen. You just don't know where life is going to take you and every opportunity to meet someone is an opportunity, whether they live in your city or they live a zillion miles away and what was ironic too will get into the story is that even though will and his what now wife met in Europe, they had a lot of cross connections. They had a lot of cross connections in San Francisco and New York and there were so many, it was like this really is a small world. And I think we forget that sometimes. It feels so random to me that I just I can pardon mentalize it. I think that makes a lot of sense, but at the same time, what I really love about meeting people on vacation is that all your expectations are thrown out the window. Yeah. And you don't have any pressure on anybody. In dating in real life, I feel like a lot of us are spark chasers. We're chasing that spark as a subscriber yet spark on this date. But when you're on a vacation, you don't give a fuck you're like, I just want to meet someone who's local, have a good time, and I feel like that organic chemistry can happen a lot easier in those situations. But I agree, logistically, it's not as viable, but we've seen it happen and it could always happen. Yeah, I think just keeping it open by doing what's right for you. And if you're on my boat, maybe after you listen to this, you'll have a different perspective, and that's what data was all about. Yes, opening up your perspective. Should we get to our question? Because I'm dying for this question. This one's so good. Let's do this question. This listener wrote in and said, I'm having a hard time being single. How do I embrace singlehood as much as some other people like to? Yeah, we've talked about this too. I think there's a difference between embracing singlehood and there's also this way of thinking about embracing where you are today is where you're supposed to be. I think it's not so much about embracing the fact that I'm celebrating, I'm single, look at me, I'm a single independent woman or a single independent man.

00:15:05 - 00:20:13

It's embracing the transition or the state of being that you're in. And one of the best ways of embracing this phase in your life is to think like, what are the things that I get to do while I'm single that I don't get to do when I'm in a partnership. And I think one of those for me would be everything being on my own time. You know, I can do whatever I want whenever I want without accommodating someone else. That is the freedom that you get to experience when you're single. I was just pulling up a post that coffee meets bagel put up the other day. And it says both are true. Being single sucks and, being single has unique things I can't do in a relationship. Getting ghosted sucks and getting ghosted has nothing to do with me. Breaking up sucks, breaking up gives me a chance to move on to something better. Rejection sucks. Rejection is not going to stop me from trying again. So what I like about this is that you can feel like being single sucks. That's fine. That's natural. And if that's what you're feeling, we don't want to ever tell you to not feel that way. That being said, can we push ourselves to think of the positives, the flip side of it, what you were just saying, you a's. What do I get out of this state that I may not be able to do in the future? I think one of the things that I love when I was being single was just having time to myself. That I don't really feel like I have as much anymore. And it's not that it's a problem now, but it was a phase of my life that I did a lot of self work and self development and actually quite frankly set me up for where I am today. So instead of looking at it as a status you need to fix, how can you make the most of the time that you are single? And I believe Chelsea handler puts something up to about this that really resonated is that she said you know that she's with Jo koy Dow and she's so over the top happy and for years she was just like, I'm gonna be single. I've accepted I'm single and she's now saying I finally met my person and the irony was that he was there the entire time. But she got to a place in her own self and same, I'm sure he did grow too that got to them together. And she had a video up that said the single most important thing you can do while you're single is becoming the best version of yourself. And that doesn't mean that you need to be perfect or you need to be X, Y, and Z that you're not. It's just how can I get a little better every day? And what we've said become the person that you want to date. And I think if you can embrace singlehood as a season and not that there's a flaw with you, there's something wrong. It's just where you are, current day, and what can you do to make the most of it? Normally, people like to view singlehood as a transitional period in between relationships. It's like, oh, I'm on my way to the my next relationship. So I'm single during this period. What if we switch the thinking and think about relationships as the transitional period in between us finding ourselves and having a relationship with ourselves. So it's a state of being that helps you understand yourself more in relation to the rest of the world versus like you seeing the world in relation to your partnership, right? So I think it's just like the shifting that mindset and thinking about this as you're exactly where you're supposed to be. Yeah, I mean, there's been so many times earlier in my life that I felt like there was something flawed about me that I was single that I wasn't in a relationship that that was the coveted goal. And it took me to really sink in that this was precious time that was just as good as being in a relationship just in a different way to get to the place that I think I did actually attract to healthy relationship because I wasn't coming from a place of desperation or trying to fill a void. And the reality today too is that life isn't linear with relationships. You're not single and you're married and then you've kids and then you're with that person forever. There is a chance that you could become single again. We have tons of people that are divorced or widowed or whatnot. I think the best thing you can do for yourself is be happy no matter what your relationship status is. So if things do change for some reason, you could pick yourself back up. Yeah. I much rather be single and thriving than lonely and in a relationship. Exactly. Okay. So many good things in this episode, so I'm glad that we're getting into it quick announcements. We mentioned last week that we have love in the time of Corona, public group, and then the sounding board, which is our premium membership group that every week we have these weekly sound offs where people of the community can connect with one another. We had a really good office hours last week that UA and I did and we definitely deep dived about love is blind for a while and then we got into people's burning dating questions and it's not just us giving the advice it's the entire sounding board coming together to support one another.

00:20:14 - 00:25:05

So if you're looking for that support, the hardest part I think about being single is that it can feel really lonely at times. So if you have the support system, maybe it won't be as big a deal if you're single. If you're interested in that, join by going to data podcast dot com slash sounding board. We put a PSA last week that if you've requested access through the Facebook group, it's not that we're rejecting you because we don't want you in there. You just need to sign up first. So that's the biggest announcement this week. And share this with a friend. That's our other announcement. Okay, let's get into a few quick messages from our sponsors. This episode is brought to you by switchcraft. Have you noticed match three games can all seem like the same? Don't get me wrong, they can be a lot of fun, but they all tend to have the same format, which gets boring, but switchcraft as a brand new take on match three games. As you play, you unlock pieces of a beautiful, magical and gripping graphic novel. The game is a unique blend of TV worthy writing, choose your own adventure style narrative and thousands of magical match three levels. My favorite part of switchcraft is the inclusivity and diversity of its 85 characters. It's 2022, and it's nice to play a game that features a majority bipoc main cast of characters headed by a strong female lead, wider diversity, including nationality, sexuality, and disability is embedded throughout the story. It's such a refreshing take on your traditional games, and I'm all for it. With switchcraft, play your way through hundreds of enchanting match three levels, revealing a dark and winding mystery story. It all starts with a disappearance of your best friend. Now it's up to you to unravel the mystery of her disappearance using your magical, match three skills. Get playing today, download switchcraft for free and unlock the magical mystery. Okay, let's hear it from will about solo traveling. Solo travel. Solo travel used to be the thing you do when you have crossroads in your life or you just graduated from college and you want to take a few months off before you get into the real world, but we've decided and we found that in 2022, it's a new trend for singles to do solar travel as a way to not only get themselves back out there on vacation, but to meet other singles who are also solo traveling, but our guest today will dissolve travel before it was a thing. You can call him the grandfather of solo travel. Just kidding, you're not. They've been doing solo travel for a long time. But will has such a great story about how his solo travels have actually led him to his now wife who's a good friend of mine, so welcome will to dateable. Thank you so much. It's great to be here. Hello everybody. Well, welcome. Welcome. Will has been in LA for a year originally from New Haven, Connecticut. He's 39 years old and he is married. And so let's talk about solo travel. You had a trip that changed your life and you didn't know this was going to happen. So let's just talk about where did you go on this trip? Let's start with when, when did the strip happen? This was way back in August of 2016, a fond time to remember when all of today's problems didn't exist. It said, where did you go? I went to the Italian Alps, a place called the Dolomites. And then how did this trip come about? How did you decide to do this on your own? Yeah, so I was in San Francisco living there at the time, beautiful city, but I realized it's not for me. And I wanted to go back to New York and I was thinking about specifically like my job is kind of run its course and I've done everything in this town that I've wanted to do and around San Francisco. And I just had a sense after dating a while that my person wasn't here. I could just kind of palpably feel it. They're not living in San Francisco. It was sort of intuition or gut or whatever you want to call it. And I was like, oh, I should also just play the odds and if I'm looking for a nice Jewish girl, which I was at the time, I should obviously go to Brooklyn. So that's where I was on my way. The Mecca. I carved out like 6 weeks to travel and hang out. So on Thursday, I quit my job on Friday. I moved out of my apartment and on Saturday. I was at Burning Man. Now, this isn't a story about meeting your person at Burning Man, and that would be cool. That would be like a groovy place to meet your person and the team. We've done that story too. Yeah. Yeah, yeah, yeah. But that's not this story. And I don't want to knock that story. That story's great. So I decided after Burning Man that I wanted to be alone because I will have been in all this commotion and activity and involvement. And so let me just go throttle it down and go to the mountains. That's my happy place. And I've always dreamed of going to the dolemite. So this gorgeous mountain chain in northern Italy, and I really wanted to just check it out.

00:25:05 - 00:30:05

So it took me from BlackRock city, like two, three days together because it's like one remote place to another remote place. And yeah, I was alone, and that began my 6 weeks of European travel alone. Okay, so 6 weeks, how far in did you meet your now wife? It was pretty early on. I met her. I think just a few days into the trip. A few days. Wow. Yeah, how did that go down? Yeah. Let's talk about that. Yeah, sure. So when you get to the Dolomites, it's like a bunch of 50 year old German couples who are there for hiking. Perfect. And I was like, I was the only single ish looking person floating around that I could tell. And I checked into a bed and breakfast, not an Airbender breakfast, like a regular one. And I picked this place like weeks prior because it had like a spa and a sauna and a steam room. It had like all these really nice amenities. Because this hotel in this town is basically a ski town, okay? And in the summer, a picture like a sound of music place where the hills are alive with the sound of music. After a couple days of hiking or a day or hadn't been there long, I was like all tired and I was like, let me just chill out and enjoy the spa. And I get down to the floor and German couple German a couple of German couple and then one single woman who is now my wife and so she was born in China and at the time I had no idea if she spoke English if her husband was upstairs. I don't know what was going on. But you didn't know she was single. No, but she was alone. She was the only woman alone that I had seen in days. And so I was like, well, she's attractive. Let me not creepily see if I can be near her physically without alarming her. That sounds creepy. Listen, I'm in a towel. She's in a towel. It's ripe for being creepy. And I knew that. And it took everything I had in the tank, not to make it seem creepy. Now, I don't want to say how this ends, but I was successful. So let's not knock. The towel worked. The towel trick work. For now, she was a bigger creep, so it worked out really well. Bingo. My wife is also creepy. It's all you need is two people at the same page. For every pot. Lid for every creepy pot. Yeah, so now she had heard me talking from across the way. And I was doing my thing to people who didn't want me to be talking to them. You know, when you get in the spot and you like chit chat and they're like, leave us alone. So I left them alone. And I was like, you know, cruising around and she was in that area where you kind of chill out, like it's lounge chairs, and there's magazines and stuff. So there's like not active spawning happening, you're kind of in between. And I really wanted to talk to everybody. I didn't want to be like, hey, what's going down? You know, so there was this very wacky shower in the environment and it played music and had a LED light show. I think it even had like a perfume component. It was an amazing Italian invention. I've never seen one before since. And I was like, wow, I really hope she goes to use that shower because when she comes out, then I'll hit her. It'll be intro. That's the line. What line was in your mind that you thought this was the perfect setup? Now, before I tell you, I should tell you that I'm a comedian and a writer. So I really thought about it. And the line that came out was, how's that shower? Wow. Hey, sometimes that's all it takes. Sometimes the less creepy is the more straightforward. Yeah. Listen, it wasn't, you know, miraculous, that's not a great line. I know that. But yeah, as you put it, sometimes you just need to cut to the chase. It was an amazing shower. It was noteworthy. We're talking about it right now. And she came out, she's like, yeah, that was interesting. And I was like, you know, so we took it from there because now it wasn't about me and her, it was about a third thing. The shared experience that we'd had. And that's to get a little sincere, a way to not be creepy when you're talking to a stranger. Bingo. And then what happened? I took a seat on the lounge chairs next to her and we started chit chatting like, hey, you know, how are we both here? Why did you pick this place? This seems random. Oh, it's amazing. You speak English. I didn't know that. And we very quickly realized that we had a surprisingly large amount of things in common. We both had lived in the same neighborhood in New York and in San Francisco. Wow. We knew some people in common from Google where I had worked in the past and she was still there. Once a person was in common establish, then her radar became creepy anymore. Yeah, now you're totally safe. Which isn't exactly true, but you know, whatever. And so yeah, so we talked about all those things and they kept adding up and it was really, really shocking. And after about an hour or so of chit chatting, she's like, you know, I've been in the spa like kind of all day. I'm gonna take off and go have dinner with my parents. And I was like, um, date night. And so I invited basically out for a drink, and she kind of said yes, I think.

00:30:05 - 00:35:02

I don't think she said, no, I think she was like, yeah, okay. She didn't say no. So was a yes. Yeah, I'm pretty sure she said yes out, right? Maybe she didn't, but I think she did. Well, she showed up, so she said yes. I'm sure she did, yes. Yeah. Yeah. So she took off and she, you know, we exchanged info and she went out to dinner with her folks. But because she was with her folks, she was like, I met a new friend and they're like, does he want to come to dinner? So then I got a text inviting me to dinner with her parents, I was like, this is going way too slow for me. We can speed this up. So I was like, no, you do your thing and I'll go do mine and I'll see you later. And you know, so I'm backpacking, I'm not quite literally backpacking, but I'm effectively backpacking, I have a small suitcase. But in it, I brought one fancy article of clothing, which was a cardigan with leather elbow patches. And I was like, tonight's the night. You've been preparing for this night. Pulling out the big guns. Yes. Now, you should not bring that on your 6 week trip to Europe. That makes no sense. But for some reason I brought it. And I was like, this is it. When I was going to wear, I come down the stairs. She's already there in the lobby, and I'm wearing this camel colored cardigan with a white button down and jeans. And she's like in flip flops and shorts. And she didn't get the memo. Yeah, she thought it was nuts. So the crazy potential Ness of me continued. And then we went to the one bar that was open in town across the street and I had lived in Italy in college and I speak Italian. So this was like the nice, I was like, okay, here this moment's gonna be cool. And so I ordered an Italian for both of us. And she wasn't sure if I actually spoke to talent or if I was this like kind of being a show off. But then the bartender asked another question or two, and then I was like, and then she was like, oh, okay. And I was like, finally, my minor and Italian is paying off. And we had our drink and there was nowhere to go, so we ended up going back to my room because she was staying with her parents down the hall. So it also acquired this sort of like freshman year college. Trying to feel sneaking out. Yeah. Were my room by default. There's nowhere to go and we have a really nice evening and then she tiptoed back into her room later that night. And yeah, we exchanged info and so I think a few days she was leaving basically that the next day. And then I asked her if she wanted to meet up later in Europe because she was living in London at the time. So we ended up changing emails and stuff like that and picked her go to Copenhagen together. Our second date was effectively a weekend together in Copenhagen. Wait, so will back up for a sec, what compelled you to ask her out in the first place? Because it's kind of, it's still sort of uncomfortable, right? You're there on your own, you meet a stranger, you have some friends in common. You don't really know her situation, but you're like, fuck it, I'm gonna go for it. There's like a moment of choice. I think that you always have when you meet someone new of like, am I gonna like, let the fear win? Or am I gonna just go for it, right? What are we alive for? You know, I'm not in a towel and Italy with a vision of coming here to play it safe. There's nothing that could happen that's bad, right? Like maybe it doesn't go great. But I was gonna be, you know, watching Netflix in my room alone anyway. So it's like, why not? And when you first met when you were asking her out, was there this feeling like this is something romantic or was it more just what you said, the other option is up by myself? Well, it felt like kind of like we knew each other already. It was one of those. So I'm not sure how much trepidation there was. Either of our parts because there was just an eerie amount of things that were racking up really quickly in us knowing each other, including the fact that it was so crazy that we were meeting here, when we pretty much concluded that we had been at the same party at one point. She had almost gone on a date with one of my best Friends, there was a surprising amount of near misses. So I think that it wasn't a typical how do we steal ourselves for being with somebody who may be a waste of time or it isn't right. It was such like a full body yes, either as a friend for right now and the curiosity of what's happening or all the potential that has turned out to pan out. I get totally see that. You're like, there's too much coincidence here to not keep this conversation going. Yeah, yeah, we've all been in those moments right and you're like, wow, this is truly a gift from the universe. Let me see what's here. And there's that joy of that excitement that surprise you're unwrapping this gift. Yeah, there's a reason why you're brought together in that one moment in time. So now we're going to Copenhagen. What happens on this trip? Yeah, Cobain, what a great what a great trip that was.

00:35:03 - 00:40:12

She her playing arrived late and I wanted to go do something like I had a friend who lives there and she was like at a concert and she's like, come with me and then I was like gonna miss Amy's arrival. So I made like a little welcome basket of like snacks and things. 'cause I was like this is such a leap for her to come to me. It's still a stranger. And I was like, I need to warm the place a little bit. So she feels like really welcomed and cool. And so I just ran this really fun to Aaron, which I've repeated now, AD nauseam, so many times as a husband and that anyone in a serious relationship has done for their partner of like, let me get you a care pack. It's your thing now, yeah. Yeah. So I pull all these things together, not knowing her. And it was really fun. I remember pretty vividly being the striping, like, what do you want this or should I get the goldfish? Or what is this Copenhagen thing? Kind of piece in it together. So I make all this and I leave it in the room and I write our note and of course I told her like, hey, I'm going to go to this thing. And she's like, cool, I'll come meet you there. You guys are sharing the same hotel room. Yeah, we're in the same hotel room, yeah. Oh, it's serious. I gotta ask 'cause I'm so curious. Did you kiss or did things go down the first night? Yeah, well, you skipped through some stuff. That's the stuff I want to know personally. Is this a PG podcast? Oh my God. This is borderline porn. What do you think you and I are doing over here, right? Since you asked, yeah, you can just cue the bouch out thing. You can just play that in your mind. Like, okay. It wasn't. We weren't trying or planning or I had no hopes of doing that. I'm actually a little like prudish, maybe you noticed because I left this whole story out as part of the story. You got caught up at the moment. But yeah, we had this really beautiful kiss in the stairs of the hotel. It was like a really nice staircase. Even before she came up to the room, it wasn't like we like towards others closed off when we got in there. It was just like, we were just kept hanging out and felt really, really nice and then it was like, you needed for the kiss and that felt good and then everything felt good. So we just kept going, basically. And yeah, and so then in Copenhagen, there wasn't a question about one rumor too. That was already established. I mean, I figured as much because after one night to, you know, I mean, did you derail your trip? Were you already planning going to Copenhagen? Or was this kind of a deviation? Because of her. I had the no plan plan for chunk of it. Beautiful. I love doing that. As long as my anxiety can hang on, 'cause I definitely have a lot of that and want to make sure everything's going well and smooth. But there was a large amount of it that I left totally open to fate. So I picked copying because I knew it was a good flight for her and for me. There were some other options I was looking at and they were all harder for her. So I was like, let's do Copenhagen. I don't know if we established this yet. She did live in London at the time. So she wasn't exactly like traveling from the states to go to Copenhagen. Just wanted to clarify. But still going somewhere to meet you. There's still a clear level of intent that's happening there. I guess I get this point to both of you think this was something or was it more kind of just, this is fun, let's see where things go, because you still live at your planning on moving to Brooklyn, right? So it's like what's going on in your mind? I think it was just at this point, this is so fun. This is so exciting. This is really special. This is rare. I can't think of many or any time so that this has happened. How can you not follow up on something like this? What would hold you, again, that same, why wouldn't you feel this out? We had such a connection. It was so clear. And so wonderful that I never thought really twice about it. And I think that just by establishing a place that was easy for her and making that clear and her understanding that and being appreciative of it, it started to reveal who I was and what I, you know, not just words, but actions. And it's such a big deal for two people are trying to figure out who each other are. And so some of these things that can take weeks or months to surface showed up really, really, really fast for us. And we skipped the part not only was there like a fun night of romance, but also I ended up meeting her parents the following morning at brunch and she was like, oh my God. This dude told me he was gonna go on an early morning hike and here he is coming down the stairs. She's like, don't come over here. Don't come over here. And I'm like, oh hey. I guess I gotta go over there. There's no playbook for I hooked up with your daughter last night. Let me meet you right now. Yeah, it's more awkward if you don't go over, but I could see it being super awkward to also go over at the same exact time. Yeah, now this is the moment. This is that fork in the road where I feel like a lot of people would have gone the way I did not go, which is like, I can just kind of like shirk over here and like why do one of these and just hope this goes away soon, but I was like that doesn't feel right.

00:40:12 - 00:45:10

I gotta go in. I gotta say hello. Did her parents put the two and two together later? You know, we don't know and I never want to find out. That is something we have not ever talked about at Thanksgiving dinner. Yeah, yeah. I mean, they're Chinese and there's some cultural things that will never iron out because of that. And I would love to keep this as one of them. I just never want to ever know what they thought. So bring us back to Copenhagen. Yeah. How long is this trip? What's going down, how are you feeling? Yeah, it was a weekend. I think it was a long weekend in Amy had, she was coming in from work and cheating a little bit and working on the plane and then cabs and stuff. And it was amazing because I knew what I would like to do while exploring a new city and that's kind of like walk around, check out the neighborhoods and maybe go to a museum if that's cool, like eat some stuff like a mix, like maybe rent a bike. I don't know. That's kind of what I would do in Copenhagen, right? And then there's this other person with me that I have no a little bit pretty well for how long I've known her for sure, but I didn't know anything. So I kind of like try to make her feel welcomed and comfortable as you heard. And then also kind of just bring her along and what I thought was cool. And then when we were together, let's kind of horse trade or what do you like and we'll do that. So she just kind of jumped right into the pool and I have to give her so much credit for like throwing a lot of caution to the wind and being open and excited and ready to try things. So she got to the hotel, she saw the basket and the little note and she was pumped and then she took a cab to meet me at this not touristy place like 20 minutes outside the city where like a punk band was playing because that's what my friend from Copenhagen thought would be cool. So now Amy's dealing with, you know, and I'm a huge music fan and I go to see shows all the time, you know, this is like before COVID. So now she's getting into the deep end of something I really love to do, which is like not tours travel, hang out with locals, do music, and she's like way into it. And I was like, um, this is interesting. And then I booked a really fancy restaurant for lunch the next day because Copenhagen has some Michelin stuff going on there. Nice. And I remember asking your really innocently, I'm like, are you into food? Amy is like one of the most foody people alive. It's like her main thing. And she was like, yeah, yeah, I am. And it was like a heat wave and Copenhagen. So everyone's trying to get to the beach and the restaurant calls us and they're like, are you sure you don't want to cancel? 'cause if you do, we all get to go to the beach and I'm like, nah, sorry. We're coming in. So it was just me and her as if we rented out the restaurant. And it was like 18 people, including chefs and waitstaff just for us. Just for you too. It's so fascinating to me because I have personally never done something like this. So I'm just blown away, but when you think of couples travel, usually it's when you're far into a relationship. So you kind of know what the person's into and what they like. And it's so fascinating that you were just saying that you asked if shoes to restaurants that were pleasantly surprised she was. At this point, I'm still trying to piece it together, but are you feeling like this is going to be something or are you still just going with the flow at this point? Just going with the flow, yeah. I don't even evade your question. I'm so sorry. Just doing my thing having fun being present, you know? Because in between those, you know, like all the problems I left in San Francisco and all the things in front of me in Brooklyn. I was just super present. I had no pain. It was the most like Buddhist I've ever been because there was only right now. And what was the general vibe of the weekend where you two kind of romantic and coupling? Yeah. Yeah, it started to go there. Like there was some hand holding. I remember we went to this. We went to a bar and I got some drinks and I turned around and some dude was hitting on her and I was like, you need to leave. So I got to like be protective and kind of do that gently as I could. And we rode bikes together. So there was like a cialis commercial moment or two. So when the weekend kind of comes to an end, what's next on your agenda? So you just kind of like, yeah, tell us. Yeah, so at this point, I was like, you know, I finished up my travels and then I got very focused on getting settled back in New York and hit my job and stuff like that. And Amy was like, oh my God, what's going on? What's happening? So the storyline starts to make me look less good for quite a while. And I become a little bit more careful and unsure about what's happening because she's in London and I just got to New York and I'm supposed to start this startup and be super focused on that.

00:45:10 - 00:50:04

There is a visit. I go to sorry, I go to London where she was living and that was really cool. We had a cool weekend together. See if I remember the timeline. But anyway, there was one trip where I go to London and then there's one where she comes to New York and she came to New York around my birthday and she met a bunch of my friends, which was really cool. How did you introduce her to your friends? Did you tell all of them the backstory? Yeah, yeah, I was like, here's what happened and we made a birthday dinner. Me and my friend and Amy was one of the guests at the dinner, basically. And she was staying with me. And she had friends in New York as well that she was hanging out and seeing. But I think there was a little like, I don't want to tell will I'm in New York just to see him. So let me couch it as I'm going to hedge and see some other friends or whatever. So I remember that being in the air. But it was easy to bring her around and show my friends and have her meet them and stuff. There was no hidden agenda or hiding behind what was going really, really going on. Okay, let's hold that thought for some messages. This episode is brought to you by drizzly. If you look for it every day has cause for celebration. Celebrate a friend for their promotion, baby, wedding life thing. Celebrate yourself for keeping the couch warm. It's no easy feat, especially if it's a big couch. Or maybe you just want to celebrate living in 2022, where you can get beer, wine, and spirits delivered from drizzly in under 60 minutes without leaving, said couch. No wonder drizzly is the number one app for alcohol delivery. And remember to share the love, you can get alcohol delivered to your friends and your coworkers, what a nice surprise. Right now, drizzly is giving all new customers $5 off their first order with the code fast 5. So download the drizzly app or go to drizzly dot com that spelled DRI Z, LY dot com and use the promo code fast 5 that spelled FAST number 5 for $5 off your first order. You're welcome. Have you ever thought about how much better dating would be if you had a whole army of people supporting you along the way? We know that dating can be frustrating and lonely, but it can also feel fulfilling and fun. Have you recently decided you want to make some changes to your love life? Maybe you've recently reentered the dating scene. Maybe you've gone on one too many dates that went nowhere, or maybe you're just ready to take your current relationship to the next level. That is exactly why we created the sounding board, a true extension of our podcast that delivers a personalized experience, which includes monthly office hours where you can drop in and chat with us about anything. Weekly sound offs with guided discussions and regular virtual happy hours, allow Julie and I to become your dating sherpas to provide real-time guidance and wisdom in a more intimate way so we can all navigate dating and relationships together. Join the sounding board today by going to dateable podcast dot com slash sounding board. Again, that's dateable podcast dot com slash sounding board. So okay, so just I love timelines UA knows this. Oh yes. Follow over long. So you meet and then how much time is between now going to Copenhagen from that first magical night? I think it was about like a week or two. Maybe a week. And then after that you traveled for another four weeks. And are you guys keeping in touch during this whole time? Yeah, yeah, we're texting we're staying in touch. I'm sending our photos of where I am and stuff. So yeah. Okay. And then you go to New York, so that's like 6 weeks later. And when did these visits happen? I think the next trip was her coming in New York in December, the end of December. And then she was there for maybe a week and then we decided to go take a trip together and spend new year's somewhere. So we ended up going to Bermuda. That was pretty cool. And then I remember at the end of that tripping like, what's happening? Yeah. What are we going to do here? Not only are we an ocean away, but you are also ready to change your life. Like you're wondering what's next for you from a career standpoint and you're thinking about like doing some soul searching and solo travel like, I don't want to get in the way of that. I'm not going to derail you. And that felt really important to me. And it was sincere and also kind of connected to, I don't want to be in a long distance relationship, like that's not exciting or I've been in those and I'm cool. I'm good on that. So I don't know, thank you. What did you want, will, at this time, were you looking for a long-term stable relationship where you looking to find that nice Jewish girl to marry? Yeah, I was ready to find the one. You know, that's why I left San Francisco, right? I was trying to find her. And I was like, not really thinking this would turn it into it, just because of like timelines and locations and I think the right person in the wrong moment isn't going to work.

00:50:04 - 00:55:02

So I was feeling maybe a little bit not sure or maybe even pessimistic on the odds of it panning out. And like, did you want it to? And it was just the, you know, the situation, or were you just kind of like, this isn't a viable option because of the situation. Yeah, I was pretty in my head on it, and I was like, this is let me let the brain solve this one. And the brain's like, you're far away and about to do all these things. So therefore, it does not compute. I don't even know if I got to the point where I was like, what do I want? I wasn't really thinking with my whole being and I didn't learn how to do that until it really Amy was like, the first time in my life where I'm used my heart to make a life decision. And we can talk about that later because I ended up happening later, but this was the beginning of the winter of our long distance, basically. And she wanted more, right? I think she was, yeah, she was in. She was like, because Amy was using her heart. She knew how to use that. And I was in kindergarten on that one. And she knew in a couple of friends of mine picked up on it. They were like that girl at this birthday interview. She's in love with you. Yeah, she's not coming to New York just for shits and giggles here, right? So there was a long period of uncertainty between you two. And I remember her telling me because Amy and I went to Copenhagen together. So we also shared this experience, though we did not hook up, so I'm a little mad about that, but she and I talked about you and she's like, I think we're just in a very uncertain period right now. And I don't know if we want the same things. And I think she was saying that really to protect herself because she had mentioned you so many times and I think it was just in her mind fate had brought you two together. So the winter of your relationship is happening, like you said, what helps you to get out of this slump that you're in. It was a combination of things, but one thing that really stands out in my mind is I would go on dates in New York or I would see somebody for a week or two. And then Amy and I would get on a FaceTime and I would feel so much more through this piece of glass. And just be like, wow, this is really special. This is like, this is something I'm not thinking about. It's just happening. I'm really smiling a lot. I feel so easy in being and talking with this person. And that was just impossible to ignore. And when I was most hesitant in the beginning, she was kind of most clear and then we kind of flipped, she did have a passenger and all this self. What's a pasta? Vipassana silent ten day meditation? Oh. And she did a yoga teacher training, like she did an eat pray love thing for a little while. And that turned her inward and then I became sort of important or uninteresting or whatever to her, you know, reasonably. And right around that time, I felt something like this needs to change. I'm need to get reacquainted with her. I need to do something. And Julie, since you're a timeline person, I think we're now around. Thank you for addressing that. I'm trying to be a good guest here. Maybe around like may. Okay. Don't hold me to that, but around May. Because if you have Amy on and she's like that timeline's wrong, I want to be clear, whatever she says is more correct. But we both had reason to be in San Francisco, me for a bachelor party and she for a wedding. So we decided to be together in the middle and that she invited me to this wedding as a guest. So I'd be like her date. That to me that came with all these things like, oh, we're back on. Here we go. And I remember her calling me like a kind of two days before, and her telling me that we were friends now. Then that was what was going to happen. We were just going to be Friends. And this was an invite as for fun. And don't expect, don't expect anything. Do you think it was that because you weren't fully committing to doing this with her, that she kind of went to self protection mode or even not even self protection mode, but just this isn't the right person because they're not stepping up. I don't know, maybe. I don't think it had anything to do with me. If I had been ready to roll in the beginning, that would have changed things, of course, I think, but I think that she had her thing to go do and her herself to go explore and she had big questions in front of her that exceeded me and had more beyond me. We're beyond maybe what she knew. And I'm not even sure if she would say that to you, but that was my assessment. And I really didn't want to get in the way of that. I don't want to derail somebody from what they wanted to figure out who they want to be. How did it make you feel when she said, we're going to this wedding as friends, don't expect anything. Fucking furious. Can I swear? Yeah. I was super, super fucking. I was on 6th avenue at 13th yelling back at her, like, what are you talking about? What does this mean? You're like pulling the wool over my eyes. Gaslighting. Other phrases that may or may not make sense, but I was really angry.

00:55:02 - 01:00:03

I was like, what do you mean? You're telling me this a day before, like, I'm about to get on a plane and go to a wedding and do the wedding coupling like performative dance a little bit with you and you're now like piercing that bubble. Why would you do that? That was the first time I got mad at her. And it was adorable and retrospect. According to you. She was surprised. Yeah, according to me. She was surprised that I was mad. And I remember being like a little weird on the plane and being like, what am I flying into? Mine idiot. Is this like a waste of time? And I got to the airport. Kind of like cold and standoffish, and she gave me, she was like, hey, hi, you know, a huge big hug and gave me a kiss on the lips and I was like, we're doing that. We're kissing on the lips. Like, what? What's going on right now? So I was really confused, and then we had a good time at the wedding. We had an okay time in San Francisco, but generally pretty good. Why just okay? It just wasn't in sync, you know? Like we weren't feeling. It wasn't butterflies. It wasn't super lovey, dovey. Just even like logistically, I'm like, hey, we were going to be at the park here and you're not here and you're running late, and it feels like I'm not that important or this, you know, like that stuff. That stuff's not like insignificant in my book. You know, if you're trying to be with somebody and they're blowing you off or maybe they don't want to really show up for you, you know? Not in a bad way, but maybe for clarity's sake, you know, maybe you don't need to worry about them because they're telling you. Got it, because you guys both had your Friends in San Francisco, so you were kind of doing solo stuff too, is that why you were kind of not connected at all times? Yeah, yeah, also her parents are in the Bay Area. So it just wasn't, it just wasn't lining up. I had this storybook like we would be doing these things together. You know, we both lived here. We could show each other things that we liked and what we were into in none of that happened. Were you two staying in the same room together? We were in a friend's apartment who was out of town so we were there and we did hang out together. We were trying to hang out trying to be together. We did have fun together, but it just something was off. It wasn't magic anymore. So what turned things around? Clearly, you're very doubt how did things move to a committed serious relationship? Yeah. So we left San Francisco and I was like, okay, this is going great. And she's like, no, it's not. Great at all. I was like, oh wow, okay. I'm really wrong. I could feel her continuing to pull away back her back in London to me in New York. And I just got very, very like, just my heart took over and was not pleased with what was going on. And it was basically like, she doesn't get it, you need to tell her in a really clear way that she can't misinterpret. 'cause I would say thanks to her like, hey, I really care about you and she'll be like, okay, I gotta go. And I would share what I was feeling and she just, she was closing. The door was closing. You know, that Indiana Jones moment, and I was like, I gotta go slide through that door and not lose my hat in the process. So this is also embarrassing. So I had to use Italian earlier and I also played the guitar. I had to write a song to reel her back in. I have really never done that before. I know that sounds impossible, but I've been playing the guitar for a long time. And this is the first time I wrote a love song for a girl. Wow. It came through me. I wrote lyrics that just I didn't even think about them. I was like, here's how I feel, and I recorded it, and I sent it to her. I didn't know what would happen and then at first she was like, what is this? And I don't really know or care, and then she listens to it again. And again, and again, and again, and then she realized that it was real that I really loved her. And that's what I was saying to her. Oh, so in the song, you profess your love to her. Not outright, but walked up to the door and was like, this is how I feel. Like we're supposed to, we're supposed to find out if this is if this is real love. Got it. Okay. So I've lost track of time Bloods a little, but this is probably like about a year later, right, from the trip. This is a lot. It feels like a lot of times past but. Yeah, we're closing in on a year, Julie. Thank you. So you're playing the log gave here both of you too. Yeah, that wasn't trying to, but yes, it's turned into the long game. And there's one more piece of this story. That's really important about where it seals, right? So that she's like, she gets it, she feels it. Her heart's opening up again. But we're still far apart. And one day she calls me on FaceTime from a beach in Mykonos. And she's like, hi, look at where I am. I'm like, wow, it's terrible outside and cold. Like, why are you doing this to me? And that her friend, who I had not met, this beautiful person named Hanukkah takes the phone and she goes, you need to get over here right now. I don't know what you're doing. But you need to you just need to be here.

01:00:04 - 01:05:02

And I was like, ha ha ha ha, that's ridiculous. And you put Amy back on or whatever. And Amy's like, oh, I'm so sorry, you know that Honda did the don't or do, I don't know. Don't do it. And but look, again, another invitation from the universe. This is something I would never do. Go to Mykonos for the weekend. That sounds beautiful. That sounds awesome. That sounds like what other people do. And like for me at the time, like, oh, that's what glamorous annoying people do. I'm not one of those people. But then I'm in the checkout line at Whole Foods, I'm like, let's just see how much the flights are. And I look and I'm like, oh, this one's actually pretty easy on the wallet and itineraries good. I was like, you know what? Screw it. I just love it. It's booked it right there. And I showed up in Mykonos. I gave myself a little bit of intention, which I'd never done before. I've heard on smart podcasts like this one to set intentions. And I was like, just have a ton of fun. Don't worry about anything else and just like live it to the max, like enjoy the shit out of this. And that's exactly what happened. We had a fucking ball. It was so fun and I got to tell her that I love her face to face and to this day, you know, we have a huge win in our sales from our friend Hannah, who helped us reconnect and unite and she helped marry us a couple of years later. Full circle. Wow. I feel like we need another whole episode to ask you how things actually went from this to marriage, but I guess if you could give us maybe like a very high synopsis, how did you go from still living close to each other to building a life together? Yeah, the short story is Amy quit her job and she moved to New York and she moved in to and I was like, just move in with me. And we'll figure this out really quickly. If it's going to work or not, and we're too, at the time, I think we were 35, 36. It's like we don't have a lot of time to waste if we want kids, which we do. So let's just hurry up. And I know that's crazy, but just move in and she did. And it basically has been working out beautifully. I believe. I love that. I mean, I'm going to go into some takeaways from this because this has just been such an incredible story, but one of the things that really stands out to be is that you did not follow any of the typical data timelines, right, of going out a few days. It's defining the relationship. X amount of time to move in and say, I love you. You kind of just played by your own rules with that. And I love how just organic this whole relationship was. So that's kind of just the first high level. But one of the things that stood out to me is just not overthinking the opener. You just said something. And we hear all the time of people that are just afraid to approach people in real life or even on apps, they're waiting for this perfect opening line. In the problem with that is that you're just not making moves and taking action. So even saying something that seems so basic or whatever, it's still better than saying nothing, it imagine if you didn't say anything. This entire life of yours would never have unfolded. So I think this whole piece that you said that this is a gift from the universe, if we can start to see all the interactions that we have with people out there as gifts from the universe and kind of have this mentality of why wouldn't you? You mentioned that a few times. I think that really stuck with me. It's like there's nothing to lose. The only thing to lose is not having this gift it receiving it. So the very last one I'll add was the power presence. You said multiple times that you were not overthinking the next steps of this. And what was going to go down? And I think that is something that a lot of us are really guilty of doing, especially when we're meeting on dating apps or somewhere that the context is am I going to date this person and get married to them versus a trip where you're kind of just like, ah, this sounds fun. Let me hang out with this person and see where it goes. So I think having this present attitude, even if you're not reading someone on a solo trip, but of course, opening yourself up on a solo trip too, it can go so far that you're just not overthinking every last thing or putting that pressure on until a natural connection forms. Yeah, I think that's so beautiful what you said. I totally totally agree with myself. Echoed back from your high level thoughts. You're like, you're so smart. I'm so smart. I surely did the right things, didn't I? I would, I would have changed how long it took if I could go back. It didn't, you know, I was overthinking too much, or just, you know, I had my quote plan and one thing I have learned since being with Amy is your heart knows all these things that your brain will figure out that it knew eventually.

01:05:03 - 01:10:04

You know, like it catches up to your heart and when I have listened to my heart or my gut is what told me to go to Italy in the first place to go and be able to meet her. When the heart and the gut tell you to do something, like you should really try to listen to that. Let that tell your brain, hey, that's why you're around because you're going to figure it out when we get there. And you'll make sure it's safe and fun and cool and that's what the brains could for. I love that. I think so many times we overthink and justify why something won't work, opposed to just doing it in making it work. And that at the end of the day is commitment is baking things work. Yeah. I think also with the opening lines, you know, I can, you know, I'm a stand up comedian. So I understand the need for a good opener, right? But I think you could just go in with like, hello, this is my opening line. I mean, if it's that or nothing, right? It's like, yeah. The reason why you didn't overthink it. So this is what the irony I find in your story is that you went all the way to Italy to meet a woman that you would probably met in the states somewhere, either in New York or in San Francisco or through friends or at freaking Burning Man that she goes to every year. So it's funny that people always think their city is to blame and you were in the middle of a transition of leaving San Francisco when it ultimately a false on our mindset. And I think your solo trip brought out this really courageous and playful and sort of curious side of you that sometimes is not our default behavior when we stay in our own cities. So what happened on the solo trip was that you're like, fuck it, I'm gonna go to the spa on my own. Fucking, I'm gonna wear this towel. Fuck it, I'm gonna talk to this girl. And you kind of throw those fears out of the way and throw the overthinking away too, 'cause you're on a trip in a foreign place. What do you have to lose? And I think we can really use that mentality in our home cities too, because we wake up and we have these knee jerk reactions to life, but if we can just change our scenery a little bit, maybe just move to a different room and stay in there for a few hours and see how you feel or walk around the neighborhood and take a different route, discover a new place, a new neighborhood. I think that really helps people to reignite that courage and that kind of playful side. I also love the fact that you two discovered each other. And it's an even kind of witnessing your relationship now, new discoveries are always coming up for you. And it all began with this trip and Copenhagen of I don't know anything about this person, so let's just try this. Do you like this? Or do you not like this? And I think that's what dating is about. You had no profile on her. You didn't know any background about her to judge her by. You just knew she was a cool girl that you connected with. You thought she was attractive, and you just wanted to get to know and discover more about her and that sort of what we're missing in modern dating is the discovery process because when we meet someone, we feel like we know everything about them already, which is not true. So I really admire that part of the story too. And that's why I think solo trips could really bring that out in people. Yeah, I'm a huge fan of being in reality to engage with people. For dating, I think. I have a bunch of friends who were doing the apps really hard. And I was like, well, the thing about that is going to be tricky. It's like you're a special unique marvelous person. And it's going to be hard for them to feel that on this profile. What photo or what words can encapsulate the magic of a human being? There are none. They'll never will be, in VR, it's never going to happen. Whatever they're cooking up over there is like it's always going to be less good than what it is. In the notion of solo travel doesn't have to be Europe. It doesn't have to be 6 weeks. It could be someplace in the neighborhood over from you that you've never been. Like some coffee shop and just go alone and don't be on your computer staring at it and or your phone and just be a little bit available. I want to just relay some info like that my mom told me and she is married and still married and they're about to have their 50th anniversary this year. She would get a ton of dates just going to the bar alone. She would just walk up to the bar and sit down and she always, she had three boys. So she can't relay this information to any daughter. So that's why I'm doing it right now because this is for her. Forward. Paying it for you, mom. If this is a direct quote, if you are halfway decent looking person, you can go to the bar alone as a lady and guys will be falling all over you. And you know what? I would love to see somebody try that because I think there's a lot of value in that kind of advice. It doesn't need to be a bar, but if you make yourself a little available in feel that discomfort and be like, okay. I'm just gonna, I'm just gonna be here. But I'm open, and I'm like, cool with it. I think a lot of amazing things can happen. Yeah, we had one of the moderators of our community do this all the time.

01:10:04 - 01:14:48

She's the queen of master data. And that's what we call it over here. And I think a lot of us justify to ourselves that no one meets in real life anymore. No one wants to, especially in COVID times. It's so difficult, but she had no problem meeting people wherever she went because she was putting herself out there in that situation, not in a gaggle of 50 girls either. It's just impossible for anyone to break through a group like that. So I think so many times. Again, it kind of goes back to this mentality of we can think about all the ways it won't work, but we could just do it and make it work, opposed to overthinking it also. Yeah. Yeah, I think if something's a little scary, then it's probably something worth drawing. Just a word of caution for anybody thinking about solo tripping this year. I would advise not to go on a solo trip thinking you're going to meet someone and don't have that expectation because what happens most of the time is you meet someone on your journey, not on your destination. And this is what happened to will. He was not going on this trip thinking he was going to meet his future wife. He was in it for an experience, thinking that he would find his future wife in Brooklyn, which was his destination. So I think setting the expectation, knowing that you're going on this trip purely to be curious and to explore the world, I think that will put you in a much more available mindset like will said. Yeah, I think that is exactly what's the problem with data gaps is that you're there to date, right? So it's very focused. So I think that advice could also even extend over to that world, right? I was here to meet another human being. Will said too, we keep echoing this, you're never going to know from a profile, but you will know when you actually meet that person and see if there's someone special. So great. Yeah, I think it's so cool being a little curious and saying hi and just having the ability to shoot this shit with somebody. If it just stops there, that's cool. That's practice. And you get your feet under you a little bit. I think that's a lost art a little bit, you know? Like when I get into an elevator, I'm like, cool, captive audience. They're stuck here. So what should we say? What would be fun? That's me, that's how I kind of like get some text, but I think that playfulness can be the idea that can be brought into this whole arena and change the outcomes for people. Like a comedian. Yeah, I was gonna say, well, being a stand up comedian and a writer, how much of the story have you used in your materials? Actually, none. So far. I know. I think that needs to change. Let's see how many downloads this podcast gets. And then if it's a lot, you know, we'll bring it into the routine. And if people want to learn more about the content you're putting out there, where can they find out more about you? Yeah, it's all at will rockland dot com. You can also follow me on Instagram at will Rocklin. So I'm very easy. Awesome. Well, thank you so much for joining us will. This was an incredible story. I hope it gave people a renewed sense of faith that you can meet people anywhere and the world is much smaller place that I think we think a lot of times. Yes, it really is. Thank you guys. Thanks for coming on our show, will, and for all of our listeners, hopefully this inspired you to do something out of the ordinary, push yourself outside your comfort zone, maybe go on at the solo trip or maybe just go somewhere solo for a few hours and see what that feels like, because you never know what can happen. And while you're on this solo trip, feel free to go into Apple podcasts and give us 5 stars and write a nice little reveal. Because you all have the time to do so and it looks like you're busy doing something and not awkwardly. Solo trip ever, right? All right, we're gonna wrap this up. The dateable podcast is part of the frolic podcast network. Find more podcasts you'll love at frolic media slash podcasts. Want to continue the conversation? First, follow us on Instagram, Facebook, and Twitter with a handle at dateable podcast. Tag us in any post with a hashtag stay dateable and trust us. We look at all those posts. Then head over to our website dateable podcast dot com. There you'll find all the episodes as well as articles, videos, and our coaching service with vetted industry experts. You can also find our premium Y series where we dissect, analyze, and offer solutions to some of the most common dating conundrums. We're also downloadable for free on Spotify, Apple podcasts, Google Play, overcast, stitcher radio, and other podcast platforms. Your feedback is valuable to us, so don't forget to leave us a review. And most importantly, remember to stay dateable.

Dateable Podcast
Yue Xu & Julie Krafchick

Is monogamy dead? Are we expecting too much of Tinder? Do Millennials even want to find love? Get all the answers and more with Dateable, an insider’s look into modern dating that the HuffPost calls one of the ‘Top 10 podcasts about love and sex’. Listen in as Yue Xu and Julie Krafchick talk with real daters about everything from sex parties to sex droughts, date fails to diaper fetishes, and first moves to first loves. Whether you’re looking to DTR or DTF, you’ll have moments of “OMG-that-also-happened-to-me” to “I-never-thought-of-it-that-way-before.” Tune in every Wednesday to challenge the way you date in this crazy Dateable world.