On Dating After Long-Term Travel

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As he strolls up to me in the park, I’m relieved — he looks just like his picture and he’s wearing a nice outfit. I admire the whimsical navy-on-pale-blue paisley shirt, the slim dark pants, the warm leather shoes. He leans in for a brief, gentle hug.

It’s the most innocuous of first dates in Manhattan — a walk in the park followed by a coffee. No mind-altering substances, no major financial investment, and easy to escape if it comes to that.

After a stroll on this gorgeous spring day, we sit down at a cafe. We’ve gone through the pleasantries and talked about where we grew up, our families, the train wreck that is the 2016 election. Nothing about jobs, or how we spend our time, but that’s about to change.

“It’s so cool that you’re a digital nomad!” he exclaims.

I pause. I don’t tell anyone what I do for a living until the third date at least — the best option when a quick Google search could lead you to MY ENTIRE LIFE SINCE 2010. “What makes you think I’m a digital nomad?”

“I searched for ‘digital nomad’ on the site and your profile popped up!”

And then it hits me — under the “What am I doing on a Friday night?” tab, I put a list of wacky, whimsical activities in New York. Cocktails with friends. Coming up with new, awful phrases for Cards Against Humanity. Karaoke in Koreatown. The odd warehouse party in Brooklyn. And yes, some quiet nights on the couch with Netflix.

(Let’s be honest, though — on Friday nights I’m far more likely to be cleaning my apartment while listening to podcasts.)

And then I remember that I had listed digital nomad networking events on there as well. Why had I even written that in the first place? Most of my work-ish events revolve around entrepreneurship more than remote work. (Okay, let’s be honest again — most of my work-ish events are getting together with other travel bloggers, drinking copious amounts of wine, and gossiping.)

So that’s how he found me.

“I think it would be amazing to live in Thailand for a year,” he says.

I nod with a smile. Here we go. The travel conversation. Where I must strike the balance between being knowledgeable and not a know-it-all, experienced but not emasculating. The struggles that every straight woman faces when out on a first date. “Thailand is great. One of my favorite countries.”

“I haven’t been, but I want to go so bad!”

“You’ll love it,” I reassure him.

“Just — all that food. I hear that Thai food is so much better in Thailand than here. It’s so different. And it’s so cheap!”

“True. You can get a great meal for two bucks. Or even less.”

“So when you were traveling for five years, did you ever live in Thailand?”

“No. There was one point when I wanted to.” Large swaths of 2011, mostly. “It’s good temporarily, but ultimately, the bad outweighs the good for me.”

“How could you not want to live there?” he asks. “Thailand has everything!”

“Well, nobody ever talks about the downsides.”

“Like being so far away? I could live with that.”

“Yeah, that’s one thing. And it’s annoying being in the opposite time zone all the time.” I pause. “Do you really want to know about the bad stuff?”

“Yeah. Tell me.”

“It’s hard living in a culture that’s not your own, particularly when you don’t speak the language and especially when you’re in an Asian culture. The expat communities are great, but people are always arriving and leaving, and it’s hard when you’re constantly saying goodbye to your friends.

“And most people end up in Chiang Mai,” I continue, “because it’s the cheapest spot in Thailand that also has Western amenities and decent internet. And it’s a great city, but a lot of people think they’ll be on the beach and it’s a long way from the beach. Two hours of flying if you’ve got the cash, much longer by train or bus. Great food in Chiang Mai, though. Oh, just know that Thai food is full of sugar. Fruit shakes, too.

“And there’s this idea that Chiang Mai is full of brilliant entrepreneurs, and there are a few of them, but for the most part it’s full of people who can’t afford to live anywhere else. So you think you’ll be doing this amazing networking, only most people haven’t figured out how to make much money yet.”

His face falls.

“I mean, you never know,” I say, quickly backtracking. “I never rule out anything. I could go live in Chiang Mai for a few months if I wanted to reduce my living expenses and funnel all of my money into the business. And I’d still get foot massages every day. Seven bucks an hour.”

“What if I lived by the beaches instead?”

“They’re good. The really beautiful ones are remote, though. And it’s much more expensive there.”

“Cheaper than here, though.”

“Yes. Much cheaper than here.”

“And just imagine the quality of life — you can run on the beach every morning, you can work on the sand and watch the sunset every night.”

“Careful with that!” I laugh. “That’s one of the biggest myths — no one actually works on the beach. You don’t want sand in your laptop.”

“And I hear Thai people are so nice! Just, you know, the kind of people that would give you the shirt off their back. It must be the Buddhist thing. People are calm and happy.”

I smile tightly. “Yeah. I like Thai people a lot.” Though the words of a Singaporean bartender in Koh Lanta echo in my head: “You nice to Thai people, they’re nice to you three times. You FUCK with Thai people, they FUCK you three times!”

My date shifts in his seat and sighs. “Well, I can’t go to Thailand yet, anyway. I need to stay in this time zone for my job.”

“Oh. So you’re a remote worker?”

“I can work from anywhere as long as I can be on their schedule.”

“Ah. That’s cool.”

“Have you been to Medellín? I hear it’s so great there.”

“No, not yet.” (Though I would a few months later.)

“I hear it’s the most beautiful place in Colombia,” he tells me. “Just — it’s supposed to be a beautiful city.”

“Mmhmm,” I reply, biting my tongue. When most men talk about the beauty of Medellín, it’s not the city they’re talking about.

“There’s just one thing,” he says. “Why do you live in New York when you could live somewhere so much cheaper?”

I’m ready for this question. “Why would I live anywhere else if I could live in New York?” I say, tilting my head with a smile.

“Yeah, but you get so much more for your money everywhere else!”

“I don’t know,” I tell him. “I think I get a lot more here. My friends. The culture. Networking. A major flight hub. I’m just a bus ride away from my parents. Everything happens here.”

“You have a bigger chance of being shot to death in New York.”

“That is true.”

“And the healthcare system is so bad.”

“Agreed, it’s awful. I couldn’t come back if it weren’t for Obamacare.”

“So what makes New York so much better?”

“New York is everything and everything is New York.” The words tumble out of me; I’m surprised at how much I like them. “I’m never going to be bored in this city. There’s always something new to discover. And lately I’ve been feeling an urge to work to make my country better.”

“I don’t know. I just think Thailand is a much better place to live.”

“Well, maybe for you,” I offer. “At any rate, I spent five years traveling the world and I chose to settle down here. Plus, there are crazy milkshakes in New York. And 90s parties. And tacos.”

He lights up. “A lot of people go to Mexico! I hear Playa del Carmen is the place to be. It’s so cheap and it has a great expat community. And so much good Mexican food.”

I smile.

“What’s wrong with Playa del Carmen?”

“Oh, nothing — I just have a ton of friends there.”

“Digital nomad friends?”

Why does this phrase always make me cringe? “Yeah. They work online.”

This guy is nice. A little mansplainey for my taste, but this first date is far from the worst.

Dating is weird in the world after long-term travel. Mention your travels in an online dating profile and you’ll attract a lot of people who would love to travel but haven’t yet and see you as the catalyst. Mention your desire to settle down and you’ll attract a lot of people who aren’t into travel at all. “I’ve traveled a lot but I’m content being more settled here” isn’t exactly a category.

I’m grateful to live in New York, though, home to many driven, entrepreneurial, creative people, even if they’re always searching for something better. If my suburban friends’ OkCupid matches are any indication, things are far worse in sparsely populated areas.

It just goes to show that sharing common interests isn’t enough — you also need to be on the same timeline. It’s not enough to enjoy travel to the same kinds of countries, or to be able to work from anywhere. One person wanting to live abroad and the other being content in New York is a fairly big dealbreaker.

“So.” He plays with his empty coffee cup. “I don’t know if you have somewhere to be, but do you want to get a drink?”

I’m certain that this guy isn’t a match. A drink won’t change that. We’ll loosen up, we’ll tell more stories, we’ll say goodbye for the evening, and if he wants to go out again, I’ll let him know kindly that I had fun hanging out but I don’t think we’re a romantic match.

But it’s not like I have anything to do. I’ve already cleaned my apartment and listened to my podcasts.

“Sure,” I say. “Let’s get a drink.”

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57 thoughts on “On Dating After Long-Term Travel”

  1. Oh dear, the struggle of meeting guys that want to go abroad while oneself is ready to commit to a place for more than just a few weeks is real!

  2. Timeline and interest in traveling are so important.

    I remember being in DC trying to date but meeting so many guys who ‘liked travel’ but had never left the country because they were too busy trying to get ahead in their career.
    Meanwhile, when I met my (current) boyfriend, I liked that he had already done a lot of travel, but was open to traveling more, living abroad, AND was focused on having a family eventually.

    Just know that the right person is out there – you definitely DO have better odds in NYC than somewhere more quiet or isolated.

    1. Oh yes – same in Chicago. Everybody “likes to travel”, but they never really do because of their careers. It’s boring!

  3. oh my. cringe so hard at reading this post.

    consider dating an older gentleman who has done all the traveling and now looking to settle down, maybe? or an expat who considers NYC his ‘living abroad’ situation…

    also the realities of living as an expat in thailand.. ouch!

  4. Totally feel you on this one. I’m just getting back from living abroad for 4 years, and I haven’t dipped my toes in yet but wonder what it will be like once I do. I agree with needing to be on the same timeline. If the other person is still in fantasizing phase, it’s hard to not want to burst their bubble. Plus, if they are around my age and haven’t done something they say they really want to do, I find that a little bit of a turnoff. If they really wanted to do it, they would find some way to do it. It’s a sign that they may be all talk.

  5. This is a very well written post! I’m an Indian guy who’s travelling in India and it’s even harder here; most people don’t understand long term travel yet, and the ones that do are far crazier than me.

    Just run-of-the-mill normal people who travel, a category that doesn’t have many representatives 🙂

  6. “Where I must strike the balance between being knowledgeable and not a know-it-all, experienced but not emasculating. The struggles that every straight woman faces when out on a first date.”
    Thank you for putting words on why I hate dating, you killed me with this one 😉
    Why can’t we just say what we think/know, for sweet tofu’s sake?

  7. Another thing I’ve noticed (that I hate) is that many guys see travel as a couples only activity. You’ll see on dating sites “I’ve always wanted to go to X place but I’m waiting for that special someone to see it with..” and the only travel they’ve done is with ex-wives or ex-girlfriends. That bothers me probably more than it should.

  8. I feel you, completely. My timeline is showing a move abroad for 2018 and meeting people now, here, just isn’t running on the same timeline. It makes it impossible when they think of travelling or living abroad as only a pipe dream or something too crazy for themselves. Leaves me wanting…

  9. Oh my goodness, this. It’s so incredibly important to be on the same timeline as someone. There are a few people in my life that I could have seen myself with but the fact that we were just at different stages in life and wanted different things at that moment in time made it impossible. Finding that person that you like, have things in common with and that you’re also on the same page with takes time. Dating in 2017 is HARD!

  10. Hey Kate, I just wanted to commend you for how much your writing has improved over the last few years. Don’t get me wrong — it was never bad! I’ve always really enjoyed your style. But I feel like all these book challenges are helping you immensely. I’m on book 3 of Elena Ferrante’s Neapolitan Series per your suggestion, and your writing is definitely very reminiscent of hers in this post! Really well done and a joy to read!

    1. Kara, that is such a kind compliment — so nice of you to say that. Elena Ferrante is one of my favorite authors. Thank you so much!

      And it’s true — you can’t be a writer without being a reader.

  11. LOL. I hate that too! I hate even talking about it with people I don’t know like at regular networking events or when I meet my boyfriend’s friends/coworkers or a friend’s friends. I just downplay it a lot and ask them a million questions about themselves.

    Good luck dating in NYC though. Your blog posts should consist more of that from now on! It’d be hilarious (kinda like Jen Glantz).

  12. Kate I find it so unbelievable that guys aren’t lined up at your door. In a city like NYC if you can’t find a fella what is the world coming to!
    You will find one though & he will tick all the boxes & no doubt he’ll be just around the corner. He’ll be one lucky guy too, hang in there.
    PS I tots understand why you live in NYC because you can. If I could I would but Melbourne is where I lay my hat. I’m visiting NYC for NYE this year with my tribe of 5 & im so excited it keeps me awake some nights thinking about it!!!

  13. Ooof this stresses me out. Such different timelines. Bless him, he’s probably perfectly sweet and everything, but it’s tough when you have very different experiences like that, or really, are on opposite ends of the timeline spectrum.

    I think NYC would be an amazing place to live. Always so much happening. And we don’t always make choices based on where we can “get the most for our dollar” and you’re fortunate that you don’t have to do that, anyway! It struck me what you said about Chiang Mai. We didn’t end up going there (I’ve still never been to Thailand) but I think that’s so true about people ending up there because they end up unable to afford anywhere else. That’s a problem with the digital nomad lifestyle and why we decidied to stop traveling and stay in the USA for a while to make money and truly build up our businesses.

    Anyway., brilliant post with engaging writing, as always. You’re a great storyteller!

  14. I haven’t traveled nearly as extensively as you, but I lived in Paris for a year (not as a study abroad through college, but three years after graduation, as an adult). It was the most exciting thing that ever happened to me. When I got back to Chicago, I met a guy at a young adult Shabbat dinner at a local synagogue. We went out for dinner, and I started a story with “When I lived in Paris,” and he was like, “Ooh la la, so you lived in Paris?” But not in a good, curious way, in a kind of derisive sneering way, as though he thought I considered living in the States or in Chicago somehow beneath me. It kind of made me wary to tell people that I had lived in France, even though (as you say about Thailand) there were plenty of challenges and negative aspects of my year there.

    Also, re: putting what you do for a living in your dating profile, I’m an opera singer. Good luck with THAT one. 😉

  15. I write about romance and travel, yet I haven’t really had more than a handful of dates in the past 5 years! You’ve pretty much described why in this piece. Often when men ask what I do and we discuss travel they say things like, “Oh, so your ideal partner would have to be pretty rich to keep up with you, jet-setting around the world,” (wrong!) or think I’m too busy traveling to have a real relationship (kinda’ true). So, I write about romance & travel while on a cruise- with my sister. Thanks so much for being such a kick-ass blogger, but especially for your desire to try to change shit going on in our country rather than to take the easy route and leave.

  16. Does striking “the balance between being knowledgeable and not a know-it-all, experienced but not emasculating” only apply to the travel conversation when it comes to dating these days? Sometimes I hate how early in life I met my husband, but when I read these pieces on dating from my favorite single female bloggers, I feel relief. And not in a condescending sort of way (it’s dumb to be smug about luck), but because I don’t remember having to worry about this in my 20’s. In fact, I think the rebellious Winona Ryder-esque heroine type was still prominent in the late 90’s/early 2000’s, so I don’t know… maybe giving off the vibe that you were intelligent didn’t translate to emasculating? Add to that the pressure of social media and conversing primarily through texts (don’t even get me started), and you have it WAY harder than women did just 15-20 years ago.

    I know it’s easy for me to say, but try not to think about that so much next time you’re on a date. You are a woman who’s created her dream career based on travel experience and expertise — do you really want to be with someone who would make you feel like you have to reign that part of yourself in? That makes no sense. The right man for you will feel empowered by your strength. He’ll also have plenty of his own. Diluting that part of yourself early on will only delay the discovery of whether he’s into the real you or not, and what’s the point of that? I’m not saying be a cocky asshole (who likes those?), but you shouldn’t temper the knowledge on which you’ve built your impressive profession at the risk of scaring someone off. If that’s all it takes, he’s not for you anyway.

    1. You know, I’m glad you acknowledge that it’s been awhile since you’ve been in the dating scene, but I don’t think this is a recent development. Women have always had to keep their personalities in check to not offend their male dates, coworkers, family members, etc.

      And it’s easy to say that the right guy will love you exactly the way you are, but there’s a fine line between appearing knowledgeable and appearing to be a snob. And coming off negatively can make the difference between progressing to a second date or not, even if you happen to be a good fit for each other. A lot of people are more innocuous and inoffensive on a first date and drop their guard afterward.

      1. I get what you’re saying. I do. That’s why I said “I’m not saying be a cocky asshole.” I might’ve just picked up inaccurately that you felt like you couldn’t appear knowledgeable about your profession (not just holding back personality-wise), which I think is a common fear many women have, but why? Even in non-dating circumstances, like when I’m at a military function usually surrounded by often conservative and opinionated men, I end up finding that many find it admirable that I’m not afraid to speak my mind — and I’ve often had some very interesting (respectful) arguments and conversations come out of it. Like you said, I’m not going to go in there acting conceited or condescending, but no one likes those traits in men, either. (Or at least I don’t.) I agree that we’re often made to feel we’re not “supposed” to come across as having particularly strong personalities, but I think sometimes we do it to each other or even ourselves.

        And I’m definitely NOT saying the right guy will love you exactly the way you are. The right guy will respect your intelligence, your strength, and challenge you in other ways, maybe even ask you to see the world a little differently. Every relationship involves compromise and the understanding that you’re two different people. And of course you don’t want to be offensive on a first date — but should you ever want to be offensive? What I’m saying is, though, wouldn’t you rather be with someone who isn’t automatically emasculated (or offended) by you imparting knowledge you’ve learned over years of evolving this profession when he’s actually asking you about it?

        I do get what you’re saying that you don’t want it to be overkill and that it can be scary when the question comes up because you’re wondering how he’ll handle it. I never dated in New York, either — it was the midwest and, despite what outside impressions might be of the place, I never grew up feeling I had to be “less-than” as a woman. (It wasn’t until I moved to the south that I really felt that pressure.) So maybe that translated to the way I dated? And also probably why I never had a long-term relationship prior to the one that stuck. Ha!

  17. I love this post! Creative. And I feel the same way. I just moved to NYC after spending most of last year abroad. I am not looking to date people but I can understand the importance of timing and being on the same page.

  18. Oddly enough, from a male point of view, I hated dating (this was decades ago). It was not the real world. I reckoned if I was doing something and wanted to include a girl, then fine – or vice versa (she was doing something regular and I could fit in). Normal things are the everyday stuff we do and if a date didn’t fit into everyday life, then a date is, in a way, irrelevant. Dates happened after meeting and became something special. If the “special” becomes the only time you meet up then in everyday life the relationship would probably disintegrate very quickly.

    1. You make a great point! I often think of this when I catch a bit of dating TV shows that my mom watches. It’s also why I would want to live with a person first before I even think about marriage, etc.

  19. A bit mansplaining? You have a higher tolerance than me! haha

    I’m struggling with a similar thing being on tinder after being away for 15 months. People either only want to talk about my travels, or they feel like they can’t relate to me because I’ve been on this trip and its not something they are hugely interested in doing. I’ve given up a little!

    1. I am in the same situation now, and I haven’t really touched Tinder yet. I reinstalled it and updated it so it says I’m in NY, and replied once to a message, but really I have no energy to go through the whole Tinder dance!

  20. What an interesting peak into your dating life. I never thought about being well travelled as an issue, but I guess it does put you in a weird postion. Thanks for sharing! Your post kept me very entetained.

  21. First of all, let us tell you that your writing style is really captivating and interesting, this is one great article you have introduced to us, girl! Somehow shared experience, or as you say it, being on the same timeline is really, really important. For someone that have already lived abroad and experienced all the downfalls of this it would be a lot easier to understand you. The glamorized image of life abroad with all the adventures and getting out of your comfort zone is not necessarily a good thing.

  22. Oh wow!

    Loved this. As a traveler..totally get you towards the end..you and the mansplainer are at different places. He’d love to begin travel…you’re kinda travel-weary at this point and just want to kick back and relax, see and enjoy your city with the ‘freshly-peeled-eyes’ of one who’s been constantly traveling.
    It’s like Maslow’s hierarchy of needs..he doesn’t quite fit the bill.

  23. Kate– I’ve basically lived out everything written in this post. After being transient for 11 years, I’m beginning to place some roots and travel less frequently for many of the same reasons you’ve expressed in this blog. Thank you, thank you for putting my feelings and thoughts into words. I needed this. Can we create a dating app for people like us?

  24. Love this story and how you told it! There is so much recognition. Not only about dating, but about meeting people in general. Some people are nice to me, but the moment they hear I work as ‘a digital nomad’ they wanna know and hear everything about me. It sometimes makes me wander if they would like me as a person as well if I wasn’t living like this. I downloaded Tinder a couple of weeks ago but I kind of regret that now. THe moment people started to ask questions about traveling and living on the road I felt like a searching machine.. There was even a guy who send me a message on Instagram because he saw my profile on Tinder and found me with some mysterious help… ;o Dating must be quite weird after traveling so long, right?

  25. I can totally relate to this post. I travelled through 24 countries last year and I ve met many guys, but they usually didnt last, because I only spent one or two weeks in each country. So I know how lonely it can be for travellers.

  26. This is a really interesting post. I really enjoyed reading it. You mentioned networking a few times in the article. Do you have any advice regarding professional networking while traveling?

    Random question: what plugin do you use for your social media sharing?

    Best of luck!

  27. Hey Kate,
    Thanks for this post. Quite interesting. My wife and I went on a 16 month trip and had conversations like this. Though these days we find the people we want to just be around aren’t the ones that are constantly talking about travel. It’s great as a common denominator but if they haven’t gone out and have this fantasy idea of what it means (which may be completely off compared to your own ideas) then it gets a bit annoying. Thanks for your thoughts and good luck on the scene!

  28. People will have their own interests you dont need material things or hobbies to have stuff in common

    Plus obamacare serious?? Healthcare in asia is far better my family in usa have seen premiums shoot up and service go down comsiderably since obama care. Hopefully trump can sort the mess out

    1. Prior to Obamacare, I could not get health insurance in the United States because I have a preexisting condition.

      You know many people in the same boat as me, Jay. Don’t forget that.

  29. Best line in this great post: “strike the balance between being knowledgeable and not a know-it-all, experienced but not emasculating”. The struggle is real.

  30. I tried dating a little while I was working in upstate New York firstly with a guy actually from ym home town so massive coincidence we both ended up there but even then the pressure of us both knowing we would be moving on soon plus us both having someone we where seeing before we left that may be a possibility didn’t help, the thing I found as well is that as a foreigner in a country you’re almost a novelty like boys get intrigued by the accent and the different life you have and vice versa of course but you never end up having that connection.

  31. Compared to most of the people here, I am amateur when it comes to travel (mostly week-long trips in the US, for which I save for months at a time) and I STILL get guys who approach me and think I’m this magical creature they’ve been waiting for who will sweep them off their feet and guide them in fantastic adventures all over the globe. The truth is, if you are not willing to take the plunge yourself I have no desire to be your catalyst, and I’ll in fact find you boring AF.

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