Cadiz Pirates: On Dating After Long-Term Travel

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.”