Why I’ll Always Ditch My Boyfriend to Vacation with an Ex

Illustration by Vivian Shih

An adventurous man is hard to find.

Despite the dim lighting, it’s obvious the man undressing in front of me won the genetic lottery. His 6’2” frame barely fits in the double bed we’re sharing in a Bucharest hotel. There’s no hiding the fact that he has a chiseled, square jaw—even if it’s buried beneath three days’ worth of stubble. The only downside to his long blonde locks is that they partially obscure his sparkling blue eyes. Stripped down to boxers, he slides in next to me, where I’m half-naked, too. After all, like most cheap hotels in Europe, ours lacks AC.

Dylan and I are both straight, sexy, and single. But neither of us is getting lucky tonight. We have to get up early for a tour of Transylvania. Plus, we’re exes. We’ve been there and done that. It didn’t work.

About a year before Bucharest, and after five years of dating, we separated. It was a mutual decision. Dylan moved to North Carolina to get his MBA. And instead of following him, I downloaded Hinge and hopped on a plane to Portugal. But I never deleted Dylan’s number. While I had to cross him off my list of potential life partners, there was no way I was crossing him off my list of travel partners.

In my opinion, finding someone you can travel well with is harder than finding a mistake fare. Just because you get along with someone—i.e. your bestie or your brother—at home, doesn’t mean you can take that show on the road. Travel soulmates are the needles in proverbial haystacks, and that’s why if I find one, I never let him out of my sight.

While I don’t have a type, per se, most of my exes from serious relationships have one thing in common: They don’t just survive in foreign environments, they thrive. Like me, they have flexible schedules, ample disposable income, and a desire to see the world. That’s why we were attracted to each other in the first place. So, even after we break up, we keep traveling together. It’s a mutually beneficial experience we’re not willing to throw out with the bathwater.

Michael Sawyer, who’s operations director at the guide company Ultimate Kilimanjaro, said the best travel partners he’s seen were a couple who had called it quits but still wanted to conquer Africa’s tallest mountain together. “The trip went smoothly since they respected each other and knew each other’s travel habits,” he recalled. “They were able to concentrate on the road ahead instead of their differences. If you approach traveling with an ex from the right angle, it can be an amazing experience.”

I agree. Take, for instance, my aforementioned relationship with Dylan. He and I have traveled more together after breaking up than we did while we were dating. Our first post-breakup trip was a 10-day luxury Mediterranean cruise. At the time, the electrician I was casually seeing couldn’t get the time off. And all my other friends were getting married or having kids. Meanwhile Dylan had vacation days and thousands of dollars burning holes in his boardshorts.

We laughed it off when a group of tourists sent us a bottle of champagne in Capri, thinking we’d just gotten engaged. And we didn’t argue when I decided to hang back in Genoa while he went to see the tower of Pisa—a lame tourist trap. If we’d been dating, doing our own thing for the day would have been a dealbreaker. Instead, for the most part, we operated like a well-oiled machine: I researched activities, he researched restaurants. The best part was that we didn’t need to feel self-conscious about our shortcomings or feel a need to impress.

We’ve also spent a week together in Rome, one of the world’s most romantic cities. I played tour guide because I’d studied abroad there, and he played Daddy Warbucks since he made six figures. Later, when I asked if anyone wanted to go to Romania, it was Dylan who raised his hand the highest—we’re both fascinated by the former Eastern Bloc. Then there was the trip to Thailand, where I picked up multiple parasites. Dylan wasn’t grossed out by my explosive diarrhea, but the Aussie cyclist I was talking to at the time probably would have been.

Dr. Deb Castaldo, a couples therapist and author of The Relationship Reboot told me the tide is changing when it comes to how we view past relationships.“While connection to exes has traditionally been seen as destructive, a new idea is currently coming to the fore: keeping connections to past loves can be very healing and fulfilling,” she said. But setting boundaries is important, especially if you’re traveling with an ex and you have a new partner. She advised making sure to discuss why you’re traveling with your ex with your current partner and giving space to whatever feelings arise. “If your current partner finds your connection hurtful or unacceptable, respect their wishes,” she added.

Dylan admits that he initially had reservations about me traveling with exes when he and I were together. “It was strange,” he said recently. “But I figured you wouldn’t be telling about it if you were just out there fooling around with them.” He recalled trying to keep an open mind while also remaining cautious about his hopes for our future together.

Little did he know that he’d eventually be the ex I was traveling with.

Of course, Dylan isn’t the only example. There’s also Firefighter Matt, a taller Jason Statham look-alike. We dated for a few months before deciding—while traveling in Costa Rica—that we made better friends than lovers. Later that year he met me in Portugal for a week of surfing, cycling, and flirting. But not with each other. I was chasing Portuguese guys; he was chatting up Canadian girls. Mature adults who respect each other, we knew better than to bring the people we were “talking to” back to our shared hotel room. Then last summer, he was my plus one in Jackson Hole, where we dined on Japanese wagyu at the Four Seasons and lost our Via Ferrata virginity on the mountain. Firefighter Matt is the perfect travel partner because he gets so much vacation time. Plus, he doesn’t have a partner, pet, or kids.

Then there’s Lian. Imagine Matthew McConaughey, but with a South African accent, and you have my favorite former flame. We met on Tinder in Thailand, fell in love (at least I did) on a Disney Cruise in the Caribbean, and went our separate ways in Florida after I played the ultimatum game. (Spoiler alert: I lost.) That said, we’ve stayed in touch and meet up whenever work brings me to Cape Town. Usually, we go to wine country. In May, we stayed at La Residence, a five-star boutique hotel in Franschhoek, where we slept in what’s rumored to be Elton John’s preferred suite. Lian and I travel well together because we have similar hobbies: reading, hiking, and cycling. Currently, I’m trying to talk him into joining me in Tanzania for the inaugural Wagora MTB Ride.

It turns out that I’m not alone. In fact, Katherine Alex Beaven, a travel journalist I met in Peru, has been traveling with her exes for a whopping two decades. Her first time was with Jeremy, a musician she dated in her 20s. Not long after breaking up, they decided to spend a month on Warped Tour. “We were living out of a van,” she recalled. Did the close quarters lead to someone snapping and committing second-degree murder? Nope. “When you’ve dated someone it’s easier to speak up when they do something annoying,” Beaven told me. “The communication level is there and there have been a lot worse fights.”

Like me, Beaven appreciates being able to voice things that you wouldn’t feel comfortable saying in front of friends or new partners. You have less to lose with your ex because, in a way, you’ve already lost. Plus, you’ve already proven to be compatible. “I think it’s strange to not be friends with your exes because there’s a reason you were together in the first place,” Alex said. She even introduced her next boyfriend, Mischa, to Jeremy. They hit it off and it wasn’t long before all three were traveling together.

Despite eventually ending things after six-ish years of dating Mischa, Beaven called him when she was planning a cross-country roadtrip during the pandemic. “He had been my default person to travel with for more than half a decade, so he was my go-to.” He didn’t hesitate to join her. Since then, they’ve traveled everywhere from Jamaica to Sri Lanka.

Of course, every trip with an ex begets the same tired question from friends and family: Did you guys hook up? They’re flabbergasted by our ability to share beds with our former partners without sharing our bodies, too. Some however, are inspired. “I’ve had friends try to be friends with their exes after seeing how good my relationships are with mine,” explained Beaven. “That said, it doesn’t always work.”