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Jun 10, 2016 

When I first told my friends that I was spending the weekend in a Mexican mansion on a date with a stranger, they thought I was insane.

"Diana, this sounds a lot like prostitution," they said with raised eyebrows and concerned stares.

Indeed it did, and that's precisely what I thought when I first came across Miss Travel, an online travel dating site founded in 2012 by Brandon Wade, the same man behind the sugar baby/sugar daddy website Miss Travel functions like any other dating site, in that users create profiles and message back and forth before arranging to meet if they hit it off—but rather than having your first date at a local dive bar, you have it at an all-inclusive resort in Bora Bora.

In theory, it's a site for people with a disposable income who love to travel and want to add a date into the mix. Miss Travel gives you the option to offer a free trip to someone or find someone to pay for your trip (though there are a number of lonely souls offering to go halfsies, so it does, to some degree, serve people who might just want to go somewhere with another corporeal form).

But, of course, the subtext is sex. Just…sex somewhere other than your place. And maybe sex because someone else paid to whisk you away.


Surprisingly or not, the bulk of the clientele is women—the breakdown, according to Miss Travel, is 70% female and 30% male. (This might be intentional, as the brand splashes "females are FREE!" across its membership materials.)

Go to the site and you'll find a community of brashly straightforward people, with every profile very clearly defining precisely what the person wants. You'll find men looking for relationships, wanting to "have fun and see where things go," or being openly honest about the fact that they're married and busy and just want to "introduce someone to the finer things in life" in exchange for some side action.

The women are equally blunt, if not more so—and most of them seem to be seeking funding for the trips of their dreams, fully aware that there's an expectation as a result. Many profiles specify precisely where they want to go and what they are or aren't willing to do when they get there. Some want added perks, like a shopping fee, on top of the free trip.

The romantic in me hates the idea of diluting a relationship into a business transaction, even though I'm not too much of a pollyanna to realize that all relationships are, in some way or another, a type of exchange. But the part of me that's allergic to bullshit really admires how no-nonsense the site is, especially compared to the illusory ideals of Tinder, where the same men who feed you a feast of feminist terminology turn around and freak out when you don't want to sleep with them after your first date. In this way, there's something respectful about the candidness of Miss Travel; the act of saying "This is who I am and this is what I want," free of judgment from society at large.

Choosing My Date

I'd been ruminating on it for months when an email serendipitously appeared in my work inbox one morning from the publicity department of Miss Travel asking me if I was interested in going on a trip with someone from the site to understand the "travel dating experience." The deal was that Miss Travel would select some candidates for me who were active on the site, and once I picked one, we would fly both of us out to some exotic location for a long weekend. Reporting + a weekend getaway? I agreed.

The PR contact responded with five candidates who were interested in going away with me—all of them were attractive, in my desired age range (27-35), and had impressive résumés. I weighed my options and decided it was between two guys: one who was in finance and lived in New York and was grade-A gorgeous, and another who owned a tech business in San Jose, and—while maybe not *as* attractive as the other guy—was someone I had a lot in common with.


The site recommends that everyone Skype their potential date before they travel. I went a step further—and broke the rules a bit—to meet up with D, the finance guy, in person. He automatically had a strike against him because he made me schlep to a hotel bar even though I'd hinted it was inconvenient for me (and was, fun fact, a block away from his apartment). "This isn't Seamless for Women," I was prepared to say when I arrived.

But when I got there I ended up not having to, because he was extremely nice and normal. Our conversation flowed naturally, like a great first date. I was starting to think this was my dude. Then I made the mistake of asking if he'd ever been in love."

No, I don't think so," he said after a long pause that told me he definitely had not.

"Okay, well have you been in any serious relationships?" I asked.

"Nah," he trailed. "I don't have the time, honestly."

"So, are you like a love 'em and leave 'em type?" I asked.

"I've actually never had a one-night stand," he said plainly.

I nearly choked on my mimosa. Why does this person even get up in the morning? And why the hell is he offering to take girls on all-expense-paid vacations if he isn't going to hook up with them?

"Okay, so if you don't don't do one-night stands and you're not looking for a relationship or true love, then why are you on the site?" I asked.

"Look, when I first got to New York, I didn't even go out. All I did was go to the office and the gym," he responded, describing my own personal version of hell. "I get a kick out of traveling and it's more fun to go with a girl, and it's no big deal for me to drop some money to do that. But I'm busy so I don't have time to get to know someone. This simplifies things."

In the weeks that followed, I would interview a lot of men and women who use the site, and the line "I'm busy so I don't have time to get to know someone" came up over and over again.


"Do you ever worry that you won't ever find someone?" I asked D.

"Nah," he said. "I'm sure one day I'll just grow into it."

In the spirit of getting what you want out of the exchange, I got up, gave him a kiss on the cheek, and said goodbye—as much as I'm here to report on the experience of travel dating, I might as well do it with someone I might see again afterwards.

The next day, I Skyped the guy I would end up choosing to go with. I'll refer to him as E. E and I had a lot in common—we both speak the same three languages. Our families are both immigrants. He went to Harvard, I went to Oxford. Bottom line, I felt that we could at least pleasantly spend a weekend together in paradise. And he made sure to tell me that he was actually moving to New York in May, thereby implying there was some long-term potential there if we happened to hit it off.

Three w