It’s been my experience that the less prepared I am to hook-up, the more likely it is to happen. On Christmas Day, 1999, I was camping on a Southeast Asian beach, when I came down with the flu, combined with bronchitis. I somehow managed to find the last vacant room on the island — a cell-like bungalow that mercifully had a Western toilet. I spent the next week riding out a high fever accompanied by a truly disgusting cough. Fortunately, a large group of Aussie friends were occupying the adjacent bungalows. In between drinking copious amounts of beer, they took care of me, bringing me water, Gatorade, and medicine. Even in my sweaty, phlegmy, semi-delirious state, I noted that one of them — a devastatingly handsome, sweet-natured guy I’ll call H — seemed to be dropping by more frequently than the others.
When my fever finally broke on New Year’s Eve, I joined the Aussies in celebrating the millennium. I was haggard, weak, and stone cold sober due to the antibiotics I was on. H spent much of the evening by my side, and I was shocked when he kissed me in the final moments of the 20th century. What followed was the kind of night that can only happen when you’re 8,000 miles away from home on a tropical island, with zero expectations. We spent hours talking at an abandoned rooftop bar, then wandered down to the deserted beach, where we lay under a palm tree and talked some more. As dawn broke, we went back my bungalow, whereupon he threw me against the wall and kissed me. It was game on, and while we never technically had sex, we spent the next two days together.
It’s been my experience that the less prepared I am to hook-up, the more likely it is to happen.
Regarding infidelity, let the buyer beware when it comes to travel flings. If you’re in a relationship, whatever your arrangement, don’t be an a-hole: use a condom. I don’t condone cheating because S.O.’s usually find out (“What happens on tour stays on tour” is bullshit in this era of social media), hearts and trust are broken, and diseases are spread. Potentially risking the life of someone you care about (or that of a stranger) is just not cool. If you’re single, be aware that your new friend may not be — no matter what they tell you. Since you have no way of knowing, in the moment, what their situation really is, protect your feelings and your health. I once had a fling with a guy, only to find out later that he was married. I don’t like being the other woman, even if the primary woman is cool with her husband screwing around.
This brings me back to condoms. Condoms don’t work if you don’t use them, and if they’re applicable to your sex life, pack them, because you never want to rely on a rusting vending machine in skanky bars or off-brands from developing nations. Of course, condoms aren’t fail-safe, nor do they protect against every STI, but they’re better than nothing. On the related topic of safety, keep your wits about you when traveling, whether or not romance is on the menu. If you’re lucky enough to get lucky, don’t trust that your new partner will be a gentleman during or after the act, no matter how charming or heartfelt he is.
If you’re single, be aware that your fling may not be — no matter what they tell you.
My best travel fling happened under the worst possible circumstances. It was September 11, 2001, and my next-to-last night in Portugal. I had just enough money left for a taxi to the Lisbon airport (my connecting flight back to the U.S. was via London). A shopkeeper with limited English attempted to explain the tragedy that was unfolding in New York, and at his urging, I called my parents from a pay phone. Dazed, I returned to my hostel, where I spent the next three hours slumped in front of the communal TV in a state of shock. Finally, a Dutch guy (who, I couldn’t help noticing, was extremely attractive), asked me, “Are you American?” When I said yes, he came and sat beside me, took my hand, and said, “Is there anything I can do to help you? Do you have enough money?”
I’m not a spiritual person, but this guy, P, was my savior for the next 36 hours (while I waited for flights to resume). He did more than loan me money — he and his friends were determined to distract me. They took me to dinner that night, and despite my protests (it felt wrong to even attempt to have fun with so much pain and suffering at home), they dragged me to a club, got me blind drunk, and we danced the night away. Inevitably, however, I broke down, and P took me to a quiet corner and wrapped his arms around me until I stopped sobbing. It was exactly what I needed at that moment.
Sometimes, travel flings can remind you that humanity still exists, even as the world crumbles around you.
While hook-ups in inappropriate places are part of the fun, vigilance is key. In college, I thought it would be fun to make out with a guy while lying on the bar in an after hours, open-air restaurant. It was a blast — until the local Federales caught us. One handcuffed hour in a janky cop car later (during which time I jabbered the only Spanish I knew: “I’m very sorry,” and “I have money”), we were relieved of all of our cash and dumped on a dirt road, forced to hoof it back to our respective lodgings.
My roommates had no idea where I was, so if anything truly bad had happened, I really would have been screwed. The takeaway: try not to break any laws, and always carry (well-hidden) cash.
And that, in essence, is the secret to a great travel hookup: Be ready for anything, and if you happen to know a few key words of the local language, so much the better.