What You Need To Know About Vacation Flings

Just like in your regular life, you have to put yourself out there if you’re going to meet someone to have a vacation fling with. Staring at your phone or a book is not likely to get you laid.

“Chat up locals, chat up fellow travelers, and generally go out of your way to be as outgoing as possible,” Figueroa says. “Be more outgoing than you usually are, so you put yourself in a position to meet someone new. Take the initiative to chat up someone when you normally wouldn’t. You might not hit it off with the people you connect with, but they might introduce you to someone you do hit it off with.”

“It’s very likely that wherever you’re visiting has a specific venue, or even a part of town that is notorious for being a place where people who are looking for flings or hookups congregate,” Figueroa says. “It might be the pool of the hotel you’re staying, a bar that caters to ex-pats and tourists, or a nightlife strip. Wherever it is, go there.”

“Whatever your preferred dating app, try using it while on vacation,” Figueroa says. “Be sure to specify that you’re visiting and, if you’re feeling bold, be straightforward about the fact that you’re looking to meet someone while you’re in town. You might get lucky and meet someone — you might not — but at the very least you’ll increase your odds of finding someone looking for a fling.”

As a general rule with any kind of dating, it’s important to always be honest — and be nice.

“If you do meet someone who is down to have a fling with you, be upfront about your intentions, whatever they may be,” Figueroa says. “There are so many people who are looking for the same things as you, and honesty goes a long way toward finding a fling. Best case scenario, being upfront will lead to a fling. Worst case scenario, you get rejected and can move on to try to find someone who is interested in having a fling with you.”

Sometimes vacation accommodations are not fully accommodating to hookups. So get creative! Be open to having sex in places that you might not consider suitable back home. Just be aware of the laws and social mores of the place you’re visiting so that you don’t end up having to add bail money to your vacation bill.

The same rules of online dating or picking up someone in a bar in your daily life apply to vacation flings. Tell someone where you’re going. Make an exit plan, in case you need it. Bring a phone charger.

“That goes for both using protection, but also about putting yourself in sketchy situations,” Figueroa says. “If you’re on vacation in an unfamiliar part of the world, keep your wits about you. If you’re going home with someone, tell a friend where you’re going."

Condom quality differs in different parts of the world, as does condom etiquette. Avoid risking your vacation lover not having them or only having ones that aren’t great quality by bringing your own. I recommend Lovability condoms because they come with awesome carrying cases that will protect the condoms in your luggage and your handbag.

I’ve had exactly one vacation fling and it was awesome. I met this guy in Rome who was totally wrong for me but so lovely and spent the next week traveling around Italy with him. We had sex in random places; held hands walking through ruins; and when he left to fly back home, I spent a day crying and eating gelato in the parks of Milan. It was like a goddamn rom-com and it was glorious.

I really believe that one of the reasons that mini love affair is one of my favorite memories of a lover is that I let myself fall for him, with the full knowledge that it would a very limited love. Knowing the limits of our relationship allowed me to be intense and a little crazy and, yeah, a little in love. I’ll never forget it.

I’ll admit — I didn’t cry for very long after my lover left me in Italy. I also didn’t try to Skype call him or text or any kind of social media. Granted, this was 10 years ago, so the options were more limited than they are today, but it was a conscious choice. I knew our affair belonged where it happened: In Italy, not back home. “Don’t get too attached,” Figueroa says. “Vacation flings can be a fun, temporary break from reality. Sometimes they turn into much more, but very often, they don’t. You might reconnect down the road, but don’t plan on it. Embrace the moment for what it is, and don’t try to turn a fling into something it’s not, and can’t be.”

Are your expectations still in check? Awesome. Now go, book a flight, head out of town, and know that you’re fully prepared to embark on an awesome vacation fling.