People Share Their Juicy Vacation Hookup Stories


I'm a complete sucker for vacation hookup stories. After all, people travel to foreign destinations either to find themselves or to be somebody else for a while, both of which can bring out our adventurous sides. So, I asked people to tell me about their juiciest vacation hookups, and their stories did not disappoint.

Most singles have had a one-night stand on vacation at some point, according to a MissTravel survey. Plus, nearly 90 percent of us say we'd be more likely to hook up in a foreign destination. According to a survey from the dating site Happn, the most common Spring Break cities for the app's users pick people up are Miami, Vegas, Cancun, New Orleans, and Punta Cana, Dominican Republic. Another study by Tinder found that the most popular cities for users seeking dates abroad are London, Paris, NYC, Berlin, and Moscow. All good choices. But the city where people are having the most sex with strangers, according to an Ann Summers survey, is Ibiza, Spain, and based on these stories, maybe New Zealand should be added to the list.

Sometimes, vacation hookups can turn into relationships. Other times, what happens in Vegas (or Miami or Ibiza) is meant to stay there. Either way, they can make for great stories. Here are some vacation hookup stories you can vicariously live through. You're welcome.


Sheyla, 30

"I'm Brazilian, and back in 2014, I decided to come to New Zealand. Tinder was obviously a way to meet new people, and I ended up having a first date with an American guy. I went back to Brazil, but we managed to keep chatting. Long story short: our second date was in South Africa. I spent 10 days traveling around the country with a guy I barely knew, and it is up until now one of the best experiences I've ever had. Relationship didn't work out, but we managed to stay friends occasionally."


Hannah, 26

"When I was 20, I spent the summer in New Zealand and a few days in Fiji. Well, there was Jonny Armstrong, the Irish guy whom I met on a pub crawl and later followed me to other cities in New Zealand. We only saw each other on nights when I had to get up early to catch a bus or flight, so I think the constant feeling of me leaving just when we found each other again kept enticing him to find me again.
There was Ahmed, the Iraqi guy in New Zealand. He was probably the most interesting and unexpected. There was Corey the American in Fiji, who tried to have sex on the beach but it was really unpleasant, then we went back to my hut, and after finding out he didn't have a condom, he went and searched the whole resort for condoms.
There was Tyson, an Australian in Queenstown, New Zealand whom I paired with to win an office chair racing competition at a bar. His beard was painfully scratchy, and at the end of the night, outside the door to my room in the hostel, he gave me his number and said to call him the next day. I had already decided I didn't want to see him because his stubble hurt too much, so I said 'I don't make calls, I receive them.' I didn't receive a call from him after that!"


Catherine, 26

Last year, I went on vacation with my parents in Hawaii. ... I matched [on Tinder] with an absolute hottie who was visiting Maui for the holidays, just like me. He was also from California, and it turned out he was a drummer and music producer who was in town playing a concert. We chatted a bit and hit it off... so we decided to meet up later that night for a drink.
We agreed to meet at his hotel bar around 9:30 p.m. I snuck the keys to my parents' rental car that night and left to meet up with him. As it turns out, the bar had already closed, so we ended up just hanging out in his hotel room. I knew I was either going to get murdered or laid. Lucky for me, he wasn't the murdering type, so we shared a couple cocktails in his room. After the alcohol started to kick in, we ended up going for a risqué romp under the Egyptian cotton sheets, where he discovered my tattoos and I discovered his six-pack abs.
Afterward, it was late, and I needed to get back to my family's condo before they found out I had taken the car. I snuck out of his hotel and headed downstairs to get the keys from the valet around 3:00 a.m. I handed the attending valet the ticket for my card, and he left to find my keys. He returned from a back room a few minutes later with a perturbed look on his face. "Are you sure you parked with us?" As it turns out, the valet had LOST MY KEYS.
I was living a walk-of-shame nightmare: My makeup was all over my face, my hair was in knots from my — ahem — interlude, and I was stranded in the lobby of the golf resort because the valet had lost my car keys. Eventually, the attending valet and I ended up on our hands and knees in the parking lot, trying to find my missing keys — at 4:00 in the morning. Finally, after the most embarrassing and hilarious hour of my life, we found the keys: They had simply been put in the wrong drawer in the valet office.
I snatched the keys from the valet and raced back to the condo, arriving just before my parents woke up around 5:00 a.m. I was delirious from exhaustion and the hilarity of the whole situation, but I texted the drummer to thank him for a great night. As it turns out, we both had such a great time that he invited me back the next night — and this time, the valet took great care not to lose my keys."


Kelly Chase, Co-Host Of The Workationing Podcast

"After a bad breakup I decided to take an impromptu vacation at a resort in the Dominican Republic with one of my best friends. I was feeling pretty bummed about my dude situation back home, so I was definitely in the mood to do a little flirting and possibly have a little vacation fling while I was there. As luck would have it, on our first day there, we had to switch rooms, and the gentleman who was sent to help us move our bags was just ridiculously good-looking and seemed to take a shine to me.
I'd had a few breakup cocktails at the swim-up bar earlier in the day and was feeling bold, and the next thing you know, I'm making out with this dude in the kitchen of our suite. It was a fun little encounter, and we made plans to meet up later. However, that's when things got weird.
A few hours later, he slid a lengthy love note under my door, and the next day — when I still hadn't returned his texts because I was thoroughly weirded out — he somehow got my friend's phone number from our records at the front desk and started calling her non-stop to try to speak to me. What started out as an impulsive vacation makeout quickly devolved into a full-on stalker situation that made the next few days super uncomfortable. Lesson learned: be more particular when seeking out a vacation fling."


Kate, 28

"A few years back, I was in Cancun for spring break during college with my two best friends. It was one of our last nights, and I was getting frustrated because I had only made out with one guy all week and he wasn't even a good kisser. To start out the night, we went to a tequila bar, where I kept ordering us rounds of these huge, sharable drinks. We were about to leave when the table next to us ordered us another. My two friends had had enough, and me never being one to waste, I finished the entire thing myself.
We somehow made it back to the hotel (I remember falling asleep on the guy next to me on the bus) when I got my next surge of energy. I wanted to go down to the pool bar, so we made our way down there. It was after 2 a.m., so it was closed, but there was a group of guys that were down there, too.
We ended up sneaking into the bar (they had zero security — it was basically a liquor stand without even a lock) and helped ourselves to some vodka. Given that I was on the Rugby team and I had tequila, which makes me want to fight, I started challenging each guy to a match. One took me up on it. We went down to the beach and started literally wrestling. Soon, wrestling turned to sex and before I knew it, I had sand in places I still regret to this day. Our friends were just up on the shore, too, so I'm sure they saw the whole thing!"

These just go to show that crazy things can happen when you get out of your comfort zone. They definitely make a compelling case for asking out that cute person you see on the beach during your next break.