People Tell Us About Their Worst Summer Flings

I have a confession to make: I really suck at summer flings.

Of the five I've ever had, one stormed out of my house and never came back, two are now casual acquaintances, and two turned into four-year relationships.

Luckily, it looks like I'm not the only one.

It's something most of us would like to do at some point, having grown up on a steady diet of movies featuring summer romances, from brief and steamy (Danny and Sandy) to slightly unsettling (Johnny and Baby). But as the people interviewed for this story can relate, real-life summer flings aren't always that simple; we hang on too long, we develop feelings the other person doesn't have, we lose interest and drift apart, or one of us meets someone we like better.

Collected below are cautionary tales from flingers past, tales of beach makeouts and awkward partings, of heavy petting and heavy feelings, of foreign countries and fuccbois, of sex organs great and small. So for those of you having the time of your lives as you watch fall approach, and thinking about winding things down, or kicking them up to the next level, beware: they can get messy. Or worse yet, turn into a relationship.

El Monstruo — Sarah, 31

I once dated a Spanish musician for two weeks while I was living in Greece. It was basically the perfect summer fling; we would walk along the beach, sit and talk all afternoon, and make out. He wrote me poetry and wooed me with songs. We flirted while swimming and went skinny dipping at night. It was hot. It was romantic. Then one day he invited me to "have a nap" with him in his room. We started fooling around and got naked, and that's when I noticed he didn't just have a big dick—to this day it's still the most insane thing I have ever seen in my entire life. I tried to suck on it but couldn't even get my mouth around the head; the best I could do was feign enthusiasm as I negotiated drooling on it and jerking him off. When he asked me to hop on it, I just told him there was no fucking way, and that I wasn't willing to push myself to the necessary lengths (or widths) to make it happen. Just then, my phone rang and I jumped up to take the call, slipping into my dress and shoes as I went. While still on the phone I told him I had to go, awkwardly let myself out and never saw him again.

He later became a one-hit-wonder in Spain. I still have nightmares about that thing.

The King of Negging — Sarah, 35

This happened back when I was 18, and travelling around Greece by myself. I was going to university in the fall, and about to start getting serious about my life, and having a Europe Affair was on the to-do list.

I'd started hanging out with folks in the hostel, and I met this older guy from Sweden who was travelling with his younger sister. She was kind of my age, and he was helping supervise her travels. And anywhere we went, he'd come along. And he was just the King of Negging. We'd talk about feeling young and vulnerable, and he'd say, "Well, you guys aren't among the Beautiful People, but it's OK. There are other valuable things about you."

One night, we ended up being his wingmen and staying at this club with him until four in the morning, and being massively ill the next day while on this epic hike he insisted we go on. I spent two hours being violently ill by the side of the road, and he's patting my back going "See? Now you're being honest. This is the most beautiful you'll ever be." And this absolutely worked at the time, by the way. Unfortunately, he was also really good-looking, so a lot of it also had to do with 18-year-old hormones. But I'm there thinking, Oh, he's being so sensitive. He's so perceptive. Then he'd say something horrible about me again. And this sort of thing went on for what must have been ten days. And finally, it was their last night in Greece. They were taking a ferry in the morning. And I thought: "I know what's happening tonight." We'd conspired about how we'd lose his cousin, which basically involved abandoning her at a nightclub with some French guys.

And I figured we'd go back to the hostel. But he was like: No. People will see us coming back together. And I still wasn't wise enough to turn tail and run. So instead, I spent hours in the dirt of a pine grove behind a tiny church with him. It was something like three hours before he made a single move, which was to all of a sudden sit up and say: "Undress." Which I did. He's got all of his clothes still on. I go to pull his shirt up, he pulls it back down. And it must have been three in the morning when he finally unzips his pants, to deposit an entire inch-and-a-quarter of penis in my mouth. And he would have happily just sat there and had me suck it for hours. I couldn't tell if he was even remotely interested, or if he was even hard. After what felt like an hour, I was like: This is the least sexy thing I've ever done in my life. I've got the worst neck-cramp ever, I've got rocks digging into my knee. And this guy doesn't care. Finally, I just left, taking both my 18-year-old IQ points with me. They left the next day, and I thought: Well, that was a good life-lesson.

The funniest part is, I'd given him my email address, and after I got back home, I received a 5,000-word email telling me how actually perfect I was, how incomplete he'd been since moving back to Sweden, and asking if I'd move to Sweden and start a life with him.

I could never keep a straight face long enough to write him back.

From Mexico, With Love — Shari, 25

When I was 21, I met a guy from Mexico. At the time, I was cocktail waitressing at the sleaziest bar in Vancouver. We hit it off, and ended up hanging out a couple of times. I took him dancing during Pride, and ended up taking his virginity, while on my period (yikes!) and a week later he was back on a plane to Mexico. Before he left we talked about him coming back to Vancouver the following summer, and I went along with the conversation because it was sweet, and I figured it would be kind of heartless if I told him we would probably never see each other again. He gave me a cross necklace (!) and we parted ways, and I really didn't think much more of it. Then, the following summer, I got several messages and calls. He had arrived back in Vancouver—he'd actually followed through with our conversation. Unfortunately, I was dating someone else at the time so I ended up ignoring him. Oops.

2 Girls, 1 Crush - Catherine, 25

My boyfriend and I had a summer fling with a girl a couple years ago.

He'd had a crush on her for years, and the two of them had kept in touch sort of casually, and I'd always known her as this sort of mythical unicorn creature and I'd always felt a little bit threatened. But one afternoon we all went out for drinks, and when I met her she was actually really cool, and the two of us really hit it off—probably better than the two of them ever had, to my boyfriend's chagrin. She was hot and fun, and very single after a long engagement that had ended in some serious infidelity. We all had a great time, trying to help her pick up guys while we were out, and it had come up briefly at one point how she'd never want to be nonmonogamous like us, but that she'd always wanted to be the Guest Star in someone else's threesome.

You can imagine how the evening ended.

We saw her three or four more times—sometimes sexually, sometimes just as friends. The bulk of it happened during the summer, but we even took her out with us for Valentine's Day, and we all bought each other presents. And it was great: you and your boyfriend having a crush on the same person.

Of course, inevitably she met someone, and that was the end of it. And I remember being really sad at the time. And feeling kind of stupid, because we'd made such a Rookie Mistake. She was the first time I'd ever had a legit crush on a woman, and we all had fun together, and so of course we'd started to think it was more than it was. She was never all that comfortable with the idea, and dating a couple wasn't something she'd ever wanted long-term. We'd just let ourselves get carried away.

We don't see much of her anymore. We're both glad she's in something that makes her happy, but I still kind of miss her sometimes.

Summer Lovin' — Taya, 29

I had a summer fling with a coworker/fuccboi that lasted eight months too long.

He was constantly pestering me for a date. I finally gave in because he was just so damn good looking. At first I was in it for the fun but, but then after two months, as the summer ended, we had the exclusivity discussion. Of course, all of my friends and roommates were super skeptical that this was ever going to work, and I knew he would be trouble in the end, but we were both really into each other. What could possibly go wrong?

As time went on, and summer turned into fall and then winter, I started to suspect he was cheating. He had this pet rat, and one night I stopped by his house after work to feed it, and his roommate was there, so I stayed and chatted for a bit. My fling-turned-boyfriend had said he was at his buddy's house playing video games late and would come by later. But by 2 AM, I was still at his place hanging out. And suddenly we hear girlish giggling at the front door.

My now-boyfriend walks in, sees me sitting there, and immediately ducks back out. And from behind the door I can hear him frantically whispering something. Then he opens the door and walks in with some other chick—both of them dressed to the nines. And of course it's awkward as hell for everyone. He offered to get drinks and this girl just scoffs and storms into his bedroom… because of course she already knew where it was. I can hear her on the phone, upset, and my boyfriend follows her into the bedroom. She left very quickly after that. At which point, my boyfriend proceeds to sit next to me on the couch and pretend everything is OK.

I was so livid I couldn't even speak. I finally found my legs, got up, and walked out without a word. I was mad at myself for being stupid enough to get drawn into such a toxic relationship. The worst part, though, is that after about a week I fucking let him back in.
For another month.

And that's why you never date the summer fling.

Something's Fishy — Bryan, 33

I started hooking up with this girl one summer; we'd been friends for about a year, always very flirty, but we'd always both been seeing other people. Eventually we were both single at the same time, and started hooking up. We were in this sort of grey area where we were sort of dating, I guess, but after about three or four weeks she confessed that she wasn't really feeling the emotions she'd expected to feel. That she enjoyed having sex with me, but there wasn't anything deeper there.

My response was, "Oh thank God, me neither."

But neither of us had anything else really going on at the time so we figured why not keep having sex? Neither of us had ever had a summer fling. Why not have a summer of chilling out and fucking each other? And it's weird because it actually worked for awhile. We were honest with each other. We both learned new things and weren't afraid or nervous or all caught up in emotions. It was a really fun time.

Towards the middle of the summer she told me about a new guy she'd met and was kind of into. And there was no jealousy. In fact, I helped her come up with date ideas. I was starting to get to a place where I was thinking about finding someone to date myself, and we both knew that things were probably winding down.

The last time we hung out, she came with me to buy a pet fish. We walked across downtown only to discover that the pet store had moved another 20 minutes walk away. She complained that she didn't want to walk anymore and wanted to go back to my place and have sex instead. I remember weighing it: fish or sex? We'd already walked for 20 minutes, and I didn't want to go home empty-handed. But finally, she declared that if I didn't want to go back home, she was going to bail.

I bought the fish.

And it's just as well, really; if hooking up and buying a fish are equally appealing in your mind, it's probably time to call it a day.

Numbers Game — Jennifer, 33

One summer, I got super horny late at night, and decided to see how many summer flings I could have in a single evening. So I put an ad on Craigslist seeking multiple men for a gangbang—as you do. The gangbang never happened, but I ended up making arrangements with five different men, all of whom came by one by one. I didn't want to parade everyone past my roommates, so I just met them in the alley behind the house, and we had sex in this garden shed out back.

You ever wonder what kind of people answer those Craigslist ads? One was a redneck from the suburbs named Rick. But the final guy was super fit and fucked well. Long story short, he's my boyfriend now. We've been together three years. Which goes to show that sometimes summer flings can work out great. You've just got to play the numbers.

He later told me that his first thought upon meeting me was he was grateful I wasn't a dude.