13 Women Confess Their Most Awkward One-Night Stand Stories

Let’s be honest: sometimes sex is a magical and special act between two people deeply in love, but sometimes it is a sloppy and awkward encounter between two people who may not know each other’s last names.

This article is about that second kind of sex, in all its funny (in hindsight) glory. Cringe with me as 13 brave women spill the beans about their most awkward or memorable one-night stand.


1. “I went on a date with a guy when I was living overseas and we ended up back in my apartment. He offered me a back rub (because of course he did) and I was tipsy enough to agree. I was on my stomach, with my shirt off, when I suddenly felt something wet on my back. Then I heard the sound of a spray bottle being used. I couldn't figure out what it was until the smell hit me. It was Febreeze. I was getting a Febreeze rub down. (He had never seen it before and thought it was spray lotion? I guess?). I smelled real, real fresh afterwards.” -- Bianca M.

2. “In college, I had a hook-up with a friend of a friend visiting from out of town. When he left, he left me this really cheesy 'love' note. I remember something about ‘fate played its diamond-studded hand’ in there. He also had the nerve to call me when he was visiting again TWO YEARS later! At 3 a.m.!” -- Heather L.

3. “I had known this guy for a while and we were just friends, until one night we just decided to go for it. But then he whipped 'it' out and it was the size of a baby's leg and I was all ‘oh hell no!’ And then I took a cab home!” -- Melanie W.

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4. “I met a guy who wanted to hook up, which I might have gone for. Might have, if he hadn't said, ‘My name is Steve, but my friends call me Meat Stick.’ Thank God in my inebriated state of mind I thought OMG! and ran away.” -- Rebecca T.

5. “I was with a guy once that all of my friends only know by the nick-name ‘Baby Carrot.’ Poor guy.” -- Cassie G.

6. “So I was in high school and making out with this cute guy and I had no intentions of having sex, since I was a virgin. But one thing led to another and I did! It happened so quickly I wasn't even sure it happened. Back then I was too young to realize he was just, ahem, 'done quickly' and then he left immediately afterward. I ended up getting so much crap from people since we had not been dating that I never spoke to him again. I avoided him like the plague and the experience stayed with me for years. I was angry at him for acting awkward and everyone was talking about us so much (thanks to one loud-mouth friend of mine!) that we avoided each other for the remainder of high school!

"Fast forward fifteen or so years ... I'm divorced and a mom and back in my hometown camping with old friends, and there he is!! Eeek! I was drunk so eventually brought it up with him. I was laughing about how awkward it was when I realized he left quickly because he was embarrassed since he, well, finished so fast! All these years I hated him for acting so weird and leaving and now I realized he hated me for avoiding him and telling the whole world he was a 'fast guy.' We laughed so much we fell in love and now are married with four kids. It was a crazy ride but I wouldn't have it any other way!” -- Laura N.

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7. “I was nursing a serious broken heart and ended up drinking a little too much at a club and going home with a guy I met there. We started to make out when I burst into tears and grabbed him by the shoulders, forcing him to look into my eyes. As he squirmed uncomfortably, I demanded that he promise to never, ever leave me and that he’d never cheat. Given that we had only known each other for three hours, it isn’t surprising that I freaked him out so much that he left without even getting to second base.” -- Louise K.

8. “I’ll just say this: If you decide to hook-up with your brother’s roommate, make sure that the door is locked and your brother is not home. Or else you might hear your brother hooting and hollering at the door, not realizing that the sex sounds he hears are coming from his baby sister. AWKWARD.” -- Tammi C.

9. “I had recently gone through a bad breakup but had recently started dating this guy I met on an online dating service. We'd been dating a few weeks and he'd already shown a few red flags. So, anyway, he never showed up one night for a date, but it was fine by me because friends invited their friend Chris along. Well, fast forward through the evening, and Chris and I can't stop talking to each other and I'm basically ignoring my friends. In a drunken, brazen moment I decided I was going to have a one-nighter with this tall drink of water. We headed to his place when friends drove by and saw me walking down the street with this guy and rolled down the windows and yelled ‘Whooo, get some Katie!.’ I was so embarrassed, but still determined to become a sexually empowered woman.

This night occurred eight years ago this April, and I still haven't had a one night stand. Not only did I marry that guy, but he wouldn't have sex with me that night because he wanted to get to know me and hopefully start dating.” -- Katie L.

10. “When I was in college, I met a charming older man at a bar one night and ended up hooking-up with him. That night wasn’t amazing, but was fine enough. The awkward part was when I showed up for my new campus job a few weeks later and realized that I’d hooked up with the very married director of financial aid. Ugh.” -- Sarah F.

11. “I met a guy online and went on a decent first date with him. I was feeling the chemistry so went back to his place for some making out, which started off fine, but then he couldn’t get it up. He asked if I would mind if he turned on some porn, which was kind of weird to me but I wanted to be adventurous, so I said okay. It got weird when I saw that he had a very, very large porn collection and all of it was Asian women. I am not an Asian woman. I left pretty quickly.” -- Janelle P.

12. “I fool around with a guy (Ian) after a party at his apartment. I wake up the next morning and he's super nice and cuddly, and I realize I don't want to be with him. He invites me to go out with his friends the next night (who are my friends too). I join them, and then pull one of them aside and say: 'I don't really want to get into a relationship with Ian' and my friend says, 'I don't think he's into you, either," and I look over and Ian is hitting on the girl who became his wife!” -- Willow A.

13. “I was hooking up with this guy who had no relationship potential. He was super-hot but dumb as a bag of hair so I knew it would just be a one-night thing. We were having sex and he was going and going and going. It was lasting forever and I was starting to get sore and bored. He was starting to get really sweaty and eventually drops of sweat were falling off of his face and landing on mine. I was getting his sweat in my eyes, my mouth, it was awful! No boy is cute enough for that.” -- Susan V.

I don’t know about you, but reading this list makes me very glad to be married and to have my awkward hook-up days behind me!

What is your most awkward one-night stand story?

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