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Embarrassing, Cringe-worthy and Downright Hilarious Hookup Stories

Awkward is practically my middle name. I probably do more embarrassing things in a day than most people do in a month. But everyone, and I mean everyone, has at least one brutally embarrassing, awkward, or cringe-worthy hookup story. I recently reached out to my peers to share their stories and they did not disappoint. The following are 12 of the most painful, or just downright hilarious, sexual encounters that I had the pleasure of hearing about.

All names have been changed to protect the privacy of those involved. 


Sophomore male

A little back story: I’m a totally-straight musical theatre major, which was very rare at my college. I was at a Christmas party with this girl that I was already friends with for a couple months and she wanted to use the bathroom in my room (which I suggested). We got up there and started making out. Next thing I know she’s naked on my bed and I’m going down on her. She starts with the usual satisfied moaning and then lets out a series of “You’re not gay”s. That’s right. As I’m going down on her she starts repeating “You’re not gay” over and over again. I didn’t know my sexuality was ever in question but I’m glad I was that good that it confirmed I was straight.


Sophomore female

Over the summer I had a short fling with a guy from work. I went over his house and slept over. In the morning I really had to pee, so I tiptoed out of his room to the bathroom right across the hall. The door was cracked so I just pushed it open, and there was his dad… Pooping. I didn’t say anything, just ran back to the guy’s room and laid in bed. Ten minutes later there’s a knock at the door and his dad yells, “It’s all yours!” I didn’t move. Another ten or fifteen minutes later there’s another knock and he goes “Son, tell your lady friend she can use the bathroom!” I was mortified. Long story short, I never used his bathroom.


Sophomore female

 I was hooking up with this girl and had her handcuffed to my bed when my mom came home. I went downstairs to talk to my mom and forgot that I wasn’t wearing pants. If that wasn’t awkward enough, I also left the girl handcuffed in my room.


Freshman female

Even after explicitly telling my boyfriend to not finish in my mouth he did… I was so furious I started yelling and spitting everywhere. Needless to say, there were no more blowjobs for quite a while.


Sophomore female

A few months ago my boyfriend, his roommate, one of my housemates and I were playing Apples to Apples in her room. My roommate’s boyfriend was visiting so my room was occupied. After an hour of Apples to Apples my boyfriend and I went downstairs and started making out on the couch since my room was off limits. Shortly after, we heard the door upstairs slam. We kept kissing and I end up completely naked. So, of course, this is when his roommate walks downstairs and asks for a condom. While I’m totally naked. Turns out they started having some fun of their own, hence the door slam. All in all, it was a pretty quality night, although I got a lot closer to my boyfriend’s roommate then I’d planned on… And since then he has walked in on my boyfriend and I having sex or about to have sex at least 3 more times.


Freshman male

[Back in high school] we were making out in class and she had braces. So needless to say I ended up with a cut on my lip that wouldn’t stop bleeding and had to go to the nurse. Everyone knew.


Senior Female

This summer I hooked up with a guy who had just graduated with his Master’s degree in Public Health. I could tell he had a health background when we were hooking up for the first time because the entire time he just kept asking “You’re clean, right?” referring to me not having any STDs. I just thought it was so awkward and so funny at the same time. I couldn’t do anything but laugh every time he asked because he had to have asked me at least a dozen times and I had never been asked that before.


Freshman Male

So, I was hanging out with a group of friends a while back and it was one of the first times any of us had drank alcohol. We all got pretty tipsy and decided to play truth or dare. This super religious girl is on my left and one of the girls there says to me, “I dare you to massage the person to your left.” So I start and she starts making all sorts of weird noises and starts taking off her clothes and everyone leaves so it was just her and me. So, she takes me upstairs and when I thought we were about to hook up she starts rubbing her body against me but not kissing me. I try to kiss her and she turns her head away. Soon I stop and ask her why she isn’t kissing me and she says, “I don’t want to kiss anyone but the boy I love.” So we rub against each other a little longer and I keep thinking this is messed up on her part and then she just fell asleep. So that was one of the weirdest times I tried to hook up, I guess.


Sophomore female

I don’t drink very much, nor do I have much experience with guys. Well, one day I went to a party and ended up sitting next to this really cute guy all night. I was super drunk so I think I was actually managing to have a decent conversation with him. Finally, he leans over to kiss me and I go, “Nahh,” and reject him. Nah. That’s all I said. Nahhh. I still can’t believe I did that. I also then sprayed someone with a fire extinguisher so it was a pretty memorable night.


Sophomore male

Long story short, last year my friend got insanely drunk and brought this girl back to his room. She was giving him a blowjob and he fell asleep. He felt so bad that he sent her an apology text the next day. They ended up being at the same party the next weekend and I guess the apology was effective because he brought her back to his dorm again. And fell asleep. Again. With the same girl.


Sophomore female

We were both super drunk at a party so we went out to the front porch and started making out. I gave him a blowjob and as he was about to go down on me his neighbor walks by and says, “Aw, sh*t, not again.”



Brett and I were actually having a really lovely time when it got too cold to be outside so I suggested that we go into his car, purely for the purpose of being warm. For some reason he wanted to park at a dairy bar, which is right next to a main road. One thing led to another until I was half naked in the back of his mother’s car. I remember he asked what I wanted to do, and when I awkwardly tried to answer he was like, “’Cause my pants are really tight right now but I kind of don’t have a condom.” So I was, like, doing my thing when all of a sudden, a car pulled in a few spaces next to us. He assured me that nobody could see anything and kind of made me keep going, which was awfully rude, but, whatever. Then another car pulled up. Only, from this one, some sort of weird, squawking sound was coming out. We sat there and watched while the two cars actually, physically, exchanged a bird. A freaking bird. After they left I was completely done, but Brett clearly still had a bit of a problem, so I told him he could finish himself off while I kind of just sat there. But, because some higher power has it out for me, a car with flashing red and blue lights pulled up riiiight next to us. Pretty sure the police officer saw my boob. After that exchange I made Brett drive me home and the last thing he said to me was, “Damn, I really wanted to play Pokémon.” Also, I left a brand new shirt in the back of that car that I really liked and never got back. So it was quite an experience.


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