17 People Share Their Most Brutally Cringeworthy Hook-Up Story

13. Sara

Freshman year of college I went over to this guys place that I had met the night before. Mind you this was a freshman dorm. It was the middle of September and I was in a crop top and a mini skirt. He brings me upstairs and we start talking, and he mentions that he’s a virgin, and I let it be known that we will not be having sex. So we sit on his twin bed (it was a double…so his roommates bed was about 2 feet away) and he tells me about his interests and we watch Superbad. The window was open, and there was a warm draft coming in but he suddenly mentions that he’s freezing and gets under the blankets. I get where this is going, and next he asks if it’s okay if he takes his pants off. He lays down and I straddle him while giving him a dry handy, we begin to make out and he doesn’t go for anything below the belt on me. About 10-15 minutes into it he’s laying back with his eyes closed, hands behind his head (like when you do a sit up), and starts breathing in a way that can only be learned in a Lamaze class. A few more minutes go by…and he never opens his eyes…so I start getting tired and turn my head to see Billy Blanks’ Tae Bo workout playing on the TV. I begin mimicking the rhythm of Billy’s motions with my hand job and realize how ridiculous this is. This goes on for at least another 20 minutes and finally about an hour into this really weird hand job we hear his door handle begin to shake. He shoots up and yells STOP while I slink back on my shirt and start laughing hysterically, in walks his soaking wet roommate (one of those rainy, humid nights) who happens to be a casual acquaintance of my friends who I met for the first time that night; and still a friend of mine to this day. I say hi to his roommate while laughing, and this guy just looks mortified. He walks me downstairs to leave me with the most awkward side hug, and then I remembered sometime during that hand job he asked if we could have sex next time and if I liked doggy style. I avoided him like the plague, and he tried to get in touch with me over Thanksgiving break but I had just finally worked out my other arm to be of equal strength after that tae bo hour long session.

14. Callie

A few years ago, I was at a friend’s bachelorette party at this terrible bro bar where we were all hanging out being WOO girls and having a grand old idiot time. A bachelor party showed up shortly after we did and we ended up kind of hanging with them for most of the night. One of the dudes and I kind of hit it off, which led to us making out on the sidewalk at 4 am, which led to me inviting him back to my apartment for some sex. This was literally the second time in my life I’d done something like this. We got to my house and my cat was FRANTIC, running back and forth and yowling like crazy. I shut her out of the bedroom but she was determined to just run around and yowl. Finally, I let her in, thinking that would calm her down. It did not. Meanwhile this guy’s boner is like :(, so finally I figure out that she’s upset because there is a pigeon roosting right outside my window and she really really really wants to kill it. The hookup continued anyway. The end.



Chelsea Fagan

Chelsea Fagan founded the blog The Financial Diet. She is on Twitter.

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