17 People Share Their Most Brutally Cringeworthy Hook-Up Story

I recently asked my friends and followers to share their most embarrassing/cringeworthy hookup stories, and they did not disappoint. Some names have been changed, but THE PAIN IS REAL.

1. Jackie

My first boyfriend and I were dating for about a year before we finally had sex, and we decided to do it on the floor of his family’s basement rec room, which was right next to the stairs that led down from the living room. About halfway into our virginity-losing session, his mother pops her head in to ask if I can stay for taco night, and we both scream at her to not come down the stairs. She knew exactly what was going on, and needless to say, taco night was ruined that week.

2. Lily

A dude and I had been talking online for like, way too long. We both knew we were only ever going to hookup; there was no real chemistry, just a moderate physical attraction that was pretty hot at the time but was always doomed to quickly fizzle. So we’ve been talking for almost 3 weeks and FINALLY homeboy invites me over. He does so on a Friday night when I’ve been drinking. Heavily. I’m hammered and have been for a while so yes, I thought jumping in a cab at 2 am to meet this dude for the very first time ever at his place was a great idea. Not my finest moment but we all have lapses in judgement.

I arrive and thankfully he’s just as drunk as I am. We proceed to have the sloppiest, most awkward (but still kind of fun) sex I’ve ever had, before or since. Everyone finishes, we pass out in his bed, and I wake up in the morning with a semi-intact, if blurry, memory of the night before.

While dude is sleeping I stumble to his bathroom to try and salvage last night’s makeup so I can walk of shame myself out of there and much to my surprise my face is covered in blood. On my mouth. On my cheeks. On my nose. What the hell? And then it dawns on me. I’ve started my period a day early and we were both too drunk to notice. I’ve started my period a day early and at some point in the night I let this stranger go down on me and then I made out with him and then I slept in his bed with nothing to shield his poor sheets from my perfectly natural but so poorly timed womanhood. And let me tell you something about my period: it does not fuck around. That shit shows up with a vengence and makes no apologies. So I’m in trouble.

After I clean myself up I creep back in to the bedroom to assess the damage. Sure enough, it’s everywhere. His hands. His dick. His face. His sheets. Everywhere. But he’s still out cold and this is the first (and most mortifying) time I’ve anonymously hooked up with someone so I panic. I grab my things and I bolt.

I get home. My phone had died in the night so I plug it in. A text comes through from the dude: “I was going to double check that we used protection last night but considering what I woke up to that seems like a moot point, wouldn’t you say?” He was trying to be funny. I haven’t talked to him since.


Chelsea Fagan

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

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