17 People Share Their Most Brutally Cringeworthy Hook-Up Story

5. Jack

Ok. I have some pretty bad hookup stories. I’m the bad hookup fucking master. But my best failure involves an IMMEDIATE rejection. Like. The hookup didn’t quite get there. But I do vividly remember being dumb and making “all the right moves.” I had the liquid courage, Eternal Sunshine of the Spotless Mind was playing. To Freshman Me, conditions were perfect. But I talked about my ex-girlfriend for 20 minutes, before exclaiming “We should make out, right?!” I have no idea what turned her off. I’m such a nice boy. Long story short, I ran to the whiz palace and she slid my copy of Eternal Sunshine under the door. That was the day I learned the vital importance of nuance….and….you know… not dumping your “emotional baggage” on virtual strangers.

6. Jacob

The girl I had liked for LITERAL YEARS finally decides to (drunkenly) make out with me at a friend’s pool party. I knew that she didn’t really like me, but I was 19, hammered, and so overwhelmed with the whole thing that I just went for it. I was harder than I’d ever been in my life — this girl looking at me would give me a boner, actually kissing her felt like my dick was going to explode. We ended up going upstairs to my friend’s parents’ room where I fingered her for approximately 3 awkward minutes before she said she was tired and fell asleep on top of me, and I fell asleep eventually with the most painful boner of my life. The next morning we realized we had stained the sheets through to the mattress with our chlorine-and-alcohol soaked bathing suits, and spent the next day at Sears replacing them while she wouldn’t look me in the eye.

7. McKenzie

So my junior year of high school I was dating a guy who liked me significantly less than I liked him. Therefore when March 14th (international steak and a blow-job day) came around, he was persistent that we celebrate. We were in high school at the time so his mom was home and he had a fairly small house — we weren’t going to be able to do anything. So as he was driving me home for the night he requested I give him “road dome.” I was reluctant, as I had never done it before and I didn’t feel very well, but for irrational fear that he’d break up with me if I didn’t do it, I performed oral on him while he was driving. As we got closer to my house he wasn’t finished, so I told him to keep driving a little longer. I live near the ocean, so he drove straight on a road going towards the public beach. He pushed my head down to encourage me to go deeper, as we simultaneously went over a bump on the road. I gagged and then proceeded to puke on his dick. I then opened my door while the car was moving and finished vomiting. He broke up with me 2 weeks later and I won’t give “road dome” to this day.

8. Sarah

I was going down on a guy and he told me I reminded him of his sister……..



Chelsea Fagan

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

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