17 People Share Their Most Brutally Cringeworthy Hook-Up Story

15. Beth

A long term boyfriend and I were having sex and I was on top, and it was dark. And I moved my hand at the same time he was moving his head in this moment of horrible coalescence that led to my thumbnail catching the skin about a millimeter from the outer corner of his eye and scratching downward. We stopped. His facial wound made him look like a Thundercat.

This was a week before Christmas and so we had to make up a lie about how he got it to tell my family.

16. Dave

I got sucked into a molly-induced game of truth or dare at the age of 27, and somehow ended up letting a guy finger my ass for about 10 seconds because I thought that it would lead to me having sex with the girl I was really into who was also playing the game. (She was the one who dared me to do it, because she said she would think it was “so sexy.”) We never actually hooked up, and she got sober a few months later and basically cut us all out of her life because she was “putting the past in the past.” My anus will never forgive me.



Chelsea Fagan

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

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