17 People Share Their Most Brutally Cringeworthy Hook-Up Story

17. Thea

This isn’t so much cringeworthy as it is just plain horrible, but it’s my biggest regret so I must (anonymously) share. I had been secretly in love with for my boss for years, and always suspected that he was, too. We would flirt and flatter each other while drunk at company parties, and hint around our feelings, but it never went anywhere because he was with this girl I couldn’t stand (of course). One day, while REALLY drunk at a rooftop party, we start making out — in FULL VIEW of the other employees who were still at the party, too. They didn’t say anything at the time, but I knew things would never be the same with them again. (Drunk me didn’t care, though, she was just too happy to think about it.) We ended up getting a hotel on the way back (a Sofitel, because I am a classy floozy) and had incredible sex until literally six in the morning. But as soon as we dressed and left, it was like someone had turned off a light switch. He barely spoke to me, and the other employees who had seen us were icy in the office. When I tried to bring it up once a few weeks later to him, he all but pretended not to know what I was talking about. My heart was totally broken, and I began to realize that he didn’t have unrequited love, he just wanted to fuck me. I left the company shortly thereafter, and recently heard that he and his girlfriend at the time are getting married. I have honestly considered burning down that office building.



Chelsea Fagan

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

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