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The original was posted on /r/tifu by /u/Dull-Energy-7918 on 2025-07-17 15:25:51+00:00.

For context, I am not good at remembering faces. Especially the faces of people I only went on a date with once. Early in my college career, me and my current boyfriend had a rough patch and were broken up. After a few months of going through the five stages of grief with my friends, they advised me to do what any lonely and sad girl would do; go on tinder.

I do just that and after a string of mixed experiences, I matched with my future boss. He was an odd nervous fellow; mostly the type to ask a string of questions and not add much else. Apparently we had some classes together, hence why he was excited to match with me. But I didn’t really vibe with him. So after the date, I politely told him that I wasn’t entirely interested. He pushed on asking why, and I said I was gonna put a hold on dating for now and focus on myself.

At least that was my original plan. Life happens, and my boyfriend and I reconcile like a week after that last date in a very romantic way. He starts walking me to class again, and then suddenly I get a very long and bitter text from my last date. I didn’t spend too much time reading and promptly deleted the text and blocked him.

Fast forward to the present, the last boss at my company quit. I was offered his position, but I wasn’t quite ready for it. So they put out the position to the wider job market. And wouldn’t you know! My date from years ago applies. He seemed good on paper, having all the credentials and personality to fit the company culture. But then I fucked up. He told me that we knew each other. I should have probably looked deeper into that statement before moving forward with him. But honestly, I just wanted to have the managerial responsibilities off my back.

Unfortunately, I only remember when I found his cell number was on my block list. And now, with him as my boss, he’s making my work life unbearable. He dismisses every advice or statement I make. He gives me impossible deadlines, and recently at our 4th of July party, he had the gall to imply that I missed out for picking the wrong guy to date. Bro, the only mistake I made was giving you the time of day in the first place! Don’t worry, I’ll get HR on your ass soon enough.

TLDR: went on a date with a nerdy guy in college while I was sad from a breakup. I let him down by telling that I was gonna work on myself. Life happens and I get back together with my boyfriend. The nerdy guy sends a bitter text. I forget about him and I unwillingly allow my company to hire him as my boss. Now he’s being an unbearable boss and I have to tell HR to find a new guy.