17 Men And Women On Their Worst What-Was-I-Thinking-Moment

We’ve all had times we’ve looked back and wondered why we did something we now find so utterly stupid. We interviewed 17 people on their most regrettable moments. Here’s what they said.
The Break-Up
The Break-Up

1. “Told my boyfriend we should experiment with bdsm. He had no idea what he was doing, neither did I, and at the end we were both bruised and sad.” – Kelly, 32. 

2. “I used to cheat off of my friend in my child psychology class in college. I was too lazy to study at the time. She found out and told the professor and I lost her (and the class) over it. Still not sure why I did that.” Michael, 25.

3. “I followed my boyfriend at the time to Los Angeles even though I knew he wasn’t in love with me. He was just trying to be nice, I guess, and said I could come. 3 weeks later and we broke up and I was stranded in LA. It sucked.” – Kristen, 27.

4. “I catfished my girlfriend to prove she was cheating on me. She was, but she found out I catfished her on OkC and she told all of her friends and people that know me and now everyone thinks I’m some super crazy internet psycho. I wish I would have just ended it when I thought she was cheating instead of digging for evidence.” – Eric, 27.

5. “I woke up to a girl jerking me off one day and I went with it. I regret it severely.” – Kevin, 25. 

6. “A guy I had a crush on asked me to share a cab to the airport after a long day of flirting and talking. I should have said yes but I didn’t. I don’t know. I still wonder what could have happened. I won’t get to see him again for a few months and I’m REALLY hoping he doesn’t have a girlfriend by the time I see him. ” – Christine, 24. 

7. “I co-signed a loan for my ex when we had only been dating for 6 months. Huge mistake.” – Brian, 32.

8. “One time I ate my roommate’s leftovers. I’m not sure what was in it but I was sick for 2 days straight after that. Learned my lesson: don’t fuck with your roommate’s leftovers.” Ryan, 25.

9. “I used to log in to my ex’s Facebook account after we broke up just to see what he was up to. I found out he was cheating on his new girlfriend and I sent her an anonymous message to look out for him. The whole thing back fired. He found out I had been in his Facebook and ended up making me look like the psycho to his girlfriend. I admit I should not have been doing that but he was obviously cheating on her! With many women! They’re still together and it still pisses me off to this day he got away with it.” – Dayna, 23. 

10. “I let my ex live with me for 8 months after we broke up because she couldn’t find a different place to live. It was the most awkward 8 months ever and only made my feelings towards her worse. I wish I would have just made her leave right away. I think we would still be friends or on speaking terms.” – Andy, 27. 

11. “I didn’t fuck my professor but we did have an emotional affair going on while she was married. I would write poems about her and bring them to the class she taught. My entire co-hort knew the poems were about her and I basically became an outcast in my grad program. Ruined my entire graduate experience.” – Megan, 24. 

12. “I cheated on my ex 3 hours before he was flying in to see me to propose.” – Tiffany, 26. 

13. “I had unprotected sex with a guy I knew was fucking around with other women and ended up getting herpes. I think herpes has a stupid stigma because it’s honestly not THAT big of a deal when you get on medication, but I’m pissed at myself for doing something so stupid.” – Rachel, 30. 

14. “I fooled around with my boss, even though it was completely against company policy. Should NOT have risked my job for that idiot.” – Emma, 34. 

15. “I fell in love with someone I knew was bad for me. He hurt me and betrayed me in all the ways I could have predicted but I stayed around for a long time with the hope things would change. Looking back I can’t believe I was such a dumbass for knowingly getting into a relationship with a jerk.” – Kim, 23. 

16. “Oh man. Last night I ate a pizza with way too many jalapenos. My ass wants to seriously know what I was thinking.” – Joe, 33. 

17. “Sometimes I look back and think about how much of a terrible person I was to my parents when I was a teenager. I know all teenagers are bucket heads and say stupid stuff, but now that my parents are gone I look back at those times and just wish I would have been nicer.” – Chris, 37. Thought Catalog Logo Mark


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