I put myself in grad school

Nothing major tbh. But in hindsight I do wish I did a better job with my first relationship (her friend asked me out on her behalf - I said yes out of politeness. And I wasn't ready at the time).

Asked her to be my girlfriend too soon.Damn it..she accepted

I did exactly this to a woman in a well-known department store a couple of weeks ago. She was absolutely mortified, but very grateful. It’s all in the way you do it, of course.

I’ve done some pretty awful things to people in the past - usually involving cutting them loose. I will go to great lengths to protect myself, and if that means you have to not be in my life any more then you’re out. I regret hurting a couple of people, but not enough to let them back in. My sanity is worth more.

My good friend didn't think I could hurt her feelings and kept going at me about it, but I knew exactly how to do it - suggest she was a bad mother. I didn't mean it, but I just had to prove my point and be right. Hurt her so bad she didn't talk to me for weeks and I couldn't convince her I didn't mean it for months. We're good now but that was dicey. TLDR I'm an asshole 🙁

I wish I knew you in highschool. I would let you bully me every day

I have committed a long list of evil things and on that list are some points of which I assume they were immensely more worse than intended or anticipated. So to find the most regrettable one is almost impossible. In an attempt to compliment someone I made some public remark that backfired since the "compliment" turned into a racist/sexist insult when received and I had no chance to sort it out. I'm still ashamed of it though the double meaning of my wording wasn't obvious to me when I said them.

Lol you bully, one time in P.E. at school we were playing dodgeball and this kid who was autistic or something that was on the opposite team gave me his ball and then I guess I had a brain fart or something and forgot and ended up throwing it at him and got him out. I didn't plan it or do it on purpose it just kind of happened

i never did anything like that God you're a bitch :P I made my grandma cry during an argument once i felt bad about it

I don’t know that I genuinely regret much. Everything has served a purpose. But... if I had to pick one thing (in general), I would probably have to say anything that I may have said or done (consciously or not) that may have have been damaging to them emotionally/psychologically.