What Is One of Your Biggest Dumb/Regrettable Moments That You Look Back On?

Curious to hear about some of the dumb/regrettable moments people have had in their lives.

I'll start. Crack open a cold one and enjoy the show. A few years back I was a sophomore in college and had a girlfriend (now ex-girlfriend) that went to my school who I dated for a few years through high school and up until sophomore year of college. Things went rapidly downhill between us in college because she wanted the "college experience" and I wanted to stay together (read: me being a simp).

I'm sure a lot of people have been in my shoes where you thought this chick was the one and then you get hit in the face with reality. I remember she had some "guy friends" that would constantly hit on her and talk badly about me behind my back to her. She would "defend" me by letting me know about it when I saw her but when I asked her to just stop talking to them, she would always come up with some excuse like she didn't have enough friends to begin with despite joining a sorority. 

It got interesting when I finally went to confront one of the guys and he was nowhere to be found. I even texted him since I had his number from a while back and he denied everything. I went to some of our "mutual friends" and told them I wanted to talk to him which was relayed back to him as I'm coming to beat his ass. 

Next morning I was at my girlfriend's apartment when I hear a knock on the door. He came with three other friends (one random dude who would be at my girlfriend's apartment sometimes and the other two were who I spoke to as mutual friends) knowing I was at the apartment to try and intimidate me or something. 

After calling him out on all of it, things escalated and he got in my face. I'm not someone who throws the first punch but after he shoved me I socked him and he got floored. His other buddy tried to punch me and I picked him up and dropped him into the ground. Unfortunately, this is where it goes downhill. The first guy gets back up and puts me in a rear naked choke from behind as I'm beating up his friend. I look over to my left and the two mutual friends (who I thought would ultimately back me up not the other way around) are just watching in amusement. Great. After hearing all the noise, a few guys came out and broke it up. 

After all was said and done, we got reported to the disciplinary dean and despite myself claiming self-defense, we all got the same punishment. They had even lied about me starting the entire physical fight but there was a camera that showed the opposite. Still same punishment. Both guys were taller but "skinnier" than me so the dean actually had the audacity to claim it was a fair fight and I could've actually "really hurt them". We each (two guys in the fight and myself) had to write essays, be on disciplinary probation for the rest of my undergraduate, and go to an anger management class once a week for 12 weeks in order to graduate (this was the dumbest part of all). 

My girlfriend who saw the whole thing didn't defend me against the dean and these guys and actually told him I would've fought this guy if he ever started something with me (this is completely true but what kind of genius do you have to be to tell the dean that). She broke up with me a few weeks after that, just in time for my wonderfully useful anger management classes to start. 

This is probably one of my biggest dumb moments (read: fighting over a girl who wasn't worth it to begin with). The fight was something I think back on from time to time and get angry at myself about but the real regret was not dropping my ex sooner. Not long after that, I got a dream job at a top bank and she hasn't moved on from peaking in college. All said and done, she was probably my biggest internal motivation in college when it came to recruiting and landing the FT offer. I wanted to prove to myself that she made a huge mistake dumping me. Some of my biggest failures in life caused me my greatest rewards. Her dumping me ultimately gave me the motivation to work harder than ever before to succeed. 

TL;DR: I was a simp for a highschool girlfriend in college, got into a fight, was broken up with, motivated me more than anything else to become successful and achieve what I wanted.