Stupidest thing I ever did was stand up to a bully in high-school. The starfish used to give everyone stuff, including my girlfriend. He also dealt drugs. On the day it happened, I was at my locker, and he pushed my head into it, drawing blood. I grabbed him by the shoulder, and landed a straight punch to his face, and then again from the left. I broke his nose, and he lost a tooth.
I ended up getting expelled from that school, but it was Term 3 of my last year, and me and my girlfriend go to the same university now.
He deserved it, but that moment has always had a dramatic impact on my life since then. (It came up in my job interview!) so I guess it was pretty stupid.
TL;DR
Punched a guy in the face and got expelled. He was raped in the city in the same day.