What was your most “Oh my God I seriously fucked up” moment?

For me, it was definitely confessing to my grade school rival (and bully) after I developed an interest in him due to the “drastic hormonal changes” I underwent during my highschool years. God, that relationship was really doomed to fall apart in less than a month. He was a walking red flag, and above all, the largest piece of shit I’d ever gotten the displeasure of meeting and dating. Egotistical, homophobic, racist, you name it. The shit stain also had a horrible sense of humor, and if that wasn’t enough he also looked like a hammerhead shark that had endless rows of uneven teeth...Lord forgive me for I have sinned.