Who is the worst person you have been forced to work or hang out with?

My ex-best friend. I successfully de-friended him in real life despite the fact that we grew up as kids and knew each other for about 20 years. His problem was plain and simple - he was sociopathic. I felt terrible for abandoning him because the only thing he genuinely seemed to care about in some form or another was his friendship with me. However, eventually his behavior became quite scary and I had to do something, so I cut ties. The shit he used to do ranged from pretty hilarious to downright scummy.

• He was exceptionally good with women and had a lot of sex - but one day when a girl told him that she’d “had bigger before”, he left and kicked in a window while wearing sandals. I took off my t-shirt and wrapped it around his foot to stop the gushing blood. Took him to the hospital, paid his $500 bill because he was broke. I still haven’t seen that money back. • One time while staying at my friend’s place he brought a traffic cone in from the street and left it in the living room. Then he went into one of the girl’s rooms, took panties from her drawer, opened the tub of butter in the fridge, put the panties in, closed the lid and left it there for her to find the next morning. • Stole hundreds of dollars from his little brother's college savings • When we were kids he took a shit and put it on my head while I was sleeping. He would also sometimes dangle spit from his mouth onto my face while I slept. • Got in numerous traffic accidents drunk driving, and got in trouble with the law to the point that he had to flee the country. • Borrowed hundreds of dollars from me and the only reason I got it back was because I threatened to stop hanging out with him (this money excludes the hospital bill btw). • Got fired from several jobs for being abusive and not reacting well to discipline. • Threatened to hit me a few times. Never actually did, but I wouldn't put it past him. He got in fights constantly. • The breaking point for me was when I invited him out for my friend's birthday the night before he was due to fly abroad. He spent the whole night picking physical fights with strangers and ended the night trying to hit on her. He ended up in tears after she called him a useless scumbag, and that no one gave a shit about him, and that fleeing the country wouldn't make him less of a fuck up. He cried and cried and I actually felt bad. The next morning I was having sex with my boyfriend when he walked right into our room, pretending to not know what we were doing. He apologized and immediately left. 30 mins later he knocked on the door, I let him in, and he asked to borrow $200 from me because he had lost it the night before. I refused. He pleaded with me and said he needed it for a cab to the airport or he'd miss his flight. I said that wasn't my problem. His response, "I guess I can just get the cab anyway and make a run for it when I get there."

So yeah... I'm done with him, and it's quite sad because when he was a cool guy he was a cool guy.

/r/AskReddit Thread