I and my (now) wife got him his girlfriend, his first girlfriend in 6+ years, by painstakingly convincing him to leave work early and come hang out with all of us, and the only way he ever attempted to impress her was by directly insulting me. (Technically he did have a girlfriend before the one I got him, but she was 16 when he was 24, she was morbidly obese, and she was extremely immature; Frankly, it was disgusting, but both his parents and her parents knew about and condoned the relationship)
He agreed to move out with me when I found a new job, which was a major reason I decided to take the job, (it wasn't practical with no roommate) but then forced me to live with his parents for almost a full year and literally cried several times when I brought up moving out.
He was a disgusting slob who would leave all of my dishes in his room, dirty, and then have the nerve to throw a fit when I entered his room to retrieve and clean them.
He brought multiple cats into my apartment and wouldn't clean up after or feed them unless I explicitly yelled at him for not cleaning up after his animals, and even then he would do his job that day and then immediately go back to not doing it. He actually left a full litter-box in his room for an entire year out of laziness - instead of cleaning it he just throw towels and clothes over it so the smell wouldn't seep through.
He was completely incapable of realizing that he could be in the wrong. Even when it was obvious, he would just be childish and passive-aggressive. I saw him write off several friends before we stopped talking, based on ridiculous shit, like them having a different perspective on life.
The list goes on.