Someone earlier said they think his issue was an extreme amount of self-hate, and my first impulse was to dismiss that idea. But in re-thinking it, it’s probably true that he loathed himself a lot. His hatred for others might have been his ego’s way of making sense of the feelings he felt towards himself.
It appears that he remained on the sidelines. He never approached women or attempted to make friends. Superficially, he expected them to initiate because he felt entitled due to his supreme awesomeness. But in considering this deeper, this sounds like an ego-sparing maneuver to me. Put forth as little effort as possible and you never have to endure outright rejection; passivity removes you from any responsibility and allows you to fault other people when things don’t go “right”.
If he’d had a girlfriend, I imagine he would have had nothing but contempt for her. “She’s just with me because of my car and money.” “She’s just with me because I conned her into thinking I’m a alpha male jerk.” There would be no winning with him.