He told me about his ex-girlfriend who had cheated on him, and then told him just to hurt him. I found out later that she had "let him down" by spending her birthday with her family instead of him, and despite having told her that he was okay with it he then ceased all contact for 3 weeks, ignoring all calls, emails, even her showing up at the door in person. During this time, she had turned to a friend, and ended up sleeping with him. When he finally made contact again, fully expecting her to still be his girlfriend and everything being rosy, she straight up told him that they were no longer together. When he ignored that she told him about the friend.
He spoke of his father as an abusive asshole who never gave him anything despite being rich. "Never giving anything" apparently equals refusing to buy him a new macbook after he trashed his 6 month old macbook retina over a game. He also didn't get a 13th iphone that year.
He broke up with his girlfriend because she was unsupportive and not prioritizing him enough. He had spent exam period smoking weed, gaming and partying, and had unsurprisingly failed every topic. The girlfriend spent her time studying, and passed. Biggest issue here was apparently that she refused to skip her last exam to comfort him over failing.
Went to the dean to complain about discrimination after he failed his exam. Found it unfair that he failed based on a single question. This was molecular cell biology and he couldn't answer what RNA was.
Talking to me about SAT scores and the old system vs. the new system. Said the system had gradually changed over time, and that SAT scores therefor aren't comparable at all. I told him I had read about it recently, told him how it had changed and when it had changed. He said there was no way I could know that. I looked it up, and showed it to him. He claimed to still be right. I said it wasn't possible for both of those scenarios to be correct, at which point he flipped his shit, said that I "always had to be right", claimed my disagreeing with him was a direct attack on him aaand didn't speak to me for weeks.
etc.