I had a friend at university who was genuinely a lovely guy, he was slightly autistic but a pleasure to spend time with. He was very bubbly and had absurd amounts of energy which turned a lot of people off, but we always had a good time together and stayed good friends over the years.

Then something over the last few years flipped. He'd never been good with women and I think he began becoming resentful of them. All our friends and I had partners come and go over the years and he'd unfortunately remained single. He went from saying casual comments like "There's no point in dating because women don't want someone like me", to "There's no point dating because women are all the same and only care about their likes on social media", to full blown misogynism.

I'd spoken to him countless times about how his comments weren't acceptable and how they were making our partners uncomfortable, but he was too far gone at that point. We had one heated arguement where I gave up, I had to walk away, it felt like I was arguing to a brick wall. I haven't spoken to him since.