Dude, with friends like you guys, I'm surprised Simon didn't bail on you decades ago. Seriously, guys who act obnoxious around girls when they are in their late teens are nervous around women. Being in the "friend zone" enables them to get comfortable with a girl who might also be nervous about such things so things can develop naturally. But you all kept swooping in on that. Then, you obsess about his sexual activity, as if that is what makes a man (it isn't). You kept pressuring him about it, asking about it. And you keep setting him to have sex in a public way, as if it were a group effort, with sex workers with the rest of you being a cheering section. Just thinking about having sex in a bedroom in a crowded apartment with everyone outside the bedroom door focused on what happening would kill desire in most real men.
Simon shouldn't have resented women; he should have resented all of you. Seriously, dude, I'm surprised he didn't run from your group when he was in his early twenties.