(Some) guys are told that their value as a man is tied to how good they are at "getting" women. So every conversation with a woman is framed in terms of an existential threat: if you're not getting enough women, you're not a real man.

Sorry, it was a very weird request.

We seriously need a social protocol for situations where A says something which makes B feel very sorry, but the proper recipients of B's apology are no longer available to hear it. It felt way too cheesy to just apologize to myself, so I apologized to you, but that doesn't make me feel any better about my womanizing and discriminatory past. Live and learn, I guess.