He's not usually so insensitive, but when I pointed out his using "pussy" in such a derogatory way, he responded with "And that's another reason why no one likes me and I'm a major dickhole".

Pointing it out, I didn't say anything even remotely close to what he took away from it. And thus, my reluctance to call folks out on it.

sighs.

tangent: it's weird that we use words for sexual acts or organs as expletives or pejoratives

is that universal across cultures?

Sounds like disingenuous self-deprecation to me. IMO, he's playing games with you. Either you respond with, "No you're not! You're a good person!" and justify his misogyny alongside any other shitty behavior he

has, or you respond with something validating that he's a bad person and correspondingly become a bad person for putting him down.

more to the point: you're not responsible for his deal

to build on wakko's point. It doesn't matter what you say: you can only express what you're feeling and seeing - if you're calling out something observed that has a specific impact on you, that's unassailable

his reaction isn't in your control or purview.

though you could probably remove that as a reasonable scenario. "I know you're not a bad person and I still like you, but this action has this consequence"

You can also remind him that people generally will react to him based on the positive or negative content of his behavior. If he's experiencing lots of people treating him negatively, he should reflect on how

he is behaving and what he's doing to generate that reaction.

Or, to crib a great lne from a fantastic show, "If you meet an asshole in the morning, you met an asshole. If you meet assholes all day, you're the asshole."

I love that

alternately just kick him in the balls when he says shit like that. Because goddamn. Shut the fuck up.

I like that!