Someone asked, and I thought about it for a while: what makes a comment really mean? Context counts: strangers can say cruel stuff that should roll off, because you can’t take everything said by a random asshole seriously—especially on the Internet. Accuracy should count too: people who say mean but obviously false things can be laughed off, so mean things probably need to have enough truth to sting; they could be untrue but the sort of thing you’re worried about being true. Especially from people who know you well. Power dynamics might count too: a nasty comment from a boss or advisor might count for more than one from a peer.
With those parameters in mind, when I was an undergrad I was hanging out a party and this girl who was, uh, not conventionally attractive, began doing a mock strip-tease (I think / hope it was “mock,” anyway). One or two guys offered her dollar bills, and then she came over to me, and I said, extremely loudly, that I’d only pay her to keep her clothes on. The other guys laughed, but she looked like I’d just murdered her puppy.
I was mostly being funny. But women are used to being pursued and having sexual power over men; when they don’t, and when they have their lack of sexual power pointed directly observed, they become extremely upset in a way that I suspect most guys are used to (this is part of Norah Vincent’s point in the fourth chapter of Self-Made Man). This was around the same time I realized that being inured to a woman’s attractiveness yields the paradoxical-seeming result of being more successful with women. And I was realizing how many women are susceptible to status plays in sexual marketplace value, especially if they’re worried that theirs is low. An astonishing large number are. The mean thing is using this kind of status play on someone who isn’t conventionally attractive.