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This is part of the reason why I have trouble talking to women. I get, for some ridiculous reason, absolutely terrified sometimes that if I talk about anything besides the business at hand or completely innocently casual material like the weather, that I will cross some sort of sexist boundary. I have no idea why this effects me this powerfully, as logically, I can see that this is completely insane - but it does. I never see it happening when it IS happening, so I can't stop it from happening.
I've always told my friends that I only insult them BECAUSE they're my friend. That messing with people is a sign of my love. It's true. I wouldn't have the courage to do it to anyone else. with me and my roommate (my best friend in this city at least) it's entirely true, to the degree where the jokes between us are always targeted to the emotional buttons we know will hurt the worst. He's the only person I'd trust to do that with, because we're close enough to know that it's acceptable.
Also related to this topic is why I refuse to even find women attractive if I'm not already pretty good friends with them. Because I know I wouldn't talk to them otherwise. If i've never talked to you before - then me finding you attractive is actually pretty much a turn-off for me. Because that just means I'll probably have to avoid you. I can think you're hot all I want, but, inside, I know I probably won't have the courage to talk to you, so I don't bother investing much into you.
This sometimes hilariously backfires, though, when such a girl I've resigned to this fate I later end up becoming friends with, after it turns out they're a friend of a friend or something, and I DO end up having to talk to them. Heh!