Not specific to hacker culture, but I always felt there was a bit of a double standard when it comes to alpha male behavior. Women are attracted to aggressive men. Women like men who take charge. Women like men who are the initiators. Now obviously there is a line that crosses over into sexual harassment, but the fact is that men who behave aggressively are the ones who succeed in sexual pursuits most often. It's alm…
Yep, and that makes it incredibly hard to be a guy. You're almost "damned if you do, damned if you don't" when it comes to flirting and initiating things. Unfortunately, it's almost impossible to know - in advance - how someone is going to react.
That said, there is a line somewhere, of behavior that is never appropriate towards someone that you don't already have an established relationship with. Asking a random female (or male, for that matter) to "come up to my room for a pillowfight" is just stupid in almost every conceivable context.