The possibility of a connection between romance and difficulty understanding women has been mentioned. I’m a bisexual woman, and I don’t have any problem identifying with or understanding men. I often find women somewhat more difficult. I think this is because I’m much more attracted to women, which makes them much more difficult to approach and raises the stakes somewhat.
Incidentally, I was rather surprised that there are so few women on Less Wrong. It hadn’t occurred to me that this would be the case.
I think we may be in the midst of such circumstances right now, actually. I’d be interested to know how much the LGBT rights movement is influencing gender roles, particularly male gender roles. The movement encourages people in general to question gender roles. Acceptance of transpeople, for instance, requires that people rethink the idea that gender and sex are equivalent.
Also, I think it’s interesting that gay men (or some of them, in any case), who belong to an oppressed subset of the power group, have been able to push gender boundaries to a great extent. This may have to do with the fact that traditional male gender roles dictate attraction to women, so gay men are already questioning their roles. I wonder, though, if the fact that they’re a subset of the power group will allow the movement to benefit all men.