I certainly agree with your suggestion that appearing to fit in to broadly accepted catagories probably makes it easier not to care how I'm being categorized. I think I've even made this point myself at times. The differentiation I was trying to convey (not very clearly, in retrospect), was between a) concern for repercussions, and b) intrinsically caring what people think. Also, to clarify, none of those points was intended as any sort of advice or suggestions. I was just relating my (probably irrelevant) experiences in tangentially related areas, in the lack of anything useful to say.

I've been thinking lately about individual cases and generalizations. It seems like there's some useful insight in there somewhere, but I haven't been able to put my finger on it. On the one hand, assuming things about a person based on generalizations is often going to be inaccurate, and could be construed as specifically offensive or hurtful. On the other hand, generalization can be a valid and useful tool when considering many subject matters - geology or what kinds of food you like to eat, for instance. I'm not sure exactly where the distinction lies. I think perhaps it's to do with seeing the generalized group as a single entity, and a willingness to revise assumptions, but like I said, I haven't been able to put my finger on it.