I had the problem that my top result on Best Face is a) out of date, and visibly different from my current appearance, and b) a picture which I personally don't like, although friends have told me that they do. (It's the one with the brown scarf.) So I go back and forth on whether to use it or not.

ETA: Huh. As I look back through my reports, I notice that all my pictures other than that one also rate higher with women than with men--and the ratings of that picture vary significantly between one report and the other. (Also, I imagine the conference bike picture would have rated higher among geeks if they recognized the other people on the conference bike.)

By the way, I'm sure you know this already, but don't rely on being able to keep the painting up as your photo, as it violates site policy.