to me the only in-universe explanation for george to be having so many dates with women is that these women (clearly needing to work on their insecurities) were going out with some total wall street jerks and george's repressed homosexual energy called to them like a foghorn in moments of desperation. happens in the contemporary dating scene too. imagine how george's dates were explaining him to their friends. "he's so agreeable and puts on some effort unlike those patrick bateman types, I just wanted to give him a chance, isn't he nice?". at least one friend was going "girl, he's in the closet"