As someone who was raised a girl, yes. Immediate red flags. Sets off all the misogyny radars. Any man who complains about feminists is going to be a bad time. Couple that with bragging about money and looks because he thinks that's what women want, yet still assuming women are shallow gold diggers even when he can't get a date despite being wealthy and attractive. The whole thing drips with passive-aggressive resentment. Why would anyone want to be around that?