Better find a not-so-cool chick that you really love and that really loves you, or a cool one that doesn't care about status.My experience: for the nerdy guy, the beta-male adherent to an intellectual or aesthetic passion, the biggest payoff is to be found through "contrarian investing." My last girlfriend is very, very odd and an extreme wallflower. She also turned out to be one of the most perceptive, moral, and sensible people I know. As a bonus, underneath her very tasteful and modest wardrobe she's also quite the dreamy waif. When we met, she was 25 and I was her first boyfriend.
Another anecdote: my sister living in New York met some guy and dated him for a couple of years. Not only did he turn out to be one of the nicest, level-headed guys I know, but he would be a good casting choice for Clark Kent. He had never had a girlfriend before. My sister met him when he was 27.
Another anecdote: my girlfriend's friend. She's a complete head-turner with excellent taste in clothes, but had never dated anyone until her mid 20's either.
Just as in tech, there are many whose decision-mechanism is to follow the herd. Their discernment is clouded by fear of being wrong and disconnected from true discernment. Be the one who hacks social reality for the unnoticed treasure.
(P.S. In response to the inevitable skepticism: there are lots of things in social reality that distort perceptions. Racism is still a pretty powerful one here in the states.)