Perhaps a distinction should be made between the different reasons for asking someone out, because there's a gender imbalance in them. Namely, one could desire someone mainly for sex (because the target is one of several attractive people around) or mainly because they want a relationship with that specific person (and none other), i.e. a crush. At least what I get from SSC's account of Aaronson's experience was that the latter was more motivated by sex. If lonely male nerds are motivated by the first and lonely female nerds (or girls in general) are motivated by the second, and both parties know this, then obviously the guy is going to be rejected. Both the guy and the girl need to have significantly more sexual experience than the typical high schooler in order for the idea of casual sex / friends with benefits to appeal to the girl. (Otherwise, the sex is probably going to suck for her in every way possible, from the burden of contraception to failure of the inexperienced boy to please her sexually.) If both guy and girl were to be looking for a mainly romantic partner (in a relationship that would obviously include sex, if at a later date), then the guy's chances for approaching her would go up. (That is not to say that they would go up by much above 0 in the given context. Expressing ("that kind of") interest in someone you're not on a chatting basis with, which apparently is how many nerdy guys approach the situation, with is a horrible social move that only the most charming and attractive can pull off. Flirting precedes confessions, people.)

I had zero experience with women in high school, but found I was well ahead of the curve after college. My experience is most single people under 30 have relationship issues to some degree or another. I find just generally being more socialable is the best cure. Trying to specifically get good at relationships without learning the rest of it is setting yourself up for failure.