However attractive, well dressed, confidant you are, you still need to know how to actually approach someone.

A problem is that any attempt to improve attractiveness will lead some people to declare that you are evil or otherwise defective. Its not just PUA stuff, this is far more general: if a guy lifts, that makes him a 'dickhead' according to members of my peer group, while a woman not shaving her armpits makes her strong & empowered (does a man not shaving his face make him empowered?). Conversely, some people believe that not taking care of your appearance makes you a slob.

Then there's the problem that confidence is key. You need to be 110% confident of everything you say, and to truly believe this, you need to internalise it. The problem is then that it spills over into other aspects of life, and you become very badly credence calibrated, potentially leading to serious mistakes because you can't admit that you might be wrong. When you are in a group containing more than one 'alpha male' it becomes impossible to get anything done, even something as simple as choosing a pub to go to, because one alpha male decides to go to one pub, the other decides to go to a different pub, and because they are alpha, they don't ask anyone else what they want, and so everyone ends up at a different pub.

In fact, its possible that LW rationality is training people to have bad social skills. "How to change your mind" might just be how to look like a weak-willed person who won't stick to their guns, or if you change your mind about politics, it makes you a traitor.

But if you have too little confidence, you can get stuck in a loop where:

low confidence -> little romantic success -> low confidence -> little romantic success ...