One thing that helped raise my confidence level and made many of these problems magically disappear is resistance training.
I'll just quote RAW on that:
Whenever you meet a young male or female, ask yourself consciously, 'If it came to hand-to-hand combat, could I beat him/her?' Then try to determine how much of your behavior is based on unconsciously asking and answering that question via pre-verbal 'body language'.
It didn't take much to get good results. After I put on 10kg (75->85 at 185cm) and got strong enough to actually do some push-ups, most people didn't feel threatening anymore.
(Well, and probably knowing that almost everybody will avoid fights at all costs, so you could do lots of damage even if you're a skinny nerd, but just are willing to actually attack. But only knowing this alone didn't do it, I actually had to gain some strength. I don't intend to ever actually get into a fight, but I run on hardware that cares about this crap.)
I'm 4'11" and not athletic. I occurred to me that if I was afraid of people for being bigger than me, I'd go around being afraid of people all the time, so I pretty much shut off that part of my mind off. I grant that this is presumably easier because I haven't be subject to much physical assault.
So far, this policy hasn't made my life any worse.
So I was there being my rationalist-with-akrasia-issues, nerdy, awkward self who studies acting, singing, rhetorics, PUA, TV Tropes, Machiavelli, The Art of War, the 48 Laws of Power, the Art of Seduction, the Seven Habits... in the hopes of escaping his chronic fear of his neighbor (with some success, shall I add, but it comes slowly). And then I sumble upon this nice little harmless meme:
Socially Awkward Penguin
I was absolutely stunned. This behavior. I thought it was strange and unique. It's incredibly common. This gave me great hope. If it is common, it means it isn't due to noise: there's a pattern there, there's something to unravel. The misjudgements of power, of what it's right to do, of when to fear and when to be bold, when to speak and when to be silent... What *is* the right thing to do when you're with a coworker on an elevator? What do you say when someone remembers you, but you don't remember them, and they have noticed that? What do you do when you're hit by a paper ball in class? What do you do when the only people you seem to be able to make friends with are older, younger, or of the opposite gender, and you're utterly intimidated by people of your same age and gender, the friendship of whom you know would profit you most? Why do you automatically recalculate trajectories to avoid acquaintances in the hall, at the super, on the bus? Why is it that when a person of the opposite gender so much as pays attention to you, you think you have a crush on them?
There are clues to some of these questions in the books and works I linked back there. But, more often than not, we expect those problems to solve themselves, with one magical word, "confidence".
I am confused at that notion. I find it unsatisfactory. I want to understand social awkwardness. The rules thereof. And how to vanquish it. And I want the keys in a way that can be taught. So that, when I have kids, they don't have to go through the same stupid struggles and can actually feel good about themselves and focus on getting stuff done.
So, I hereby summon the powers of the Lesswrong community: let us pick apart this problem as we know so well, and let us unbury the roots of this evil that is social awkwardness, so that we nerds and geeks may defeat it at last, and live free of its funk.