When you truly reach a point of total apathy regarding how others see you—then nothing you do will be awkward.
Really, I probably could have posted just this sentence. Exactly what I meant.
At first, this attitude was difficult to achieve, and sort of forced - thus I'd go to the grocery store with messy hair, and have to force myself to remember "you're a robot!" Now, however, it doesn't even enter my head to worry.
Although one thing I still kind of struggle with is feelings about the opposite sex. I'm hoping to read more comments regarding it.
This is probably largely what spurred the "robot approach." In my all my favorite fantasy or sci-fi stories, there's always that episode or chapter where A Female seduces all the normal characters (unintentionally or otherwise)... but The Robot remains immune. It's almost like a superpower (in this context), to be unmoved by beauty.
In real life, of course, I have only rarely been approached by beautiful females intent upon seducing me in order to take over my spaceship. But I did often feel like they had undue power over me; so I'd think to myself "ha, ha; she thinks I have a crush on her because she's pretty and I'm not, but really all I care about is science!" (Though I did eventually meet a girl who had a thing for mad scientists. Took more than two decades, though.)
Also, I... uh... once pretended to be gay. Turns out females can be great friends if there's no sexual tension. This served as a valuable lesson to me; since most of the tension was evidently just in my head (girls don't actually seem to immediately assume I'm trying to get in their pants like I feared), if you just act unconcerned you'll probably find they have no problem hanging out with you.
(I just realized a lot of this is not directly relevant to your problem, but it's at least somewhat related, so I've posted it anyway.)
Surely it can't have been that bad for everyone, otherwise there'd be an outrage!
...
People never seem to talk about Boarding Schools as opposed to Normal Schools.... Nor do they compare it much wioth Homeschooling.
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.