I think it really depends on the woman. Some people have little to no experience of self-doubt, despair or any kind of mental illness. Some others also don't but are open minded enough not to just dismiss you as crazy. Generally it's probably better to keep really personal stuff to yourself until you get to know the person and can gauge their reaction to any "weirdness"
And I mean that in the best possible way.
It's true that women like confidence in a man, but if you fake it for a couple minutes when you first meet her she will pretty much always have that impression of you. I know that can be almost impossible for somebody with SA but the only way to get a girl is to put yourself out there. I'm sorry if all my advice (and i use that term loosely) is sounding totally obvious, but I guess what I'm trying to say is that if you take a few risks - eventually you will get a payoff and that will boost your confidence 100%
You are young and you certainly write well and come of as an intelligent human being. Don't feel like you've missed out on anything, as you are just at the age where many women are looking for something more serious, and will overlook the extroverted fools they dated in their teens and early twenties for someone who will treat them well and be a partner to them. I guess I don't really know anything about you and so I don't really know what kind of women you are interested in, so sorry if this is all just off base and useless to you..
I met my current bf at a bus stop. We were checking each other out then he came up to me and was very direct. We've been together for just over a year and as I've gotten to know him better I've discovered that he's not as self-confident as I first assumed. He took a gamble cuz he.. liked the look of me and it payed off. I am way too scared to ever approach somebody I'm interested in, so most of the people I've been with have been VERY confident, extroverted types. My first shy boy is awesome though, he's not as introverted as me and he has to be quite outgoing for the kind of work he does - but he's definitely not the frat boy type
Sorry for the long post, just wanted to write you a quick note and it turned into a gd novel.
Take care..