I do I stop letting all my opportunities slip by?

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I've come to find that most my social difficulties come not from direct symptoms of autism, but from social anxiety. My anxiety is like a gate - when it's closed, it acts as a wall, but once someone opens the door I pass right through. I'm probably very socially awkward, but from experience I've that's far better than not engaging at all. I think were it intersects with autism is that if acceptability is ever ambiguous, anxiety and passivity wins every time. Even though I know statistically that it's better to take the shot, I just can't, I'm caught in my head thinking about acting rather than actually acting. Being stuck between two decisions and trying to work up that nerve just leads to standing around awkwardly and maybe staring, which runs counter-effective to doing the right thing. I know if I want to actually get anywhere in my life I need to get pass this, I can't just only take those relationships that people hand to me, but it's so hard.

So anyway, there is a young woman I've seen at a few social events in the CS program at my university who sets my aspie-dar on fire. Today I saw her just sitting by herself and looking around and I figured she must have been thinking the same things I think when in such a situation, waiting for someone else to come over and talk to her. She triggers this mother-hen instinct in me, I'm a graduate student and she's almost certainly a freshman, and I want to mentor her and ensure she has a better experience than I did. Then the doubts come in. I'm male, she's female, so what if it gets mistaken for hitting on her, or even worse I do start become interested in her in other ways? Also, what if I do something that embarrasses her, especially if she figures out why I took an interest in her? So I just stand there, looking at the refreshment table and pretending to be waiting for dinner while ruminating over what to do. The thing is, I had the perfect excuse, we had sat at the same table before at a previous event but were never introduced to each other, but I just never acted on it. Even if I was wrong in my assumptions, just introducing myself would have been harmless enough. Ironically, what ended up happening is that someone ended up inviting me to his table first, so my attempt to play the other role was foiled.

The rest of the evening went great. Once the gate is opened, I can hold a conversation fine, and I at least made some new acquaintances. I glanced over at her a table a few times, and some other people had swooped in. One of the people at her table was a professor, and I'm wondering if he's her father, as they kinda look similar and there was a guy there who I figured might be her brother. If that's the case, I don't think I have anything to worry about her as she would have a strong support system here. So there was nothing wrong with this particular interaction, it's just the lingering thought of what could have been if I acted differently or if things didn't unfold the way that it did. This will certainly not be the last time things will. I have empathy, I wish I could act on it better. I also need to be better for my own sake, I'd like to get married someday and that's not going to happen if I never date to anyone simply because I never talk to anyone outside of formal contexts.

I'm not sure how much of this would apply to you, but part of anxiety for me was looking for the "right" or "perfect" response, which really doesn't exist. Having to perform socially and having something to prove. So it creates an impasse that inevitably results in withdrawing because nothing lives up to that idea of how the perfect or ideal social interaction will go. People are unpredictable. In many cases which of two choices you make for what to say doesn't matter that much, barring the majorly rude.