My shyness is a right bastard, can't talk to females much, and ones I'm attracted to not at all, so I consider myself very shy indeed in that regard.
BUT, messing with guys/friends/strangers on the internet I pretty much do a 180 and have no shame. Recent example of this is the goat edition songs, which caused me to scream like a fucktard at work whenever it fits to one of the songs on the radio.
I'm also pretty open about stuff like porn to whoever will listen. Or brag about really dumb shit I've done in the past, like trying to juggle crates at work despite not knowing how to juggle at all, not even with stuff that's meant to be juggled. So I promptly bashed my own face in on the first attempt, breaking teeth and causing a lot of blood to depart from their designated area.
And then I told fucking EVERYONE. Hell, I just told all of you.
I would really love it if even a fraction of this would come to me when I'm trying to chat with a lovely female, but it always fails me. And when I do manage to utter and stutter something it's always some generic shit that's worse than silence. "Some weather huh?". Weak shit that is, very weak.
Oh well, I'll get there one day.
Sorry OP, no advice here. I did have an experience similar to yours, when I was still going to school.
This cute blond gothy girl would be on the same train as me sometimes. I never even occurred to me to talk to her, but one day we were sitting across from eachother and I was listening to Stephen Lynch's Superhero on my ipod. I couldn't stop grinning through it, and when I glance her way I noticed she was smiling back at me.
If I could do any part of my life over, it'd probably be that one, and I would somehow find the balls to talk to her.
Yes, I'd pick that over bashing in my own face with a crate. Hell, I'd bash my face in 3 times over for a chance like that. It didn't even hurt all that bad, except for you know, eating... And breathing.
Best of luck to you OP, I hope it works out in a way that is satisfactory to you.
PS. To those that go; "Just talk to her, what's the worse that could happen?", the answer is 'losing hope'.
As long as we don't talk to her, there's always that chance, that slight possibility that, however improbable, if we did approach, she might say yes. Somehow we trick our selfs into thinking that that tiniest sliver of hope is better than getting shot down and moving on.
It is extremely stupid, I know.