Sack up and ask her out, instead of being an awkward 30 year old playing high-school level games with a girl. Worst case is that she says no, which puts you right where you are now.
Why people build this up to the point where they have to fall deeply in love from afar (or stalking, as normal people call it) before they can ask a girl out is beyond me. If you're interested, talk to her, hang out with her. She'll either be interested or not, but you'll know and can move forward accordingly. Stop building a chick flick romance novel in your head, and just talk to her. She probably won't bite (and even if they do, it's not the end of the world, it happens...)
And for God's sake, stop using your previous relationship as a crutch. If it was a recent thing, I'd understand, but it was a fairly BRIEF relationship, and it was almost a decade ago. Seriously dude, you're just using it as an excuse to wuss out and bitch about life. If you can't even man up enough to risk rejection, what's this girl supposed to be interested IN, and what part of a relationship with that kind of person would she be looking forward to?
First of all, you've no idea how much my previous relationship still hurts. She was someone I was deeply in love with and wanted to spend the rest of my life with. The karmatic "magic" of our "history" together is something that cannot be duplicated. She was, and I don't say this lightly, my soul mate. And she ripped my heart out and threw it in my face. I
still have feelings for her and I still miss her. Yeah, I'm mostly over it but it's still something that had a huge impact on me. There are still times it hurts, there are still times I wish, and even my own subconcious sees it fit to give me the occasional dream about her.
It was much more than a "brief" relationship ( and I don't see how dating for two years after knowing eachother and being friends for five before that could be considered "brief".)
Secondly, I'm already fully aware of my various emotional disabilites and quirks, they're all something that've plagued me since I was in grade school. I've always had trouble around people in general.
This isn't a simple matter of "I'm 30 years old, she's 25, I should just go over there and do it," I physically can't. It took all my will power to ask-out to previous girls and neither worked out (one due to my suckiness, one due to her already being in a relationship.)
I've got problems, I've always had these problems, and they're hard to overcome. I know I've got much to offer a woman, I've many good friendships with people so I'm obviously able to connect with people and maintain relationships and even aquiring those
male friendships took every ounce of my being.
That's what was so great about my previous relationship, it just... happened. It litteraly fell in my lap, no question on motive, it just happened out of passion and moment and spark. It's was, in a cliche, magical. Unfotuantly, she was too young, it was a (semi) long-distance relationship and I was going through alot of stresses and emotional troubles at the time (and a yet to be treated mental illness) and all of that was too much of a strain on things.
This isn't playing high-school games, this is the way I am, the way I am wired, and maybe even a little bit of God kicking me in the nuts because He hates me.