Firstly, wow, what a story. I think you mentioned too much, but I got the main gist of things. You've screwed up in light of this girl a good few times, and I think you should probably stop doing stupid shit that's landing you in situations were you can't even talk to her for months at a time.

Reading through the whole thing, I believe you actually like this girl. It's not a lust thing because she's "hot" or whatever. If it was, she'd be leading you on and you'd be dumb enough to be following her for a whole year. If you seriously like her, then I implore you, stop doing stupid shit like betting or writing stories about her. That's ****ing creepy and desperate. Oh, and stop "confiding" in everyone at work - if you trust Chris, then go for it, but keep Leon and everyone else out of it. Leon is a little kid who knows no better than playing kiss chase. You're causing gossip, and I Clair is this quiet/private/geek, I don't think she's appreciating the trouble you're causing.

If you want something to go further with her, then you have nothing to loose if you ask her out for dinner or to the movies. If she says no, she has every goddamn reason to say so, but she may yet still be interested. Or maybe, you know, try and be a FRIEND? Friends don't do what you've done to her.