Wait it out or not?

Like a good bunch of people here, I’ve had a crush on a girl I’ve been friends with for years but have been too painfully shy to say anything. A few months ago, after seeing her again and saying nothing, I decided I was going to do something about it. First I tried writing her a letter, but that never felt right. That’s when it hit me: why not just look her in the eye next time and ask her out? It felt like my older self slapping me across the head saying ‘go after her, stupid’. I had spent a lifetime being afraid of such a moment, but all of a sudden I was ready to face it. In fact, I began to want it so badly that it transcended her answer. No more waiting for her emails and taking it as a sign she doesn’t like me, no more walking on eggshells when I’m in her presence. Just me doing what I should have done years ago and letting go. At worst, it’ll hurt but I’ll be a much better person for it. At best, I get a date.

Well, easier said then done apparently. Now that I’m ready to face her, we can’t seem to get together! She’s cancelled on me twice and I’m not sure when she can reschedule. Now I feel I’m right back where I started, trying to get in touch with her, waiting for her to get back me and wondering if she ever will, only everything is intensified because I felt so close to finally letting my emotions out only to be denied the opportunity…twice. It’s not her fault of course and I doubt she even knows what I’m up to, but it doesn’t stop the pain I keep feeling and it’s making me feel worse. So now I’m torn with returning to that letter. What felt like a cowards way out is suddenly a way of taking matters into my own hands and what was supposed to be a step in confronting my fears is something I would have to wait for, while time keeps ticking away. Chances are I will be able to see her again if I just be patient. But I still feel my window closing and I desperately need to take this chance. I just want to be sure the best of me comes out when I do. In my mind, having the courage to ask her out in person is the highest compliment I can give her, no matter how heartfelt a letter I compose. But who knows if she’ll recognize that, maybe the point is to just let it out any way you can.

Hope I haven’t gone on too long. I’m going to make a decision soon, but if you can offer any advice in the meantime, I’d appreciate it.

No, no letter. You've chosen a different road- keep going that way.

Insist. Show up at her work five minutes before she gets off with a picnic basket. Make it happen.

I would if I could--but I don't know where she works. I DO have her phone number but calling feels cold to me. Ironically at this point I feel more confident if I were standing in front of her then hiding behind a phone. If I didn't know her as well, it'd be the opposite I suppose but I can't imagine going from being her friend to sounding like I just met her in a bar the night before. Plus if it goes to VM then I'm in the same boat---waiting for a call instead of an email.

Then again, maybe it's the better option compared to a letter.