How do I not be shy?

dear edahn,

there's this woman i see all the time. the thing is i'm a shy guy when it comes to approaching women, though i'd like to talk to her so very much. the other thing is, i'm not sure that i'm looking for a relationship with her but she has this intelligent, gentle look on her face, my 'instinct' just tells me i must get to know her, even if we just end up good friends. of course, i'm also afraid i'm gonna annoy the living lights out of her, but frankly i don't really give two pennies about that. what would you do in my place? do you approach a woman you like or you just wait for them to come to you, like me?

How do I put this gently...


You sound like a dork. 

Now, being a dork is no problem at all; my favorite people are all huge dorks. But they don't sound like dorks. You sound like a rich, uptight 50 year old British nobleman who sips brandy, wears a top hat and says Cheerio! too often. (Note: once = too often.) So first off, lose the formality. Tuck out your shirt, mess up your hair a little, and try and walk with some style. Right now, out loud, complete this sentence using the most ghastlyyy curse words you can think of. Ready? GO.

If Edahn wasn't such a _______, _______ _______, 
he probably wouldn't have to date _______, _______ _______ 
with _______ the size of _______ .

Good. Very good. Now, regarding this woman, you've got to just try talking to her. It doesn't matter what you say, just say something like "Hi, I think I've seen you here before. I'm Sir William Wellingtoncox," and smile. Hopefully you're not peeking through her bedroom window when you say it.

You don't have to look at this as your only opportunity to get her interested in you. You run into this woman a lot, right? So just look at this first conversation as a chance to say hello and show her that you're not a total creeper. That way, the next time you run into each other, you can say hello and she's already familiar with you because she'll recognize your top hat. The next conversation will feel much more natural and you won't be as nervous. And if for some reason it doesn't work out, well, that's okay. You stood up to your fears and that's a victory all by itself. Good luck, friend!

*Readers! Do this too! I'll start it off: If Edahn wasn't such a shit-eating, sloth-raping vomit bag, he wouldn't have to date moldy, disease-infested cock jugglers with nipples the size of dinner plates.