Shoulda Woulda Coulda

So as we’re leaving, I notice a rather attractive waitress. She was nowhere near our table this evening, but I get a glimpse of her as we’re putting on our coats. Immediately smitten. I thought briefly about going up to talk to her, but seeing how I was around all my workmates, that didn’t seem like the ideal time.

Odd. All the way out of the restaurant, I wanted to run back and just ask her out. And I was preoccupied with the thought for a long while, until my friend Justin dropped me off at home. Even then, I was tempted to hop into a cab and run back to the restaurant, just to see if she was still there.

But I didn’t.

And I’m beating myseful up for it right now. And I’m spiralling into the kind of incessant, mental loops that I’m so good at doing. Right now, I’m thinking less about this girl… and more about who I am, how I am. The idea of just approaching her in the restaurant seemed, well… gauche. And a bit creepy to. I’m sure a ton of men have done that kind of crap already.

Had I gone back and asked her out – would that have really been me? For every long-term, serious relationship I’ve been in… things have always started off as friends first. And I’m wondering why – is there less risk that way? Is it easier to begin with friendship, since the possibility for hurt may be lessened?

This is the kind of thing I’m talking about. What do most guys do? Do they just go up to people and say "Hi. Wanna go out?" I feel like I do a lot of overanalzying. Am I thinking things through too much? Do I need to just act and react more often, without preparation and planning and…

*looks at preceding paragraphs*

Strike that. I know I do.

Well, I guess it’s a positive thing that I seriously contemplated asking a complete stranger out, inaction aside. Maybe that’s my brain trying to tell me something. Tonight, I think I could feel the diving board between my toes – that cold, blue, grittiness. I can hear all of you, yelling, but I’m still just standing there.