Internal Monologue Upon an Encounter With a Pretty Girl

Every once in a while, I'll have a moment when I have a chance encounter with a girl I don't know, a stranger who I come across completely randomly and unsolicited, who I happen to find attractive. It would be a situation where the two of us would be placed at a certain venue for a certain period of time simultaneously, as if by fate. Typical examples of this would be sharing an elevator, sitting across or even next to one another on the subway, or one in front of the other in line at Starbucks.

While I might be attracted to this girl, there is nothing for sure saying that this girl is attracted to me. Though I have been told by a few people that I am not a bad-looking fellow myself, I don't have high hopes. I like to think it is possible, though, that this girl might find me attractive in return. Besides, I think in general I have the kind of look about me that lets people know that I'm kind of always searching.

So I'm in this situation where I'm one-on-one with a girl who I might care to get to know a little further. A man with more finesse than I would gladly use this opportunity to lay down whatever his best line would be to get this girl to talk to him, while I tend to be more shy and reserved, and instead of thinking of something to say to this girl in our current situation that might catch her favor, I tend to just have a debate with myself in my mind.

I'm not an expert in picking up women, I do not claim to be, I never have. In fact, I can't really think of a time when I've done it successfully. I know that there are codes of conduct people use and there are certain signals women use to clue a guy in to invite him to talk to her. I have no idea what those are, and honestly I don't understand why it is the social standard for men to make the first move anyway. Evolutionarily speaking, women hold all the deciding factors on who gets to procreate the human race anyway, so why should I be forced to say something? I'm not going to waste my time if it's not going to work.

Something like that would be an excerpt of what I'm thinking as we quietly and separately ride along in the elevator or in the subway car or wait in line for our drinks. The rest would go something like this:
I wonder if she's thinking about me.
I wonder if she's thinking about my thinking about her. Do you think she knows that I'm thinking about her? Do you think she can sense it?

There is definitely some kind of awkwardness between us. I don't know if it is sexual tension or if it is just my own general awkwardness that is now being levitated between the two of us.

Does she find me attractive? Does she know that I find her attractive, and if so, how?

She keeps touching her hair. Does that mean something? She keeps looking out of the corner of her eye. Is she looking at me? Or is that just what I want to think that she's doing?

Does she realize that I'm staring at her? Oh! She's looking this way!
Quick!
Look somewhere else! Look up at that picture!

Oh, yes, that is an interesting picture. Sure, that's what I was thinking.

Well, my cover is surely blown, now. She can figure out what I think of her, so now I'm no different than any other pig of a man in this city.

I have always had the understanding that people don't want to be bothered, especially beautiful women. They already get the kind of attention they are sick of from all the guys who aren't afraid to say something. Probably all those guys from grade school and high school who just yelled out in the middle of class, those kinds of guys who were never afraid to just speak up, while I always raised my hand and waited to be called on. And it took me forever and a day to finally get a girlfriend. So, instead of saying something, I just continue to think:

I like her _____ (blank object: hair, hat, shoes, jacket, backpack. This is generally the case as there was something that drew my attention to her in the first place).
I wonder if I should tell her. If I did, would it do any good? Would it sound genuine? Or would it just sound like I'm trying to pick her up? Isn't that what I'm trying to do anyway?

I don't know. Don't ask me. I just came along for the ride.

Should I say something? This isn't going to last much longer. I've only got one shot at this realistically.

What if she does think of me highly and I don't say something to her? How will I ever know?
What if this whole time she's been waiting for me to say something to her? Maybe she's been teetering on the brink of a giggle just waiting for me to say something charming and sweep her off her feet.

Yeah, right!

But if she does think of me highly and I don't say something, is that going to hurt her feelings?
Is she going to walk away thinking she's not pretty?

She is pretty.

So now I'm responsible for this girl's self-esteem? How is that fair?!

Yeah, that's right, bitch! Take your coffee and walk away. I'm not saying nothing. I'm not gonna fight your battles for you.

See ya!

There she goes, the love of my life, right out the door. And now I'll never know.

Come back!

The worst is trying to accommodate this kind of situation at a bar, especially a loud one. I can be charming and flirt with the best of them, but I will never be any good at giving a line to a girl and having her instantly fall in love with me. I am hopeless that way. I need a third party to introduce us or to bring us together through some situation or some kind of common environment or common goal to use as a springboard. I can't just paint on a blank canvas. I need some kind of backdrop to work from.

I had a situation at a bar recently where I was talking to a girl who I wasn't the slightest bit attracted to, but it was apparent that she was into me. Our connection was music and so we got to talking about music-related things for a while. But it was very uncomfortable and awkward. We had to go back and forth yelling at each other, and I could only hear her half the time. The other half of the time I didn't know what she was talking about. She was way more into music than I am. And the fact that I wasn't interested in her wasn't helping at all.

HER: Do you want a drink?

ME: (Now that's what I'm talking about! This never happens!) Sure.

I even got an expensive one. Within reason.

HER: I'd really love to be a Broadway actress, but I know I don't have the body of a Broadway actress. I'm honest with myself.

ME: (It's true. She doesn't. It's nice that she can be honest with herself. But does this now obligate me to say something to the contrary so she doesn't go home and slit her wrists because she's not pretty ? Chivalry be damned!)...Well...I...wouldn't say you are unattractive. (Damnit! That is so vague and it sounds terrible! This isn't Austin Powers, Leland! You can't just say something with inflection and expect it to come out right!) ...What I mean to say is that I think you're very pretty. (That is such a lie! I am ashamed of myself. I am choking on my own guilt!)

HER (all smiles): Oh! Thank you!

ME: (I hope you're happy! I coughed up some very good beer!)

I've come to realize that some women are labeled unattainable by men because they are so stunningly gorgeous they know they could have any man, and therefore do not take any man, but instead go around teasing men and playing mind games to gain power and control in relationships.
Along the same lines, I think that I am unattainable, but not for any of these kinds of reasons, but in the fact that I'm so confused as to what's going on that I'll never get the chance to express myself correctly. Even if I did get the opportunity, my neurotic mentalities would probably get in the way of my success, as exhibited in the preceding statements. What woman could possibly want me, especially after everything I just admitted to?