Poor guy.

This weekend I took myself to an alumni football-watching gathering at a bar in the city.  I was quite proud of myself, since I had gone alone and knew the place would be packed with nowhere to sit, which would force myself into social situations with others (namely, men).  And indeed, the game had just barely begun when a gentleman turned an eye toward me and introduced himself.

I am admittedly not very good at casual conversation with people I don't know.  I find small talk boring and feel like it's the same stale conversation every time.  However, I have had conversations with some folks I just met and could tell that I instantly clicked with them--something in the way the conversation flowed, was interesting, and took a few unexpected turns.  So I know it's possible to connect with someone right away.

I give him credit for doing all the right things.  He asked me what I do for work, what I do for fun, talked about the game we were watching, etc. etc.  All the typical small talk things.  But by the time half time rolled around, there had been enough awkward pause to fill the humane society (eh? get it?), and I found myself wondering if I would have to put up with this for the entire game (FWIW, the duration of a football game is a long time to keep up awkward small talk).  So even though at the beginning of the game, I thought, "this guy is kind of cute--as long as he's not a complete asshole, I'd give him my number," by halftime I was thinking, "wow, it would be really nice if I could talk to some of the other cute guys here...."  

Example of some of our odd conversation:
Him:  I like to go to concerts.
Me:  Yeah?  What was the last concert you went to?
Him:  I went to see the Cure at Madison Square Garden.
Me:  Oh wow, are they still touring?
Him:  No.  Well, I don't think so.  That was a long time ago.
Me: (thinking) are you sure you like to go to concerts.....?
 
I was also pretty claustrophobic at that point (I don't even know how the servers maneuvered around that place--I was pinned to the wall).  So I told him it was nice to meet him, and left.

Yeah, maybe I missed an opportunity, but he should have asked for my number sooner!  Close the deal!  Sure, I was moderately interested at first, but I was annoyed that I was stuck talking to him when I could have been talking to all sorts of people!  Not a good idea to wait until I'm bored.  As I walked away from the bar, I considered the situation.  What should I have done differently?  What should he have done?  Did he do all the right things?  What are your expectations for the pickup song and dance?

Trying to stay positive,
Skeptic