The iPod and social anxiety
I just left my job the other day and was waiting for the subway. There were about 15 people or so waiting and I noticed this one girl sitting on a bench. I slyly try to check her out. She’s pretty good looking.
The train arrives and I take a seat relatively close to her. I was going through my head trying to think of a possible way to try and start up a conversation. I noticed that she took a little memo book out of her purse and started writing. From what I could tell, she was writing about her observations of people on the train. But then my interest really peeked, because she was writing in a memo book that looked exactly like mine.
I usually keep mine for random thoughts, ideas, and whatever I feel I need to jot down.
It sounds lame to get excited about something like this, but the whole situation seemed too interesting to let go. I was about to shut off my iPod to try and go for it, but then I noticed she was listening to her iPod too. I didn’t notice because she had her hood up.
I wasn’t sure how to proceed.
So I did nothing.
Nothing.
Nothing.
I got off at my stop, and surprisingly, she got off at the same one.
We were both heading in the same direction and I followed her for a block. But then she went in a different direction.
I did nothing.
Nothing.
Nothing.
A cold approach is hard enough, and she probably did not want to be bothered. I probably wouldn’t have succeeded in maintaining a conversation, never mind getting her number. Maybe I wouldn’t have even liked her if I stared talking to her. But nothing makes it harder than when somebody is listening to an iPod.
How do you break that barrier? There aren’t any social rules for this yet. I could just try to talk over that, and then I would have to repeat whatever dumb conversation started I could think of. I could have also just kept trying to make eye contact with her and smile, something that is also difficult in our culture.
This is hardly a new topic to blog about, but I feel like I really missed an opportunity here. It pains me sometimes to add another “what if” to the master “what if” list. I just hope that I take the risk the next time an opportunity comes.
Edit: Violent Acres has something interesting to say on this situation. Maybe it was a good idea I didn’t say anything, but then again, most people aren’t as wonderfully bitchy as she is.

What was the risk to you if you politely interrupted her and asked her for her phone number?
Imagine if you got her attention and said something like…
“Excuse me; I’m sorry to interrupt you — I noticed that you were listening to your iPod, but I thought you looked like an interesting person that I’d like to get to know. Can I give you my number?”
Then she either says, “Sure” or “F— off.”
What’s the risk to you?
I don’t think I would have wanted to be interrupted, especially from some random guy on the subway. I know I wouldn’t want to be, unless she was hot. Consensus seems to say: headphones in - rest of the world, don’t bother me. I’ll limit to making a fool of myself to chicks who aren’t wearing headphones.