How To Win Friends And Analyze Myself To Death

Disclaimer: I am possibly the most socially awkward person on the planet.

It's like reverse stage fright — put me under a spotlight in front of hundreds of people and I'll sing, dance, strip or tell jokes without shedding a drop of sweat. Sit me down across the table from a co-worker at lunch or let me loose at a party without a wingperson, however, and I suddenly become Rain Man. I flounder when it's one-on-one. It's embarrassing and crippling to practically every aspect of my existence, from my career prospects to my love life. I mean, first dates are hard enough to get through without a Greek chorus of hyper-critical mental patients screaming at you from inside your own head and rendering you essentially immobile, you know?

Luckily for you, loyal readers, I come off much more charming and witty in writing than I do in real life.

Um...right?

Anyway, I can basically boil it all down to one simple diagnosis: I don't know how to talk to people. Unless the occasion calls for an Eddie Izzard quote, I have no idea how to start conversations. Even simple ones. For example, the girl standing next to me on the subway is wearing the same shade of blue nail polish as me, and I can't even bring myself to say, "Hey, nice nail polish!" I rationalize this to myself by noting that she's listening to an iPod, and something so trivial is surely not worth interrupting her musical interlude. Then I think, well, I could still do the mime version (point to her nails/point to mine/thumbs-up), but I still don't because...uh...well, I have no idea, really. See?

Of course, there was the time I actually worked up the nerve to say something to that guy on the train with the saxophone case. What I said was: "Hey, is that a saxophone?"

"Why, yes it is," he says and smiles.

"Oh. Cool."

*facepalm*

So tonight on the way home from work, I notice that the boy with the Elvis Costello glasses sitting next to me is reading a book by Gregory Maguire, and it trips this train of thought: "Hey, Gregory Maguire — isn't that the guy who wrote Wicked? I wonder if this guy's read Wicked. Or seen the play. I liked the play. The book was too weird for me. I didn't even finish it, which is also weird for me. Maybe I would have liked it better if I hadn't seen the show first..." And suddenly it occurs to me, hey — this could be a conversation! And he's not wearing an iPod! Here's my opening! But wait — what if he's reading because he doesn't want to be disturbed?

I agonize over this conundrum all the way from Bleecker to DeKalb, at which point my potential bookworm friend exits the train and I cease agonizing and commence kicking myself for not taking advantage of the opportunity instead. Thus, the vicious cycle.

So, what I'm asking for, loyal readers, is your help. What am I doing wrong here? How do normal people talk to each other? Where is that fine line between "friendly stranger" and "annoying and/or creepy stranger" located? The future health of my social life, never mind the possibility of me ever getting laid again, may depend on your assistance. Please, find it in your heart to contribute to the cause. Thank you for your time.