Awkward

Why, oh, why is it so awkward to run into co-workers on the train? Especially when you're far from your destination? And you don't know the co-worker that well? Now, these questions may all seem rhetorical but believe me, THEY ARE NOT. On the Jay St. – Borough Hall platform, I ran into Roland, who heads up the interactive division here at US Concepts. I don't know him that well, but he's always seemed like a nice enough. But man, oh, MAN, it was strange riding to work with him. Because, you know, once you acknowledge that you're on the same train, you have stand next to each other or else you're being deliberately anti-social - and then you have to make some sort of conversation because it's kinda understood that conversation should trump reading, if you're with somebody you know. So what happened was the following exchange:

Roland: Hi.
Stefan: Hey! I didn't know we were on the same train. Where do you live?
Roland: Park Slope.
Stefan: Oh, me too. Where?
Roland: 5th St. & 4th Ave. By the gas station.
Stefan: The Hess?
Roland: No, the BP.
Stefan: Oh.
Pause.
Stefan: How long have you been in the Slope?
Roland: Three and a half years.
Pause.
Roland: How long did that meeting go yesterday?
Stefan: I don't know, I eventually grabbed one of those organic donuts and snuck out. Those donuts were aweseome.
Reaaaaaallllyy long pause during which Roland stares in the other direction and I start to read my magazine.

Now, granted, I'm not the best at small talk, but I'm enthusiastic and friendly (I think). I think it's Roland's fault, personally. Luckily, some ice was broken later when the subway we were in had some doors that wouldn't close, so we all had to exit. Complaining breeds solidarity, fortunately, and some funny griping ensued briefly. Then Roland led us onto the wrong train (heading towards Brooklyn instead of Manhattan), more funny griping ensued, and we managed to make it onto the right train and to our stop without much incident. More forced conversation upon exiting the train station about what we're both working on at the moment. Sigh. I just hate small talk. I'm not really good at it, and I can't really paper over gaps in conversation very well. It's one of the things I just wish I was better at. Mostly, I don't know what to ask people – I sorta run out of interesting questions to tease out their topics on interest. I have the basic New York questions down (where do you work, where do you live, where are you originally from, how much money do you make, that kind of thing) but beyond that, I'm just crap. It's my curse that I can be a very good friend to you if you've known me for about a month or so. But it's tough to get to that point if I just awkwardly stall out of every initial conversation. Anybody have any tips for me?