I've recently become a bit better about AA. I can fairly comfortably approach a woman, regardless of whether she looks busy or not (maybe she's listening to music or hammering her phone), and start talking to her.

I'll do a simple "Hey, how's it going", she'll usually respond with a skeptical "Hey.." and I'll follow up with a "What are you up to?", but it seems like most of the times I'll get a puzzled/weirded-out "Why are you talking to me?" face from them. A lot of the times the actual answer will be something like "Uh.. nothing?", and then the ball is back in my court. At this point I'll usually follow up with one-two basic questions (where are you from yada yada. / doing anything fun tonight..), but it feels like I'm really muscling my way through as opposed to this being more natural. In my experience, situational openers are a lot smoother (e.g. bitching about the bus being always late got me a # yesterday at a bus stop) and direct approaches (I thought you were cute, bla bla) at least polarize them a lot faster. Generally after a few cold responses I'll just drop it and move on.

Sometimes I'll go a bit meta and say something along the lines of "Isn't it amazing how people nowadays find it so odd to start a conversation with a stranger? Your expression shows you haven't talked to someone you don't know in ages!" and that seems to often break the ice a little, but I could probably do better.

Any thoughts on this based on your experience? Anything that makes the initial impact of being approached out of the blue a bit smoother? Smile and eye contact assumed, of course.