So like easy example - you see someone you're acquainted with and say something like "hey how's it going?" They'll say something like "good man how are you?" And you say "good." Conversation goes nowhere. That's been me for a long time.

Instead, say something like "hey man how've you been what have you been up to lately?" Now you've given them an opportunity to say hi and actually tell you something. They may still answer shortly but they will probably give you enough to follow up. Example, "oh not much man, just hanging with the wife and kids, the usual." But there - you have some things to dip into. 1) oh nice you guys got any trips planned? 2) what are the kids into these days, they like that (thing kids are into) that's all the rage these days, or even 3) oh man how old is (kid) now?

I'm still not great at it but I'm much better at it than I used to be and trying to improve all the time.