I've been trying to come up with some interesting prompts after observing just asking someone "What's been happening" yields nothing but "Oh not much, work". So far the old classics of just probing in to what they do for work, what they did last weekend, etc and then finding any bit of info to drill down in to more interesting topics works best.
Also very important to recognize most conversation starters are someone serving the ball to you, you need to hit it back with a continuation. If you're giving one word dead end answers you've just caught the ball and dropped it.
I was a bit surprised to read this. I didn't think I'd stand out in the sea of comments here. But to this, since a couple of years ago I had a break up, moved city, quit all social media and went outside to real events. HN is the only place I still comment on.
Also very important to recognize most conversation starters are someone serving the ball to you, you need to hit it back with a continuation. If you're giving one word dead end answers you've just caught the ball and dropped it.