Ask HN: How do I get better at dinner conversations?
Recently, I invited my colleagues over for a farewell dinner and inadvertently put myself in the spot, by being asked a lot of inquisitive get-to-know-me better questions such as 1) Who among us did you feel turned out the most different from what you originally expected? 2) What are the top 5 things you'll miss about leaving this place? (Mountain View, if that helps) 3)What are the top 5 things you learnt over the course of the past year? etc.
I had either one-word responses or some very uninteresting answers and knew I was making the conversation stilted and boring. It was pretty awkward, and there came a point when I just wanted to be put out of the misery, and just be a fly in the wall, listening in on the fun conversation that the group would have, minus me.
So, to all the guys who make smalltalk seem effortless, how do you guys do it? Can this be learned? Should this be learned? It's very easy. Ask people about themselves, and follow up with more questions. Ask about things you are genuinely curious about. I've found in 95% of discussions this will do it, and perhaps the other 5% are not worth having.