I like to have a couple of these in my pocket so when I meet someone new I can ask something that hopefully yields an interesting answer. My go-to for years has been “what’s the worst advice you’ve ever received?”
-What’s a story your parents like to tell about you? (credit to Anshul Aggarwal for this. I have only heard this one in a formal interview setting, though).
-What’s the best book you’ve read that you disagree entirely with?
-Who did you worship when you were younger?
-Do you think the rate of technological progress has slowed over the last 50 years? (then you proceed to convince them that it has).
-What’s the worst decision you made that turned out well? (and vice-versa: best decision that went terribly)
-Do you know of any fun online blogs?
-What do you do to remain weird?
-What’s something only people from your hometown do?
-Why do you think people buy expensive things they don’t need?
-What’s something you take seriously?
-What’s your opinion of Los Angeles? (works in any locale)
-What’s the taboo thing to do in [insert person’s hobby]?
-What’s the weirdest joke you find funny?
-What do you think is the most underrated personality trait?
-I don’t think computer science is really a science. Do you? (only works for CS people).
-If you could write an op-ed for the NYTimes, what would it be about?
-Do you trust economists?
-What’s the best city that’s not your hometown?
