When in need of a conversation topic, ask a question about the other person's life. Anything about their life. (If I can't think of something else, I ask about weekend plans.) Listen for what part of their answer they're most interested in. Ask followup questions about that thing. Repeat as necessary.
People like to talk about themselves. This cuts awkward silences down to nothing and makes people like you. I've also learned all sorts of fascinating things about my acquaintances.
Do you have more examples of specific questions you like to ask? I've been trying to figure out a good way to get people to talk about the people in their lives (friends, family etc.), just cause I usually like to hear people talk about that.
Simple things I've asked are:
Do you have roommates?
But I'd like to figure out how to get people to tell me stories and descriptions of the people in their life.
This is an extension of a comment I made that I can't find and also a request for examples. It seems plausible that, when giving advice, many people optimize for deepness or punchiness of the advice rather than for actual practical value. There may be good reasons to do this - e.g. advice that sounds deep or punchy might be more likely to be listened to - but as a corollary, there could be valuable advice that people generally don't give because it doesn't sound deep or punchy. Let's call this boring advice.
An example that's been discussed on LW several times is "make checklists." Checklists are great. We should totally make checklists. But "make checklists" is not a deep or punchy thing to say. Other examples include "google things" and "exercise."
I would like people to use this thread to post other examples of boring advice. If you can, provide evidence and/or a plausible argument that your boring advice actually is useful, but I would prefer that you err on the side of boring but not necessarily useful in the name of more thoroughly searching a plausibly under-searched part of advicespace.
Upvotes on advice posted in this thread should be based on your estimate of the usefulness of the advice; in particular, please do not vote up advice just because it sounds deep or punchy.