[kmoser]

You don't have to engage in small talk or chit-chat: just have a genuine conversation with the other person, and end it when it starts to get tedious. I don't see these conversations having to last more than 10 or 15 minutes; an hour would be a really long time, unless you're enjoying it.

Agreed, this is not always fun or easy, but it may help to approach it like a hacker would: given a seemingly impenetrable system (a stranger's personality), how do you find something in common to talk about?

How to begin the convo and guide it will depend largely on who you're talking to (complete stranger, acquaintance, etc.) but a good starting topic would be something simple like websites and/or something related to your area of expertise or interest. Pro tip: ask them what things they're interested in and see if you can find common ground.