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Grothor comments on Stupid Questions August 2015 - Less Wrong
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Right! And this is why I tried to get her talking about fashion. I think your suggestion of asking more specific questions is very helpful. I'll definitely try that next time I'm having trouble with the more generic "tell me about your expertise" type questions.
Yeah. One more thing - in some ways I'm a bit egocentric. So my instinct is to think about the thoughts that I have on the topic and discuss them (I tend to have a lot of thoughts about a lot of things. Or at least a lot of questions.). I notice that I didn't think too much about the strategy of evoking her strongly held opinions. But something about my more egocentric approach of pursuing lines of conversation that interest me feels more... natural/genuine, which I think often leads to good.
(Not that I've had much success. I've always done well in "natural" conversations and am outgoing, but I've never been motivated enough to overcome the awkwardness of initiating conversations with random people out of nothing.)