Alexei comments on "Stupid" questions thread - Less Wrong Discussion
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One of the most simple lessons that I got a lot of milage out of is: don't be afraid to state the obvious. A lot of conversations and human interactions are more about the positive vibe that's being created than about the content. (Somewhat less so in these circles.)
This is good advice for continuing an existing interaction with people, which I already feel like I'm pretty good at, but what I'm not so good at is starting such interactions with people I don't already know.