Relsqui comments on Open Thread, September, 2010-- part 2 - Less Wrong
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And then what do you do if they say "no"? :)
Personally, I'm annoyed by people who say "you can ask me anything, go ahead" (especially in response to the "most private thing" prompt on OKC). It's a way of putting the burden of making conversation on the other person, instead of sharing it with them.