TerriblySorry comments on How to signal curiosity? - Less Wrong
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Eliezer asked Abram a question out of curiosity, and Abram thought it might be a challenge or rhetorical technique.
Sometimes I ask questions that look rhetorical but aren't, and when I notice myself doing this I append something like "not a rhetorical question, I actually want to know" at the end.
How do you recognize when your question will be interpreted as rhetorical? ibid.
Experience? My main heuristic is something like "if I imagine someone saying this, do they have a smug look on their face?"