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jkaufman comments on Ask and Guess - Less Wrong Discussion
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It would be disadvantageous to "be a guesser" in the sense of feeling obligated to guess instead of ask, but applying some guessing can be advantageous in an ask culture. By avoiding asking people questions when the answers would make them uncomfortable (no I don't want to pick you up at the airport, no you can't come to the party) you are more pleasant to be around.