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Why is it "guesser" rather than, say, "hinter"?

I guess it's because they expect others to operate at the same level so they will expect to guess what others want.

But I agree with you, it should switch to align from the perspective of the person wanting something.

I've also seen responses saying that the framing of "ask" culture makes it sound as though it's all "ask" and no "tell", which is counterproductive.