TheOtherDave comments on Ask and Guess - Less Wrong Discussion
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Guesser culture affords much more signaling of how well you understand people. People who correctly guess will come off as more intelligent, observant and understanding. It's like the difference between offering money and offering carefully chosen presents; money may be more efficient, but efficiency isn't the only factor coming into account.
Interestingly, Chinese culture seems much more guess-based than American culture, but in China gifts are usually in cash, not in presents. Maybe societies all need a way to signal understanding and social suaveness, but choose different mechanisms.
Yeah, I think that's true. Among communities that identify as smart, for example, I find it's common to obfuscate speech or explicitly set out puzzles for one another, and I think that serves a similar role... even though such communities (like most communities whose membership changes quickly) tend to be "Ask" subcultures.