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a question wearing a disguise, daring your brain to recognize the answer hiding in plain sight

means a puzzle phrased as a tricky question or statement, designed so the answer is concealed and must be cleverly worked out.

from From Old English 'rǣdan,' to interpret or counselthe same root that gives us 'read.' A riddle was literally a thing to be read, in the old sense of figured out. (The other 'riddle,' a coarse sieve, is a separate word from Old English 'hriddel'; the two only sound alike, though there's a tempting overlap in the idea of sifting for meaning.)

sphinx stakesOedipus solved one; losers got eaten alive
ancient sportBabylonians scratched riddles into clay 4,000 years ago
viking duelOdin won contests by asking unanswerable questions
legal weaponAnglo-Saxon riddles doubled as bawdy double-entendres
hobbit loreBilbo and Gollum gambled their lives on riddles
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