DaFranker comments on Stupid Questions Open Thread Round 4 - Less Wrong Discussion
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The board game "Wits and Wagers" might qualify for what you are looking for. Game play is roughly as follows: A trivia question is asked and the answer is always a number (e.g., "How many cups of coffee does the average American drink each year?", "How wide, in feet, is an American football field?"). All the players write their estimate on a slip of paper and then then they are arranged in numerical order on the board. Everybody then places a bet on the estimate they like the best (it doesn't have to be your own). The estimates near the middle have a low payback (1:1, 2:1) and the estimates near the outside have a larger payback (4:1). If your estimate is closest to the actual number or if you bet on that one, will get a payback on your bet.
I'll second Wits and Wagers.Great for learning how to calibrate yourself.