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Will's an aspiring chess master who's making all the wrong moves. He says that his troubled upbringing scares potential dates away, but his real problems seem to stem from a lack of confidence--he's out of shape, his apartment's a mess, and he can't cook anything fancier than a sandwich. If Will's ever going to find his mate, he'll have to learn the rules of the game.
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Can't Get a Date (2006) - 1x06 - Will