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The story begins with a reverse chronological narrative that recounts the entire process of how Tank (played by Dane Cook) messes up a date. His job is to help men who have been dumped by their girlfriends by dating their ex-girlfriends and making them disgusted with each other. This way, the girlfriend feels nostalgic about her ex and is more likely to reconcile. However, Tank's latest task comes from his friend Dustin (played by Jason Biggs). The latter is struggling to win back his girlfriend Alexis (played by Kate Hudson) while watching a suave guy get close to her at work, feeling utterly helpless. Thus, he turns to Tank for help. They set some rules, and then Tank gets to work. Starting with a jogging session, he becomes Alexis's constant companion, and their relationship quickly intensifies to the point where Tank can't believe how much he has come to rely on this girlfriend. Feeling troubled, he turns to his experienced father (played by Alec Baldwin) for advice, but the latter encourages him to take the opportunity at his friend's expense, leaving Tank feeling torn...
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