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In the present, Chuck (Dane Cook) is a successful dentist in his thirties, and runs a dental practice in the same building as his best friend Stu's (Dan Fogler) plastic surgery business.
Chuck finds himself unable to tell his girlfriend, Carol (Chelan Simmons), that he loves her, and she breaks up with him while having sex on the beach.
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Following the break up, Stu and Chuck decide to attend the wedding of one of Chuck’s ex-girlfriends, Katie.