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Robert Luketic (Legally Blonde) directs the romantic comedy Win a Date With Tad Hamilton! from a screenplay by TV scriptwriter Victor Levin. Famous Hollywood actor Tad Hamilton (soap opera star Josh Duhamel making his film debut) is trying to promote his new movie. His manager (Sean Hayes) and his agent (Nathan Lane) both convince him to participate in a dating contest in order to improve his bad-boy image. The contest is won by Rosalee Futch (Kate Bosworth), an attractive young checkout girl who works at a Piggly Wiggly in West Virginia. When Tad ends up falling in love with her, he's willing to give up big-city life and move to small-town America. Meanwhile, her best friend and co-worker Pete (Topher Grace) is finally motivated to reveal his secret crush on her. Rosalee finds herself in the middle of a love triangle between her closest friend and a dream date.