Rosie (Kate Bosworth) is a West Virginia grocery store clerk who heads to Hollywood when she wins a dream date with Tinseltown's hottest eligible bachelor, Tad Hamilton (Josh Duhamel). But instead of the obligatory date-and-dash she expects, a bizarre love triangle forms between Tad, Rosie, and her best friend (Topher Grace), a fellow clerk who has had a crush on Rosie since grade school.