Rosalee Futch (KATE BOSWORTH) is a young woman who lives in a small West Virginia town with her dad Henry (GARY COLE) and works with her best friends, Pete (TOPHER GRACE) and Cathy (GINNIFER GOODWIN), in the local grocery store.
Oblivious to the fact that Pete is interested in being more than just friends with her, Rosalee dreams of what it would be like to meet movie star Tad Hamilton (JOSH DUHAMEL). She surprisingly gets the chance when she enters a "Win a Date with Tad Hamilton" contest concocted by his manager, Richard Levy (NATHAN LANE), and agent who's also named Richard Levy (SEAN HAYES).
With Tad being the poster boy for bad movie star behavior, his handlers hope that by pairing him up with some sweet young thing, his public image will change and enable him to land a big, lucrative acting role. Accordingly, they fly Rosalee to Los Angeles where the two have a pleasant date that ends when she doesn't fall prey to his Hollywood charm.
Her down to earth demeanor, however, impresses him enough that he follows her back to her small town where he hopes being with her will change him into a different sort of person. Not surprisingly, everyone there goes gaga over having a movie star in their presence. That is, except for Pete who finally decides he has to let Rosalee know how he really feels about her. From that point on, she must choose which of the two men she's going to date.