Kate Bosworth plays Rosalee Futch, a grocery store checkout girl from a small town in West Virginia who wins a date with Tad Hamilton (Josh Duhamel), a famous Hollywood actor, in a contest. Rosalee is excited to meet Tad, but her best friend and co-worker, Pete (Topher Grace), is skeptical of Tad's intentions.
When Tad arrives in town and meets Rosalee, he is smitten and decides to stay in town for a while. As Tad spends more time with Rosalee, they begin to develop feelings for each other, much to the dismay of Pete, who has secretly been in love with Rosalee for years.
As Rosalee navigates her feelings for Tad and Pete, Tad's manager, Richard Levy (Sean Hayes), sees an opportunity to capitalize on Tad's image as a wholesome, down-to-earth Hollywood heartthrob. Richard encourages Tad to pursue a relationship with Rosalee and even arranges a publicity stunt to make it seem like Tad is proposing to her.
In the end, Rosalee must choose between Tad, who represents the glamorous, exciting life of Hollywood, and Pete, her loyal and supportive best friend who has been by her side for years. The movie ends with a twist that surprises everyone, including Rosalee.