Win a Date With Tad Hamilton co-stars Kate Bosworth and Topher Grace once lived in the same small town. Playing small town residents in this new romantic comedy came naturally since neither friendly actor has really "gone Hollywood".

Hot actor Tad Hamilton (Josh Duhamel) has pulled one-too-many Colin Farrells. A tabloid picture has him drink, driving and womanzing..all at once. His agents (Nathan Lane and Sean Hayes), both named Richard Levy, want to repair his good guy image so they think up a contest. They'll appeal to the heartland with a Win a Date With Tad Hamilton contest! Tad will then show some lucky country bumpkin what a great guy he is and he'll be golden again.

In Fraziers Bottom, West Virginia at a Piggly Wiggly grocery store, two cashiers, Rosalee Futch (Kate Bosworth) and Cathy Feely (Ginnifer Goodwin), discover the contest on the internet and go ape! Tad is their absolute fave crush. The store manager Pete Monash (Topher Grace) has a huge lifelong crush on Rosalee but is afraid to ask her out.

Rosalee wins the contest and has a quick but impressive date with hottie Tad. She's freaked out by dogs in car seats and 9 dollar lemonade stands! He's smitten with this very "real" young woman. So much so that, when Rosalee returns home, Tad follows, determined to "find" himself and let some of Rosalee's goodness rub off on him. This launches the love triangle. Who will truly win Rosalee's heart?