The cleverest thing about Win a Date With Tad Hamilton! is its title, which makes the film sound like a reality contest posing as a teen romance. Tad Hamilton (Josh Duhamel) is a bad-boy movie star in dire need of an image makeover. Hence the prefab date sweepstakes, which is won by Rosalee, a small-town West Virginia grocery clerk who, as played by Kate Bosworth, looks and acts like the most virginal, gleaming-white-toothed Miss America contestant from 1965. Her naïveté is meant to be so charming that after a single chaste evening, Tad follows her back home, wooing her to the thrill of everyone in town except Pete (Topher Grace), her coworker, who’s secretly in love with her.
”Win a Date With Tad Hamilton!” may find an audience, but I found it to be a leftover John Hughes triangle, with the acid-tongued motormouth Topher Grace, his hair unaccountably spiky-moussed so that it looks like he’s wearing a mud pack on his head, squirming his way through the Jon Cryer role. He and Bosworth are supposed to be made for each other, but they act as if they were barely meant to be friends. When she asks, ”Do you feel like it’s possible to love somebody your whole life and never really realize it?” I had an answer in mind, but it wasn’t the one the movie wanted.