"Win a Date With Tad Hamilton" begins with the contest it's named after. Promos for the event start flying along with the opening credits, and naturally they reach Rosalee Futch, a West Virginia grocery clerk who dreams her most romantic dreams at the movies.
Tad's her favorite star, so she jumps at the chance of winning a glamorous Hollywood evening with him. And win she does - little realizing Tad is a fast-living hedonist whose agent cooked up the contest because going out with a good girl from the heartland would clean up his image a little.
Then we discover Tad has a serious side, reading Flannery O'Connor when he isn't busy nightclubbing. A few hours with Rosalee's sweet country ways are enough to make him reshape his priorities from the bottom up. Quicker than you can say "cookie-cutter plot," he's followed her to her hometown, explained that he wants to be "just friends" so her "goodness" will rub off on him.
While this is nice for Rosalee, it's the opposite for Tad's greedy agent.
And it's disastrous for the insecure supermarket manager who was about to declare his own love for Rosalee when Tad barged into the picture. Things get worse when Tad decides he truly loves Rosalee and wants to be more than just friends.
What's best about "Win a Date" isn't what happens in the story but the way it's acted by a cannily chosen cast. Kate Bosworth and Josh Duhamel are exactly right as Rosalee and Tad, and the same goes for Nathan Lane and Sean Hayes as Tad's agent and manager - both named Richard Levy, and both utterly unsurprised at this coincidence, in one of the comedy's many offbeat jokes.
Even better is Topher Grace as the shy guy who's loved Rosalee all along; he's subtle and surprising in a part that could have been trite. Kudos also go to Victor Levin's screenplay, far more literate than you'd expect from a January teenpic, and Robert Luketic's low-key directing.
"Win a Date" isn't as funny as it wants to be, but it has a sheer pleasantness that stands out in this season of heavy-handed entertainments. Keep your expectations modest and you'll win a fair return for your box-office money.
• Rated PG-13; contains sexual content.