Win a Date With Tad Hamilton! (2004)

Review by All Movie Guide
For the first time in his film career, Topher Grace plays the kind of hands-in-pockets underdog hero that made him famous on the small screen, and it carries Win a Date With Tad Hamilton! pretty far. The other two-thirds of the love triangle -- Kate Bosworth as a perky convenience store clerk, Josh Duhamel as a studly movie star -- also work well, making the film a sweet little confection with a nostalgic 1950s ethos. The title itself hearkens back to a pre-ironic era when "dreamy" matinee idols made impressionable teens swoon, and the film is smart to keep that light sensibility, even set well within modern times. Events never careen toward the sensational, which means former TV scribe Victor Levin can give his characters the depth to exceed the one-dimensionality such a story might have engendered. In lesser hands, Duhamel's every move would have been laced with wrong intentions, while Grace would have been the "gracious" loser, as it were. Instead, Duhamel is fairly generous, and Grace fairly petty. It's amusing watching them jockey for position, trying to appeal to different aspects of Rosalee's persona, with Grace's Pete gradually losing any sway over her. Anyone in the audience who's lost a significant other to a flashier candidate will sympathize with the uphill task. The film has the pastel colorings and core sensibilities of director Robert Luketic's previous outing, Legally Blonde, without that film's oversimplifications and annoying caricatures. It's still essentially fluff, but it's slightly more substantial fluff. ~ Derek Armstrong, All Movie Guide