First glimpsed giving an unbearably smarmy performance, Tad Hamilton (Josh Duhamel), it’s clear from the outset, might as well be called Cad Hamilton. That doesn’t prevent the even less probably named Rosalee Futch (Kate Bosworth) and Cathy Feely (Ginnifer Goodwin) from indulging in the kind of idol worship once reserved for Rudolph Valentino. Despite working in a supermarket, these fans have apparently never glanced at a tabloid. After a DWI scandal, Tad’s agent and manager (played by Nathan Lane and Sean Hayes and both named Richard Levy) order damage control. The solution: a “win a date with Tad Hamilton” contest to prove that T.H. is just like the boy next door. Rosalee is selected as the bait, much to the chagrin of boss/lifelong friend/secret admirer Pete (Topher Grace).
A less offensive concoction than Luketic’s Legally Blonde, Win a Date is nevertheless an oddity, unsure of its tone and even of what period it’s set in. Tad’s name and some of his roles (returning WWII vet, Old West lawman) suggest that he’s a holdover from the ’40s or ’50s. Rosalee’s West Virginia town—replete with vintage diner, lovers’ lane, and a movie theater with a neon marquee—also seems half-trapped in a time warp, her dad’s Project Greenlight T-shirt notwithstanding. Exuding naïveté, Bosworth is essentially playing an unironic version of Naomi Watts’s Mulholland Drive character, bewildered by airports and limos, saddled with gee-whiz mannerisms, and uncouth enough to place her retainer on the table at a fancy restaurant. All My Children player Duhamel’s lack of actual stardom (Ben Affleck and Hugh Grant were allegedly considered for the role) adds to the cognitive dissonance and precludes any Being John Malkovich-style (or even Notting Hill-worthy) self-reflexivity. The bizarre behavior on display would only be plausible if it were revealed to be part of a movie within a movie. Judging from the last shot, it just might be.