To Hollywood types, small-town America exists more as a concept than an actual locale; it's so alien to their own experiences that flyover country might as well be Belize. Judging by recent films such as Sweet Home Alabama, Mr. Deeds, and the tepid new romantic comedy Win A Date With Tad Hamilton!, screenwriters take it on faith that things haven't changed much since the '50s: A typical date night includes a trip to the single-screen movie palace, a bite at the greasy-spoon diner, and perhaps a brief make-out session at the ridge. (Don't get too fresh, boy. She's not that kind of girl.) Tagging small towns as wholesome and substantial and big cities as shallow and corrupt is a convenient shorthand, but it doesn't go far in distinguishing one fish-out-of-water scenario from another, no matter how appealing the stars are. With his canny mix of arrogance, charm, cynicism, and soul, Topher Grace isn't the most obvious choice for a go-getting young Piggly Wiggly manager in industrial West Virginia, but his quirky line-readings and gestures knock Win A Date pleasantly off-balance. Based on his few appearances outside TV's That '70s Show–most notably a scene-stealing turn as a righteous prep-school druggie in Traffic–Grace deserves a smarter introduction as a leading man, instead of roles that make him gag through windy speeches about his crush's "six different kinds of smiles." As it is, Grace and the appealing Kate Bosworth (Blue Crush) squeeze an old fairytale formula for all it's worth, just as Reese Witherspoon did with director Richard Luketic's last high-concept comedy, Legally Blonde. After tabloid dirt threatens to soil hunky marquee idol Josh Duhamel's squeaky-clean image, his handlers go on damage control, announcing a "Win A Date" promotion to restore his reputation. The stunt backfires when Bosworth wins the contest, flies out to Los Angeles, and charms Duhamel so much with her sparkly goodness that he follows her back to West Virginia. Sensing that Bosworth will favor the ripped Hollywood charmer over a guy who thumbs through Modern Grocer magazine, Grace fights hard to win her over, but his near-pathological jealousy seems like the wrong tack. Win A Date sputters through weak gags contrasting Duhamel's world (Segways, kids on leashes, $9 lemonade stands) with a rustic backwater where the local motel doesn't even have a masseuse on staff. Add to that the buy-this-soundtrack segues and soppy romantic monologues (the script gets a Geo's mileage out of the "six different smiles" thing), and the film only surprises on the margins. The great character actor Gary Cole, in particular, stands out as Bosworth's father, who tries to impress Duhamel by reading the trades, thumbing through Julia Phillips' autobiography, and donning a Project Greenlight T-shirt. He and Grace seem incapable of giving uninteresting performances, but they shouldn't be resigned to transcending the generic.