Win a Date with Tad Hamilton! is sweet and cute and amusing, as well as derivative, unexceptional, and highly unlikely. Let's give it a draw and call it a mostly unoffensive diversion about the eternal starf***er phenomenon, a Notting Hill for the Teen Beat set. As scripted by Victor Levin (a dyed-in-the-wool TV-comedy scribe) and directed by Robert Luketic (Legally Blonde), Win a Date with Tad Hamilton! runs at a consistently droll and sprightly sitcom hum. If that sounds appealing, help yourself. If that sounds repellent, stay home.
Kate Bosworth puts on a shiny smile (retainer notwithstanding) as blonde girl-next-door Rosalee Futch. Along with her best friends Cathy (Ginnifer Goodwin) and Pete (Topher Grace), Rosie works at a Piggly Wiggly in her home state of West Virginia. I use the term "works" loosely as all three characters (including the inexplicably lackadaisical, distracted Employee of the Month Pete) have plenty of time to hang out together at work or take off whenever they please. They also don't read the checkout tabloids, or they'd know what trouble Hollywood ingenue Tad Hamilton (Josh Duhamel) has concocted for himself.
A paparazzo has sold a compromising shot of Tad to the Enquirer; as his agent Richard Levy (Nathan Lane) puts it, "Congratulations! You're actually drinking, driving, smoking, leering and groping at the same time." One also wonders if he's out on bail for the duration of the movie, but the real consequences of the DWI are never addressed. Sean Hayes plays Tad's blithe manager, also named Richard Levy. Oh, those Hollywood types are all the same.
So the Tinseltown trio agree on a scheme to promote Tad's goodness. He will go on a date/photo-op with a contest winner: Rosalee, it turns out. The hitch is that her harmless buddy Pete is in love with her, and about to pop a question (presumably, "will you go steady with me?"). Tad gracefully sweeps the seriously tongue-tied Rosalee off her feet (and tinkers with having a soul); the two teach each other lingo from their separate worlds, and opposites begin to attract. Meanwhile, Pete--who also has an unrequited lover--plots to win Rosie back.
Win a Date with Tad Hamilton! has enough going for it. It moves at a good clip. The cast is likeable, from the sunny Bosworth to the Michael J. Fox-y Grace, whose features seem to be in constant motion. Luketic stages an unbelievable but funny confrontation in a bar bathroom, and the gentle jabs at Rosalee's father (Gary Cole, wearing a Project Greenlight T-shirt and checking the Variety.com headlines) are good for some chuckles. In the end, goodness is sort of affirmed--though at least two lives are probably damned--and the romantic comedy dream-ending (following the tiresome guy-chases-girl-across-town climax) stamps "The End" on the silver screen.