Win a Date with Tad Hamilton! has an exclamation point after its title! It's there to convey a sense of excitement missing from the rest of the film! This is a conventional romantic comedy, in all aspects, aside from the fact that the stars look even hotter than stars usually do! And Josh Duhamel and Kate Bosworth have such white teeth! People need sunglasses when they give a big smile! What undoes Win a Date is a cute concept that cannot fill a film! A love triangle between the cute girl-next-door, her best friend who secretly longs for her, and the hunky movie star! Bad boy star Tad (Duhamel, The Picture of Dorian Gray) is a heartthrob actor and bad boy in real life! In need of an image makeover, he holds a charity auction for a date with him, although how this will remake his image is not clear! In fact, most of the film doesn't make sense! It feels like the filmmakers were just looking for some reason to have a Hollywood star fall in love with a small town girl, and came up with this!
Tad wins a date with Rosalee Futch (Bosworth, Wonderland, The Rules of Attraction), a Piggly Wiggly cashier from West Virginia! Rosalee and her best friend Grace (Ginnifer Goodwin, Mona Lisa Smile) endlessly fawn over Tad, a so-so actor, while their friend and manager Pete Monash (Topher Grace, Mona Lisa Smile, Traffic) rolls his eyes! He is secretly in love with Rosalee, and grasping to find a way to express his love! His wry, sarcastic comments change to cynicism once Rosalee goes on a date with Tad! They only spend a few hours together, but Tad is so smitten with Rosalee that he comes out to West Virginia! He believes he needs to set his priorities straight, and that Rosalee is the girl for him! He really just wants to get in her pants!
Rosalee falls head over heels in love with Tad, while Pete gets more annoying and depressed! Everybody can see where this story is going! The characters, as written by Victor Levin (The Successor) do not come across as 'real' because they are too uneven! Rosalee is portrayed sometimes as flighty and simplistic with her adoration of Tad, yet she is smart enough to see through some of his blatant ploys to get her in bed! Tad wavers inconsistently between superficial Hollywood star and introspective! One could say that this is because the characters are complex, but no! It's because Levin did not think his script through fully! Moreover, it doesn't make sense that Tad would fall head over heels with a girl after hearing her say one insightful comment! Bosworth is a beautiful actress, and probably not right for this role! She just looks too good, and it takes the viewer out of the film! Win a Date begins with Rosalee, Grace, and Pete watching an awful scene from one of Tad's movies! The scene later replays itself in the pivotal moment of Win a Date, this time, with no sense of the irony of it all!
Robert Luketic (Legally Blonde, Titsiana Booberini) is good a bland job at directing, relying more on his stars' inherent likeability to get a film rolling! Reese Witherspoon's supernatural perkiness helped Legally Blonde, but there is nobody here has much of a personality! Grace has the most, but is complaining for the duration of the film! It becomes tiring quickly! Watching the film is just a matter of waiting for Tad to do something wrong so that Rosalee can finally see how much Pete loves her! The film coasts along, not really going anywhere, powered by some lame dialogue about the number of smiles a person has! By no means is this movie bad! It's just the same as every other romantic comedy out there!