"Win a Date with Tad Hamilton!" is very standard. It is neither rewarding nor disappointing. It's better than most romantic comedies in some ways, but worse in others, so it averages out. It is so average, in fact, that it's utterly forgettable.
The plot sticks pretty closely to a familiar formula: nice boy loves girl, girl loves more exciting man, girl eventually realizes that nice boy is her One True Love, girl ditches exciting man and lives happily ever after with nice boy. In this particular instance, the nice boy is Pete Monash (Topher Grace), a manager at a Piggly Wiggly in West Virginia. His lifelong best friend Rosalee Futch (Kate Bosworth) is the pretty girl at the center. And her celebrity crush, Tad Hamilton (Josh Duhamel), is the more exciting man who almost steals her away. Rosalee and Tad meet when she enters and wins the contest alluded to in the title. She is flown to Los Angeles for the magical date. Intrigued by her pleasant wholesomeness, he follows her back to West Virginia, and thus begins the love triangle.
"Tad Hamilton" isn't hilarious, but it has its moments. In a particularly amusing scene, the audience views Los Angeles through Rosalee's eyes. As she rides the limo from LAX to the hotel, she sees: a hitchhiker wearing nothing but a bikini (she holds a sign that reads "I left my clothes in San Francisco"), children selling lemonade at $9 a cup, a woman walking her kids as if they were dogs and a car with a dog strapped into the child seat as if it were a baby. More great humor comes from Nathan Lane and Sean Hayes as Tad's agent and manager, respectively, both named Richard Levy. Lane and Hayes play off of each other quite well and add some heartier laughs to the movie.
As a whole, the characters and cast are good, but not amazing. Romantic comedies tend to make the more exciting man a good-for-nothing cad and the nice boy a gentle romantic, but here Tad turns out to be a decent guy, even if he does party a lot. Pete, caring as he is, has a sarcastic streak-at one point, he threatens his rival with either physical violence or "vicious rhetoric." Duhamel avoids the temptation to go too over-the-top with Tad's more depraved antics, so we still think of him as a real, albeit somewhat clueless, person. Grace also has a knack for dead-pan sarcasm and self-deprecating charm. He and Bosworth have good chemistry and are fun to watch together. The most sincere moment in the film comes from Rosalee and Pete's shy, awkward first kiss.
Where "Tad Hamilton" falls apart, unfortunately, is in the romantic scenes. Deep speeches about how "great love" lasts a lifetime and can never be replaced have no place in a movie this light, and only weigh it down unnecessarily. Shorter, less serious monologues, with a better sense of humor, would have moved the film along better. The sentimental and supposedly moving dramatic scenes undermine the occasionally intelligent humour (usually produced by Grace), which is one of the movie's few strong points.
What makes this film so forgettable is the fact that it offers absolutely nothing that we haven't seen before. The jokes about Los Angeles are cute but unoriginal; the declarations of love are heartfelt but generic. "Tad Hamilton" pokes fun at conventions of the genre, but isn't really cheeky enough about it, and just ends up following those conventions all too well.
Ultimately, "Tad Hamilton" is likeable but not loveable. It is neither bad nor good, and I would neither encourage nor discourage you to watch it. If you like this kind of film, you won't be disappointed. If you don't watch it, though, you won't have missed much. It looks just like your average romantic comedy and it is. Very, very much so.