After a rowdy night ends up on the tabloids, popular actor Tad Hamilton (Josh Duhamel) finds out that the director of a movie he is desperate to be cast in is “taking a breath”, not entirely sure Tad is the right kind of actor for the part. In a desperate move to clean up his image, his agent suggests holding a contest to benefit charity, and so Win a Date With Tad Hamilton! is born. In West Virginia, Tad fangirl Rosalee (Kate Bosworth) and her friend Cathy (Ginnifer Goodwin) raise the $100 charity donation required to enter the contest. While Rosalee is busy daydreaming about Tad Hamilton, her best friend Pete (Topher Grace) is getting ready to move to Richmond for school, and preparing to finally reveal to Rosalee that he’s in love with her.
But of course, things go astray when Rosalee wins the contest and is swept away to Los Angeles for her date with Tad. Expecting a bumpkin, Tad is a bit resistant to the date until he actually meets Rosalee. Despite a shaky start, Rosalee and Tad hit it off and Tad is so charmed by the down to earth Rosalee that he follows her back to West Virginia to spend more time with her and try to find more simplicity in his own life, thus derailing Pete’s confession of love all over again.
The issue with Win A Date With Tad Hamilton is that Rosalee had much more chemistry with Tad than she did with Pete. It seems like Tad was searching for something more than an endless parade of beautiful women and a good time. He had flaws, sure, but he wasn’t an entitled douche. The movie focused a lot more on Rosalee and her blossoming romance with Tad than it did with her relationship with Pete. Not to mention Pete’s behavior towards Tad and Rosalee was borderline creepy and stalkerish. Instead of trying to sabotage their dates, he could have just been honest with Rosalee from the get go, yes?
The script itself is pretty flimsy without any real originality. I do adore the best friends to lover trope and I love the rich and famous falls for the small town girl/guy… this movie has both, but fails to execute either of them terribly well. I don’t think Rosalee ended up with the right person, so the ending fell flat and seemed completely out of place compared to the rest of the movie. Honestly? Pete should have realized what a gem he had in Angelica, the “wise” bartender in love with him (played by the always reliable Kathryn Hahn). This is just another cookie-cutter rom-com. It has a fun premise but is sadly a huge disappointment.