‘Win A Date With Tad Hamilton!’ (2004) Review

Win A Date With Tad Hamilton! Synopsis: A small-town girl wins a date with a male celebrity through a contest. When the date goes better than expected, a love triangle forms between the girl, the male celebrity, and the girl’s best friend.

After a rowdy night ends up on the tabloids, famous actor Tad Hamilton (Josh Duhamel) finds out that the director of a movie he is desperate to be cast in is 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, so Win a Date With Tad Hamilton! is born.

In West Virginia, Tad’s 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 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 with Pete. Tad seemed to be searching for 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 much more on Rosalee and her blossoming romance with Tad than on 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?

Win A Date With Tad Hamilton‘s script is flimsy, without any originality. I 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 well. I don’t think Rosalee ended up with the right person, so the ending fell flat and seemed entirely 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.

I’ve been in a movie slump for a couple of months (thanks to COVID and all the other crappy things happening in the world), but I finally sat my butt down to watch a rom-com. Win A Date With Tad Hamilton was not the right choice to jump back into things, but I’m just happy my desire to watch movies again has returned. I hope you’re all healthy and staying safe!

Watched: 07/23/2020
Notable Song: Shining by Kristian Leontiou