Written by: Victor Levin
Starring: Kate Bosworth, Topher Grace, Josh Duhamel, Sean Hayes, Nathan Lane
Rating: [2/5]
Stories centered on the revelation of long-held unrequited love have the task of not only convincing the audience why it will work out but also what took everything so long to happen. Something we see occur aplenty in romantic comedies with the best friend character as seen in Win a Date with Tad Hamilton! Nothing necessarily out of the ordinary except for the simple fact that nothing from the screenplay and character work succeeds in having us root for who they want to.
In a small town in West Virginia, Pete (Topher Grace) plans to go off to college in Richmond and wants to take his best friend whom he secretly loves Rosalee (Kate Bosworth) with him. However, Rosalee wins a contest where she can go on a date with Hollywood actor Tad Hamilton (Josh Duhamel). When she thought it would only be a one-time thing, Tad takes a real interest in her, much to the chagrin of Pete.
It’s almost impressive just how badly this film handles the central love story in a way that continually astounds. One confusing narrative decision after another where the story wants us to yearn and root for Rosalee to finally see the truth that she should end up with Pete where it left me wanting her to run away from him. Sure, that’s the way the story would always go but what we receive in Pete reaches a character type that has no business being near women, let alone trying to display him as someone anyone should aspire to act like. He exudes a type of loser energy where I simply refuse to believe anyone would find him attractive even if for just his personality.
This dreadful journey begins when Pete watches a film starring Tad with Rosalee where she speaks on the romanticism the actor exudes and we have cynical Pete just trying to ruin everything for her. This, at first, shows him as very annoying but things get much worse when Rosalee wins the date with Tad and Pete well and truly shows her true colors. In a sense, as a friend, you could see why he would feel protective of her spending time with a Hollywood actor known for using women for his pleasure. Putting him in the same space as a very doe-eyed and somewhat naive Rosalee could lead to some heartbreak but how he goes about this persuasion becomes quite strange. From describing her virginity as her “carnal treasure” she needs to protect to acting like a child for the majority of the film it begs the question of why we would root for Rosalee to see the light and fall in love with him.
It certainly also does not help when you have Tad Hamilton played amicably by Josh Duhamel to have quite the charm to him. Sure, in the beginning stages of the film, we see a guy who does not look forward to going on a date with some random girl from West Virginia but the man shifts in the way he views her upon meeting for their date. When he continues to pursue her by spending some time in West Virginia the difference between him and the always grumpy Pete continues to confuse me why we should not root for Tad and Rosalee to end up together. It makes no sense whatsoever. This film seeks to want us to care for the feelings of a particular guy who respects women until they do things he does not want them to do. A type of toxic friend who likes to act like a nice guy until he sees it will not get him what he wants and then lashes out against the people around him. Truly a childish motive and a terrible character that brings further rot to the center of this story.
Certainly not the best the romantic comedy genre has to offer, there remains not much to take away positively from Win a Date with Tad Hamilton! A film so confused about the morals of its characters and how it views Rosalee. Instead of a fully realized character played decently well by Kate Bosworth gets trapped with someone who feels like a delicate flower rather than an actual human being making this quite the unsettling film to watch. Pete stands out as one of the more embarrassing protagonists within this genre and fails to create not only a likable character but even one worth rooting for.
Films with Josh 
