Win A Date With Tad Hamilton! opens with a movie within a movie: a cheesy 1940s-set romantic melodrama where everything is resolved with a single gesture. “I wonder if these two get together,” one guy in the audience snarks while his two young female friends melt into puddles of happy tears. It’s a silly, self-aware opening that’s a touch reductive but not entirely unfair. I should know, I was once a young teenager who excitedly ventured out to see Win A Date With Tad Hamilton! with a fellow rom-com loving friend during our freshman year of high school. If we didn’t exactly melt into puddles of tears by the end, we certainly felt like we got our funny, swoony money’s worth.
Though I pride myself on having had fairly good rom-com taste as a teen, I had no idea how I’d feel revisiting Win A Date With Tad Hamilton! a decade and a half after it was in regular rotation as one of my favorites. While Josh Duhamel will always be Tad Hamilton to me, the movie landed with a thud at the box office and hasn’t had any real cultural staying power since. How would its 2004-era Hollywood fairy tale play now that Duhamel has moved on to playing rom-com dads and star Kate Bosworth (and to a lesser degree Topher Grace) have long since faded from the zeitgeist?
Well, I’m pleased to report that while Win A Date With Tad Hamilton! isn’t quite as good as I remembered, it’s also far better than I feared it would be. What She’s All That is to the late 1990s, Win A Date With Tad Hamilton! is to the mid-2000s: a teen movie that exaggerates the excesses of its an era in a way that toes the line between satire and celebration. Though several Paris Hilton cameos wound up on the cutting room floor, Win A Date With Tad Hamilton! has a half-mocking, half-enthralled take on the excesses of celebrity culture that feels distinctly 2004. As do the low-rise jeans, stick straight hair, non-stop pop songs, glossy cinematography, and garishly vibrant costuming.
Yet for all its period-specific details, Win A Date With Tad Hamilton! also has a certain wholesome innocence that makes it unexpectedly timeless too. Though it was directed by Legally Blonde’s Robert Luketic, it really reminds me of the Doris Day-Rock Hudson bedroom comedies of the late 1950s and early 1960s. Like those colorful baubles, Tad Hamilton has a winking, playful sense of self-awareness that lets you know the filmmakers are in on the joke, even if the story can’t entirely overcome the limitations of its era. It’s a movie aimed squarely at teen girls that (mostly) respects its intended audience. And that makes it exactly the sort of bright, romantic trinket that tended to earn a disproportionately harsh critique, especially in the 2000s.
The plot centers on Duhamel’s Tad Hamilton, a bad boy movie star desperately in need of an image rehab. (“I’m the boy next door, if you happen to live in a very dysfunctional neighborhood,” he explains.) Hoping for a rebrand, his agents (Nathan Lane and Sean Hayes) concoct a “win a date” PR stunt that pairs him with superfan Rosalee “Rosie” Futch (Bosworth), a Piggly Wiggly employee from Fraziers Bottom, West Virginia. After her sincerity wins him over during their date night, however, Tad decides that being around Rosalee’s wholesome small-town goodness is exactly what he needs to finally give meaning to his vapid movie star life—much to the chagrin of Rosalee’s lovesick lifelong friend, Pete Monash (Grace).
One of the best things about Win A Date With Tad Hamilton! is that it doesn’t present either corner of its love triangle as a villain. The stakes come from Rosalee figuring out what she wants her future to look like, not sussing out a rat. And Duhamel’s pitch-perfect performance offers just the right blend of earnestness and vanity that characterizes so many real-life movie stars. (Tad is exactly the sort of hot, dopey celebrity who would absolutely get sucked into some kind of New Age cult.) Duhamel won the title role by sending in footage from a soap opera convention, where he was mobbed by fans of his work on All My Children. And the movie mines both comedy and empathy from how strange it is for Tad to live inside the surreal bubble of fame. There’s a funny running gag where Rosalee’s dad (Gary Cole) scans Variety box office reports to try to make casual industry small talk.
Rewatching the film with adult eyes, however, the performer who impressed me most is actually Bosworth. She’s got a tricky role to play, as she has to make Rosalee feel like both an empowered modern woman and a retro throwback to toothy 1950s innocence. It’s remarkable how well she pulls it off, especially on the heels of her pricklier breakout performance in 2002’s Blue Crush. In Bosworth’s hands, Rosalee is earnest, optimistic, and a tad ditzy but never entirely naïve either. Beneath her bubbly exterior is some welcome self-possessed integrity. It’s a sort of Drew Barrymore grounded sweetness mixed with Sandra Dee lightness that holds the entire film together.
Where the movie stumbles, however, is with Topher Grace’s Pete, patron saint of “nice guys” everywhere. Even as a fan of the “friends to lovers” trope and even as someone who watched enough That ’70s Show reruns to imprint on Grace in some fundamental way, Pete is a lot to take. He’s the sort of snarky, insecure nerd archetype that wasn’t great in the 2000s but has aged really poorly today. (See also: Seth Cohen on The O.C.) And while you can sort of see what the movie is going for in contrasting Tad’s outward charms with Pete’s hidden inner depth, the whole things is tied up in the messiest aspects of the nerd reclamation movement that kicked off at the start of the 21st century.
Indeed, though Win A Date With Tad Hamilton! is ostensibly a female-wish-fulfillment narrative, it can’t quite stop itself from shifting into a male-wish-fulfillment fantasy at times too. It’s far easier to understand why Pete would want to date Rosalee than why Rosalee would want to date Pete, who’s never really anything but sarcastically condescending to her. You could improve this movie immensely by making Pete a kinder, more supportive character from the start, but that wasn’t the sort of thing that was in vogue in 2004. Which is too bad because Grace is better in the sweet moments than the snarky ones anyway.
Still, if the screenplay by sitcom writer Victor Levin has some flaws on a character and plot level, it’s elevated by dialogue filled with lovely, unusual turns of phrase. When Rosalee’s best friend Cathy (Ginnifer Goodwin) makes her promise to give detailed descriptions of what exactly Tad smells like, Rosalee responds, warmly, “I will bring you similes.” And when a despondent Pete seeks out wisdom from the tough-talking bartender (Kathryn Hahn) who’s long had a crush on him, she neatly sums up the power of infatuation: “Everybody is Tad Hamilton to somebody, Pete. Rosalee is Tad Hamilton to you. And you’re Tad Hamilton to me.”
The characters in Win A Date With Tad Hamilton! almost seem to speak their own language at times, which helps give the film its heightened, timeless quality. “You can’t love someone for what they stand for or what they seem to be. You have to love them for their details,” Rosalee tells Tad.” And that’s why Win A Date With Tad Hamilton! still works despite its Pete-sized flaws. This is a rom-com that’s both cozily familiar and quirkily specific. And while Win A Date With Tad Hamilton! doesn’t offer a particularly believable depiction of the sex and dating lives of 22-year-olds, that’s part of what makes its dreamily nonthreatening romance feel tailor-made for teen audiences.
Indeed, the movie ends with a sweet full circle moment, where Pete comes to see the value of the rom-com romanticism he initially mocked in Tad’s movies. Win A Date With Tad Hamilton! is well-crafted in the way it can lovingly laugh at rom-com tropes without belittling the genre as a whole in the process. It celebrates how rom-coms bring us joy, without suggesting that those who like them therefore lose sight of the line between fiction and reality in their own lives. That makes Win A Date With Tad Hamilton! a sort of love letter to young rom-com fans, one that arrived just when I needed it.
Next time: The gorgeous perfection of Joe Wright’s Pride & Prejudice.