With When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

The history of the modern-day romantic comedy goes something like this: Rom-coms were good, then they got really bad, then they went away for a while, and now they’re back with a vengeance. The exact details of that timeline, however, are a bit fuzzier. At the start of the 1990s, Hollywood was regularly producing rom-com classics like Sleepless In Seattle and Four Weddings And A Funeral. By the mid- to late-2000s, it was churning out shit like The Ugly Truth and What Happens In Vegas. So where did the rom-com genre go wrong? The 2008 film 27 Dresses is often cited as the ur-example of a bad aughts rom-com—unfairly, perhaps—but it’s possible the shift actually happened earlier than that. While no one can rightly claim that it caused the artistic downfall of the romantic comedy, in retrospect 2003’s How To Lose A Guy In 10 Days marks an unfortunate turning point for the rom-com genre.

In an oversaturated market, early ’00s romantic comedies relied on high-concept hooks to differentiate themselves. How To Lose A Guy In 10 Days has one of those, but what’s even more striking about the film is that its world has absolutely no texture. Whereas ’90s rom-com creative forces like Nora Ephron and Richard Curtis were great at creating eclectic, lived-in worlds, How To Lose A Guy In 10 Days is defined by its generic glossy sheen. Every outfit looks like it was hand-picked by a costume designer, every plot beat like it was written by committee. Director Donald Petrie had previously helmed the romantic comedy Mystic Pizza and the pseudo-rom-com Miss Congeniality, but failed to recapture the sparkle of those films in How To Lose A Guy In 10 Days. None of the film’s characters seem to have interior lives, and the supporting characters in particular feel like they freeze in place whenever the leads leave the room and only reanimate when it’s time to serve as their sounding boards. It’s a far cry from the delightful way When Harry Met Sally used Carrie Fisher and Bruno Kirby.

As with many cinematic trends, it’s hard to give full credit to, or place full blame on, just one film. Bryan Singer’s X-Men may have kicked off the modern era of superhero films, but Sam Raimi’s Spider-Man was already in development before X-Men was released. Similarly, How To Lose A Guy In 10 Days didn’t necessarily do anything that earlier rom-coms hadn’t already done, or that other contemporary rom-coms weren’t also starting to do. It just happened to coalesce a bunch of uninspired tropes in one place, and find a lot of success while doing so. The film made $105 million domestically, and had a big marketing push that made it especially ubiquitous. Images of Kate Hudson in the Dina Bar-El yellow dress from the film’s climax were everywhere, and the film felt even more pervasive once it became a mainstay on cable TV. (There’s even a How To Lose A Guy In 10 Days board game.) Unfortunately, Hollywood seemed to take the film’s success as proof that it didn’t actually need to put that much artistic effort into romantic comedies in order for them to find an audience.

The film is loosely inspired by Michele Alexander and Jeannie Long’s 1998 illustrated self-help book called How To Lose A Guy In 10 Days: The Universal Don’ts Of Dating. The movie keeps the book’s regressive “men are from Mars, women are from Venus” attitudes about dating, but adds a plot straight out of a Doris Day/Rock Hudson bedroom comedy from the early 1960s. Kate Hudson stars as Andie Anderson, an aspiring political journalist stuck writing shallow how-to columns for the Cosmo-esque magazine Composure. (The column she actually wants to write is called—no joke—“How To Bring Peace to Tajikistan.”) Mining content from the disastrous love life of her friend Michelle (Kathryn Hahn), Andie pitches a column called “How To Lose A Guy In 10 Days.” She’ll hook a potential love interest, and then drive him away by making all the “classic mistakes most women make” in a new relationship, which range from stocking his bathroom with tampons (the horror!) to buying a dog to co-raise with him after they’ve gone on four dates.

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It’s a goofy setup that’s at least somewhat justified by the goofy nature of Andie’s job (the movie inspired at least one real-life writer to try the same experiment), but the other half of the plot really strains credibility. Matthew McConaughey plays Benjamin Barry, a rakish advertising exec focused on the manly areas of alcohol and athletic equipment. He has his eyes set on a more lucrative diamond campaign, however, and comes up with an idea to market diamonds directly to women rather than the men in their lives. Ben’s boss is skeptical about the advertising sea change, so he decides to settle it with a bet: If Ben can prove he actually understands women by making one fall in love with him in 10 days (the date of the company’s big gala), he’ll land the diamond account that’s currently being managed by his more competent female coworkers. And since Ben’s workplace rivals already know about Andie’s column, they select her as Ben’s mark to ensure he doesn’t have a chance of winning the bet.

It’s such a bizarre, convoluted setup that it makes you wonder why screenwriters Brian Regan and Burr Steers didn’t just make Ben a rival journalist writing the opposite kind of article. This speaks to the overall laboriousness of the film. There’s humor to be found in watching Andie and Ben try to outmaneuver each other’s mind games while genuinely falling for each other in the process, but at some point it just becomes exhausting to watch Andie actively mistreat Ben in increasingly over-the-top ways. By the time she’s ruining his poker night with deranged baby talk and dragging him to fake couple’s therapy, the premise has been stretched far too thin.

It’s also a pretty cheap way for the film to have its cake and eat it too when it comes to gender politics. How To Lose A Guy takes great pains to establish that the real Andie is a “cool girl” who loves sports and chows down on burgers, so we’re free to laugh at her as she does the clingy, needy things “other girls” do to ruin their relationships. On paper, there’s something enjoyably subversive about a farcical rom-com where the woman is doing more of the manipulating than the man (it’s almost always the reverse). In practice, however, it just winds up being another comedy that treats women as punch lines. Like Hitch, How To Lose A Guy In 10 Days half-heartedly attempts some social commentary about dating in the 21st century, but the script is far too muddled to ever really land on an insightful thesis.

You could drive yourself crazy poking holes in the film’s premise (what if Andie had just immediately driven her beau away and had nothing to write about? Why didn’t Ben’s boss just do market research on Ben’s genuinely intriguing idea?), and the 10-day timeline feels far too short for either of the two scenarios in question. But, to be fair, How To Lose A Guy In 10 Days is mostly aware of how ridiculous it is. “Sounds needlessly vicious!” one woman laughs after hearing the premise for Andie’s column. What makes the film a watchable mess rather than an unwatchable one is the fact that its cast throws themselves into the material with real verve. In that way, How To Lose A Guy In 10 Days is a lot like Overboard, another hijinks-heavy rom-com in which the charm and chemistry of the two leads spice up a lackluster, frequently misogynistic script to the point where the film is far more fun than it has any right to be. Of course, that cinematic connection is also helped by the fact that Kate Hudson very much channels mom Goldie Hawn as the film’s screwball comedy star.

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Hudson was just 23 when she made How To Lose A Guy In 10 Days, still fresh off of her breakout debut in 2000’s Almost Famous. She starred in a couple other rom-coms around the same time, but How To Lose A Guy In 10 Days is the one that established her as a mainstay in the genre. And it’s not hard to see why. Even in the midst of the film’s most interminable cringe comedy scenes, Hudson usually earns at least one or two genuine laughs from her off-kilter delivery. And she’s great at silently conveying how ridiculous Andie finds the act she’s putting on. McConaughey—already a decade into his career at this point (he’s 10 years older than Hudson)—makes a great romantic straight man, and the laid-back way Ben handles Andie’s antics helps make the film far less exhausting than it otherwise could have been. McConaughey had previously starred opposite Jennifer Lopez in 2001’s The Wedding Planner, but How To Lose A Guy In 10 Days really kicked off his career as a major rom-com leading man of the aughts, laying the groundwork for his later McConaissance.

Most importantly, Hudson and McConaughey are really great together, especially in the scenes where Andie drops the clingy act and behaves like an actual human being. Andie and Ben have a particularly sexy meet-cute in which they exchange one-word phrases to quickly establish that they’re both single and interested in each other. Later, when Ben takes Andie home to Staten Island to meet his family, the film offers a glimpse of the much better rom-com that might have been made if Hudson and McConaughey were given more grounded material. (The duo did reunite for 2008’s Fool’s Gold, though that didn’t exactly deliver a low-key hangout, either.)

Like the earnest family subplot in Overboard, the Staten Island scenes attempt to inject some heart and humanity into an over-the-top comedy. It’s a lovely sequence in isolation, but it’s also a weird narrative and tonal swerve for the movie to make so late in the game. And it only brings the rest of the movie’s weaknesses into sharper relief. Even with barely any screen time, Ben’s Southern family members feel more like actual people than any of the other supporting characters. That immediately makes Ben appear more three-dimensional as well, while simultaneously driving home just how thinly Andie is written. Other than her vague desire to be a political writer—something that winds up playing in opposition to the film’s romantic ending—we know literally nothing about Andie’s life, or family, or the personal foibles that might define her character arc (if she had one). It’s as if the screenwriters completely forgot to write her half of the movie. In fact, it feels like the writers just gave up entirely after the Staten Island sequence. When their mutual manipulations are finally revealed, Ben and Andie duel it out in an anger-fueled karaoke performance the film barely invests in. And it invests even less in its perfunctory “race to stop your love from leaving town” ending.

How To Lose A Guy isn’t a complete failure, and it’s understandable why people have a lot of nostalgic affection for it. For the most part, it’s fun, watchable, and just knowing enough about its own ridiculousness. In fact, if the movie had cut back on the laborious comedy, upped the character exploration, and reworked its ending, it probably could’ve been a great rom-com. But as it stands, it’s just an okay one. Unfortunately, it’s also one that helped set the template for a whole decade of lackluster rom-com filmmaking. The movie’s big cultural impact isn’t really its fault, and the rom-com genre almost certainly would’ve gotten there without it. But it does make it harder to appreciate the film in its own right without seeing it as a cultural turning point. How To Lose A Guy In 10 Days almost gets away with its flaws, but later rom-coms wouldn’t be so lucky.

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Next time: Rom-coms (briefly) came out of the closet with In & Out.