A magazine columnist and advertising executive have competing agendas in the New York-set romantic comedy How to Lose a Guy in 10 Days.

Andie Anderson (Kate Hudson) is a New York magazine columnist at Composure, frustrated by writing fluffy “How to” articles and wanting to write more serious fare. When her friend Michelle (Kathryn Hahn) suffers another breakup, Andie decides to pen a daring piece: “How to Lose a Guy in 10 Days.” She plans to date a man and deliberately drive him away using classic mistakes women make, all while keeping her true motive secret.

Advertising executive Benjamin Barry (Matthew McConaughey) wants to move beyond sports and beer and hopes to prove he can pitch to women for a major diamond campaign. At a bar with his boss Phillip Warren (Robert Klein) and coworkers Judy Spears (Michaela Michele) and Judy Green (Shalom Harlow), he wagers he can make any woman fall in love with him. Spears and Green select Andie, knowing that she has her own agenda.

As their relationship begins, Andie sets out outrageous schemes to repel Ben, including sabotaging a New York Knicks game, crafting a scrapbook of future children, and overstocking his apartment with feminine hygiene products. Ben’s patience is tested, especially during a poker night, but with encouragement from friends Tony (Adam Goldberg) and Thayer (Thomas Lennon), he continues pursuing her. A trip to Staten Island introduces Andie to Ben’s warm, welcoming family, and she starts to genuinely care for him.

At the company ball, secrets and misunderstandings erupt. Andie learns of Ben’s bet and tries to humiliate him, prompting a public argument and breakup while Marvin Hamlisch plays piano. Later, Ben reads Andie’s heartfelt article expressing love for him. Racing after her taxi, he confronts her in Washington, D.C., and they finally confess their true feelings, reconciling with a kiss.

If you had told me that How to Lose a Guy in 10 Days was based on a picture book, you would have fooled me. In many ways, it started as a humorous response to The Rules, a dating guide of dos and don’ts for women. As a film, the premise is entirely predictable but at the same time, one cannot deny just how charming it is. Both Kate Hudson and Matthew McConaughey have great chemistry together on screen, so it comes as no surprise that they would later reunite in Fool’s Gold.

Romantic comedies live and die by their screenplay. How to Lose a Guy in 10 Days eventually came together with a focus on a female journalist working for an Anna Wintour-esque editor two years before The Devil Wears Prada was released in theaters. Thankfully, they brought on a guy to write for Benjamin Barry, and it worked to make the film even stronger. Ultimately, they’ve crafted a story in which the audience is actively rooting for them to end up together. That being said, they could have made more effort in some of the hijinks, but I’ll get to that momentarily.

In How to Lose a Guy in 10 Days, Karen Patch puts in spectacular work in her costume design. It’s not just matching Kate, Matthew, and the dog. Working with Carolina Herrera, they deliver one of the film’s crowning achievements in Kate Hudson’s yellow dress for the company gala. The dress ended up getting knocked off in stores for the next two years. Who wouldn’t want to wear that dress?!?

As for the production itself, the film is wholly based in New York. It’s a city that’s been overused in romantic comedies, but there’s so much about New York that is photographed beautifully on screen, not to mention the wealth of locations the city offers. How to Lose a Guy in 10 Days uses the city in a way that works to its advantage. The core characters are located in Manhattan and are fully aware of how they’re seen when they walk around, while Benjamin’s family lives in Staten Island.

How to Lose a Guy in 10 Days is a comedic battle of the sexes. All the bets going on just add to the humor. In any other film, Andie and Benjamin might end up together, but without the bets, maybe it would be without all the hijinks. There’s sexual tension between them, but there’s also this sense of authenticity. We see it in their relationship at the beginning, but because of the column, she’s doing everything to drive him away. Only when we get to meet his family in Staten Island do we really begin to see the difference in their relationship.

Of all the hijinks in How to Lose a Guy in 10 Days, the cruelest—next to making Benjamin miss the final minute of the New York Knicks-Sacramento Kings game—is when Andie mentions having “front row seats, right in the action” and further describes the seats as ones where “you can smell the sweat.” Benjamin is a sports guy, so he should know how the NBA Finals work. Instead, the film soon defies the space-time continuum. If you can live with this, fine, but for those of us who are into both rom-coms and sports, you have to suspend a lot of disbelief for the joke to work.

In how it is worded, we’re made to think it’s NBA Finals Game 3 between the Knicks and the Kings, only to cut to them leaving the Celine Dion concert at Madison Square Garden of all places. But here’s the thing: Celine Dion was drawing large concert arena crowds while riding the post-Titanic wave and would definitely not perform in a smaller theater while the Knicks are playing a home game during the Finals! The other thing is that if the Knicks hosted Games 1–2, they would be on the road for Game 3. Romantic comedies like How to Lose a Guy in 10 Days can play with reality, but only for so long.

And then there’s watching Sleepless in Seattle during the Chick Flick marathon at the movies. Going to the movies isn’t the problem—it’s the constant talking to each other to the annoyance of everyone else in the theater. I can’t blame the sensitive moviegoer (Tony Longo) for punching Benjamin in How to Lose a Guy in 10 Days. Believe me, many of us would have done the same. I don’t care who you are and what you’re trying to do to drive someone away—a movie theater is just not the place for conversation, not while the film is playing.

At the end of the day, How to Lose a Guy in 10 Days is exactly what it promises: a playful, predictable rom-com with enough charm, chemistry, and ridiculous hijinks to keep you entertained. It’s not perfect, and some jokes require a suspension of disbelief, but the heart of the story—watching Andie and Benjamin navigate their messy, hilarious, and surprisingly authentic relationship—makes it hard not to root for them all the way through. Whether you’re in it for the laughs, the wardrobe, or the sweet romantic payoff, the film delivers on nearly every front.

DIRECTOR: Donald Petrie
SCREENWRITERS: Kristen Buckley & Brian Regan and Burr Steers
CAST: Kate Hudson, Matthew McConaughey, Adam Goldberg, Bebe Neuwirth, Michael Michele, Shalom Harlow, Robert Klein, Kathryn Hahn, Thomas Lennon, Celia Weston, Annie Parisse

Paramount Pictures released How to Lose a Guy in 10 Days in theaters on February 7, 2003. Grade: 4/5

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