I’m going to get straight to the point: 2003’s How to Lose A Guy in 10 Days was the last of the great rom-coms. It has everything. A plucky 23-year-old Kate Hudson is coming off Almost Famous‘ huge success and delivers an incredible comedic performance, maybe the best of her career. What about the divine alliteration of its main characters Andie Anderson and Benjamin Barry? And who could forget that showstopping fashion moment in that floor-length yellow gown? It’s perfection.
The premise, in case you’re unaware, for How to Lose a Guy in 10 Days is this: Andie works in magazines; she’s Composure’s “How To” girl. Ben (Matthew McConaughey) is an advertising executive; he specializes in alcoholic beverages and athletic equipment.
In the opening scenes of the film, we learn that Andie’s colleague Michelle (Kathryn Hahn) gets dumped after exhibiting classic dump-able behavior. In the magazine’s pitch meeting, Andie gets an idea. She’ll use Michelle’s experience to write a “how-to in reverse”; date a guy for 10 days and do all the classic things women are told not to do in a relationship to drive him away.
Simultaneously, Ben is “trying to break into the jewelry market” by vying for the opportunity to pitch a potential client, DeLauer Diamonds over his professional rivals, the Judys. Over an after-hours work meeting he wasn’t invited to but insists he should have been, Ben makes his case for why he, a sports bro, should handle the pitch over two experienced women (who are obviously very good at their jobs). “The skills to market diamonds are the same as those needed to make a woman fall in love,” Ben says. “I love women, I respect women, that’s why I can sell myself to any woman.”
With prior knowledge of Andie’s assignment, Judy 1 gets an idea of her own. If Ben can get a woman to fall in love with him in 10 days, he wins the pitch. The catch is that the Judys get to choose the lucky lady and, as fate would have it, Andie is at the same, painfully over-lit Manhattan bar. Bring on neediness, baby talk, and matching Burberry outfits.
She starts as Cool Andie by taking Ben to a Knicks game. With about 5 minutes left on the clock, Crazy Andie takes over. She asks “Benny” to get her a drink, but he misses the end of the game because he didn’t get her a diet soda and must go back. The craziness intensifies when Jealous Andie berates him for a Valentine’s Day screening of Sleepless in Seattle because “you can’t spend two hours with Meg Ryan and not be thinking about another girl.” What a line.
Girly Girl Andie gussies up Ben’s apartment with women’s things: stuffed toys, Shania Twain, and Sheryl Crowe CDs (“the gang’s all here!”), and fills his bathroom with lacy pink hand towels and tampons, oh the horror! And how could we forget the love fern? But it’s not enough. She’s “clingy, needy, whiney,” but concedes she could kick “the babytalk” up a notch. It’s DEFCON5. Time to infiltrate boys’ poker night.
She might be the epitome of unlikeable and shrill, but Hudson’s performance is so far from annoying, here. She’s impossible to not like, even when she makes the boys swap pizza for cucumber sandwiches, put out their cigars, and yells at Ben about letting their love fern die. Therein lies her genius.
They nearly break up there and then, but Ben’s colleagues refuse to let him give up. The solution? Couple’s therapy with Michelle posing as a therapist and a trip to Staten Island to visit Ben’s family. For inexplicable reasons we’re totally fine with, Andie goes back to her regular cool-girl programming. It’s clear they’re genuinely starting to fall for each other after they play Bullshit with his family, take motorcycle lesson on the boardwalk, and… have sex in his parent’s bathroom? Why not.
At the black-tie gala for DeLauer diamonds; we get that yellow dress moment which was created by Carolina Herrera’s team in collaboration with the film’s costume designer. More than 20 years later, there are still articles on where to buy the dupes, such is a sign of its immediate and long-lasting impact.
Both Ben and Andie’s deadline for their faux relationship is up and their deceptions are finally laid bare. “You wanted to lose a guy in 10 days, congratulations, you did it. You just lost him,” he says. “No, I didn’t Ben, ‘cause you can’t lose something you never had!” Queue the reflective article where Andie spills her soul about losing “the only guy I’ve ever fallen for.” She leaves New York, and Ben chases after her on the way to the airport.
The film was made for $50 million back when actors had the time and money to prepare for a rom-com. Matthew McConaughey bought a motorcycle “because I’ve seen too many people ride motorcycles or someone ride a horse in films where I’m like, ‘You don’t really ride a horse. You don’t really ride a motorcycle.” Ok, Matt. Kate Hudson, meanwhile, actually shadowed Vogue’s Anna Wintour for a day. It inspired a generation of female journalists in the process and made $177 million worldwide at the box office.
“It’s actually quite [a] feminist movie, and I think that really resonates with young girls: The concept that women are in control of their own destiny, their own life, and their own purpose, and the fact that Andie is a journalist [who’s] working a job that isn’t really what she wants to be doing, and she chooses to pursue her dream,” Hudson told Vanity Fair in honor of the film’s 20th anniversary. “It’s a very strong female character that a lot of women connect to.”
Hudson and McConaughey would reunite for Fool’s Gold in 2008 and while they undeniably have chemistry, the magic of Andie Anderson and Benjamin Barry is just not there in the same way. While Hudson would evolve into the self-important, vindictive best friend in films like Bride Wars and Something Borrowed, McConaughey would leave rom-coms in the dust, winning an Oscar for Dallas Buyers Club in 2014.
How to Lose a Guy in 10 Days marks, in my mind, the end of the rom-com era. It plays with all the classic tropes of the genre but does so with a level of self-awareness rarely seen in anything other than parody films. Even then, they’re not so delicately balanced. It’s about how men expect women to behave and “what women do” that drive men insane, but unlike other films that had come before it, Andie isn’t the butt of the joke, she’s in on it.
