HOW TO LOSE A GUY IN 10 DAYS, Annie Parisse, Kathryn Hahn, Kate Hudson, 2003, (c) Paramount/courtesy
Credit: Everett Collection

Kathryn Hahn is still recovering from her best friend phase.

She got her start in Hollywood as the sidekick to many an A-list actress — she played Cameron Diaz’s assistant in The Holiday, Christina Applegate’s confidante in Anchorman, Amanda Peet’s partner-in-crime in A Lot Like Love — in roles that were meant to be supporting but that often, perhaps unbeknownst to whoever cast the movie, ended up stealing the show outright. Her best friends were often the clear favorite, a trend that started with How to Lose a Guy in 10 Days.

The romantic comedy debuted 15 years ago today and quickly became the stuff of legends: A barometer in which to measure all others in the genre, an endlessly quotable meme-fest before memes were even a thing. And in a story line culled straight from a rom-com itself, it was Hahn’s very first movie.

She was, as she can recall, barely a year out of graduate school and working on NBC’s Crossing Jordan, with a storage unit in Brooklyn that she hesitated to give up in case things didn’t work out. She made it through several rounds of auditions and was invited to the Paramount studios to read for the director alongside Kate Hudson, who had already been cast in the lead.

“I was so nervous, I remember I broke the ice by joking about the horny summers at this theater camp we had both been to when we were kids,” she told EW of her first meeting with Hudson. “Even though I had a boyfriend at the time, so it wasn’t so horny for me.”

Ice sufficiently broken, it wasn’t long before disaster struck: Her cell phone rang in the middle of the audition.

“It was the worst thing that could have possibly happened,” she says with a laugh. “I answered it and improvised it as part of the scene, but then I had to pretend like it wasn’t continually vibrating as my friend Patrick kept calling. He basically was like, girl, what the f is going on? He thought I’d lost my mind.”

Her phone decorum must have impressed because Hahn was cast as Michelle, one of leading lady Andie Anderson’s fellow editors at Composure magazine. The flick filmed in Toronto which, on top of marking the actress’ first trip out of the country, provided a set experience that practically scrapbooks itself (How To: Scrapbook Your Very First Movie Role). The young actors were set up at a fancy hotel and, without the proliferation of smartphones to provide entertainment between takes, spent their downtime gossiping and cracking jokes. For Hahn, it all seemed impossibly fabulous.

“It felt like such a big budget movie to me,” she recalls. “Kate Hudson is a goddess and her star was crazy on the rise — I couldn’t believe I was getting to work with her. Shalom Harlow was this gorgeous model who would come into the hair studio I was working at in L.A., so the first time I met her I was like, ‘Oh, I totally took your coat once.’ She was kind enough to pretend to remember me.”

The whole experience seems steeped in mythology for Hahn, who at this point in her career likely wouldn’t blink twice at studio luxuries — the woman has an Emmy nom, after all. (She describes the flick’s red carpet in hilariously Hahn fashion as her “pumpkin-at-midnight” saga, complete with a broken heel and a publicist kind enough to run back to her house to grab a new pair of whatever she could find.)

Even though she has gone on to play far more substantive or meaningful-on-paper roles, like starring gigs on Transparent and I Love Dick, or singlehandedly carrying Bad Moms (the original and the sequel), her turn in How to Lose a Guy in 10 Days has stuck in the hearts and minds of so many fans. Michelle’s romantic transgressions — trying to move in with someone she’s been dating for a handful of days, among others — were hilarious and most everyone would be lying if they said a few of her habits didn’t ring true.

While Hahn can safely say she wasn’t a full-on lovesick puppy, she admits she didn’t have to stretch too far to play her: “I definitely have a Michelle.”

But besides setting up Andie’s dating rouse — possibly the most legendary of all the romantic comedy schticks — Hahn’s Michelle nabbed many of the movie’s best moments. Any discussion of How to Lose a Guy in 10 Days would be completely void without a loving tribute to her Fake Therapist. From the cult-like smock to the absurdly oversized glasses, she was a walking one-liner (“Benjamin, this is a safe space”).

“I wanted some sort of absurd disguise that was so clearly like, what are you doing,” she says of putting together the scene. “One of my personal favorite moments from that day was when Kate has to wipe her underarm sweat with the tissues. And McConaughey was so game — I remember it being hard to get through watching the two of them because they were really killing me.”

How to Lose a Guy in 10 Days (2003)
Credit: Everett Collection

When the movie finally hit theaters it did so with unbridled success, taking the top spot at the box office (during a pre-Valentine’s Day weekend) and eventually going on to make $177 million. It was 2003, the heyday of romantic comedies — that year alone saw the release of Love, Actually, Something’s Gotta Give, Just Married, and Under the Tuscan Sun. Before franchises and sequels and all things Marvel dominated pop culture, people ran to see these movies. It was, arguably, the last truly great romantic comedy.

For Hahn, the win (both box office and word-of-mouth) put her on the Hollywood map. She credits How to Lose a Guy in 10 Days with opening up audition rooms and giving her access to meetings with directors as well as providing a teaching moment about the business side of the industry.

“I remember someone congratulating me on Monday morning [after the release] and I was like, for what?” she says. “It never occurred to me to check returns. It was interesting to have people congratulate you on how well something had done because that had never been a topic of conversation for me before.”

It also gave the actress a fantastic cadre of stories to share with the flick’s many fans and a piece of the nostalgia-industrial complex to call her own. And we mean that in a literal sense: There’s a How to Lose a Guy in 10 Days board game — complete with her face on a chip — that she says will live in her garage “forever and ever.”

But the movie’s true legacy is a reminder of the good old days when romantic comedies were something to aspire to — for both the viewer and the actor. It had that nearly-perfect combination of sincere, tear-worthy scenes — Ben and Andie’s mutual shower in Staten Island has to be cemented in some sort of romance history book — that left viewers starry-eyed, but it wasn’t afraid to lean in hard to the classic (and cheesy) tropes. Take Andie’s job as a “columnist” for “Composure magazine” or even the Bet-with-a-capital-B that the entire meet-cute was hinged upon: These were completely absurd plot points and yet we wouldn’t change a thing about them.

After all, if Andie hadn’t had the unrealistic job that millions of young writers aspire to, we would still be fumbling around searching for the answers to age-old questions like How To Feng Shui Your Apartment and How To Talk Your Way Out of a Ticket. Or, Hahn’s personal fave, How To Bring Peace to Tajikistan.

“It’s 2018” she laughs. “In these trying times, you have to do what you can for Tajikistan.”

How to Lose a Guy in 10 Days
  • Movie
  • 112 minutes