‘How to Lose a Guy in 10 Days’: Still Winning After 20 Years

In celebration of its 20th anniversary, assistant A&E editor Angela Ramirez highlights the best of the 2003 rom-com “How to Lose a Guy in 10 Days.”

Love ferns, “Bullshit” and Krull the Warrior King.

“How to Lose a Guy in 10 Days” turned 20 on Feb. 7 this year — a sobering milestone for the timeless film. 

Matthew McConaughey and Kate Hudson starred in what can only be referred to as one of the best rom-coms of all time. Reasons include, but are not limited to, the undeniable charisma of the lead couple and the dress. You know the one.

Despite the film’s predictable plot and cringeworthy one-liners — mostly from McConaughey — it still holds up as a classic. Of all the straight, white couples of early 2000s rom-coms, the 2003 film cements its place as one of the most iconic.

Hudson stars as Andie Anderson, a sharp young journalist who works at Composure — a women’s magazine based in New York City. She’s known as the resident “how-to” columnist, writing articles on dating advice.

On their way to work, Andie and her friend Michelle (Kathryn Hahn) discuss romantic troubles. Michelle recounts the issues within her recent breakup, which inspires Andie for a pitch idea for her editor — a how-to column of “don’ts” for a relationship, which her editor coins as “How to: Lose a guy in 10 days.” 

Benjamin Barry, a city boy version of McConaughey, is an executive at an advertising company. After his boss accuses him of misunderstanding women, Barry engages in a romantic bet, in which he has 10 days to make a woman fall in love with him if he wants to secure a career-defining business deal. 

Despite oozing on-screen chemistry, the pair’s 10-year age gap is impossible to ignore. While some find the gap excusable, the age difference, for some, continues to leave a sour note on the tongues of today’s viewers. 

The pair’s relationship starts off sweet, with Barry and Andie piquing each others’ interests. But as the days dwindle, the duo’s competitiveness takes over. 

Andie relentlessly delivers red flag after red flag, giving Ben multiple opportunities to call it off. She Photoshops an album with what their two children would look like, purchases a dog — which Ben ends up taking care of — and practically moves into his apartment mere days into their relationship. 

Notably, the supporting actors in the film provide some of the most hilarious moments. Ben’s workplace buddies Tony (Adam Goldberg) and Thayer (Thomas Lennon) have a plethora of one-liners that make up for Andie’s more cringeworthy moments. 

In one scene, Ben, Tony and Thayer gathered around a purse that Andie (purposefully) left at Ben’s apartment the night prior. 

“Well, it’s hardly a purse, dude, it’s more like a clutch or something,” Tony says to Ben.

“Guys, a woman’s purse, alright, it’s her secret source of power. Alright?” Ben replies to Tony, as Thayer looks at the pair confusingly. “There are many dark and dangerous things in there that we, the male species, should know nothing about.”

The film’s jokes range from unbearably unfunny to satisfactorily silly — offering “okay, that was a good one,” moments in-between cringes.

Like any other rom-com of the aughts, “How to Lose a Guy in 10 Days” has its fair share of quotable scenes, but the most notable is Andie’s rendition of “You’re So Vain” by Carly Simon. Recently, the song gained traction on TikTok, with over 17,000 videos posted with a clip of Andie’s rendition.

“And all the girls dreamed that they’d be Ben’s partner, they’d be Ben’s partner,” she sings to him.

In the season of post-Valentine’s blues, there’s very few films that suffice in the grand scheme of feel-good romances — “How to Lose a Guy in 10 Days” still reigns supreme in this category.

The film is available on Paramount+ and Amazon Prime Video with subscriptions.

Featured image courtesy of Paramount Pictures

Angela Ramirez

Angela Ramirez