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Many rom-com fans can likely agree that How to Lose a Guy in 10 Days wouldn’t be the same without Kate Hudson’s “Benny boo-boo” lines or her cover of “You’re So Vain.” She and Matthew McConaughey had an electric chemistry that made the movie one of the most iconic romantic comedies to this day. How to Lose a Guy even led Hudson and McConaughey to co-star in another film, Fool’s Gold, a few years later.

And yet, the earliest plans for How to Lose a Guy in 10 Days didn’t include Hudson as the leading lady. Here’s who was the first choice to play Andie Anderson and how the part ended up going to Hudson. Plus, how Hudson helped seal the deal on McConaughey.

Kate Hudson poses at the How to Lose a Guy in 10 Days press conference in 2003
Kate Hudson attends a ‘How to Lose a Guy in 10 Days’ press conference at the Four Seasons Hotel in Beverly Hills in 2003. | Vera Anderson/WireImage

‘How to Lose a Guy in 10 Days’ turns 20 years old

Feb. 7, 2023, marked the 20th anniversary of How to Lose a Guy in 10 Days. And though romantic comedies look a bit different today, the 2003 film is one of a few classics that are still popular. How to Lose a Guy even reached a younger audience in recent weeks, as Hudson’s cover of “You’re So Vain” became a viral sound on TikTok.

In How to Lose a Guy in 10 Days, Hudson plays an advice columnist named Andie Anderson. She plans to write an article called “How to Lose a Guy in 10 Days” and do everything that would drive a man away from a relationship. Then, Andie finds the subject of her article: McConaughey’s Benjamin Barry, an advertising executive working on a diamond jewelry campaign. Little does Andie know that Ben made a bet that he could make any woman fall in love with him in 10 days. She tries to push him away, he tries to bring her closer — and they fall in love for real.

Kate Hudson wasn’t the first choice to play Andie in ‘How to Lose a Guy in 10 Days’

Donald Petrie (Mystic Pizza, Miss Congeniality) directed How to Lose a Guy. However, the film was initially attached to director Mike Newell (Four Weddings and a Funeral). Meanwhile, Gwyneth Paltrow was supposed to star as Andie. But, as producer Lynda Obst revealed to Entertainment Weekly in 2003, Newell couldn’t “commit to a date.” Paltrow then moved on to another rom-com, View From the Top.

So, how did Hudson get considered for the role? It all had to do with a comedy-drama she starred in a few years prior: Almost Famous. In 2001, Hudson won a Golden Globe for Best Supporting Actress in a Motion Picture for Almost Famous. The producers of How to Lose a Guy knew they had to have her on board.

“At some point, [former Paramount president] Sherry Lansing and I, were both madly in love with [Kate Hudson],” Obst told Vanity Fair in a 20th-anniversary interview. “It’s clearly after Almost Famous. I just remember, we turned to each other like, ‘This has to be Kate. She’s hilarious.’ And so Kate got attached.”

Kate Hudson helped Matthew McConaughey land the role of Ben

After Hudson signed on, How to Lose a Guy had to find her co-star. Hudson and the producers considered several actors, including McConaughey. He had already been a hit in The Wedding Planner in 2001. Everyone agreed that McConaughey was the best candidate, but there was one concern: his age. Hudson was 23 at the time, while McConaughey was 33. The producers worried that McConaughey was too old for Hudson.

It was Hudson who ultimately convinced them to cast McConaughey. She used her then-husband, Chris Robinson, as proof that McConaughey’s age didn’t matter to her.

“I’m married to a 36-year-old, and it’s not like he’s ancient,” Hudson said at the time, per Entertainment Weekly.