Why Matthew McConaughey Almost Lost How to Lose a Guy Role

Kate Hudson may have tried and failed to lose a guy in 10 days, but she succeeded in cementing her status as one of Hollywood’s rom-com queens.

No bulls–t, it really has been 20 years since How to Lose a Guy in 10 Days premiered in theaters on Feb. 7, 2003. And two decades later, audiences still can’t get enough of palplable chemistry and playful banter between a then 23-year-old Hudson, fresh off her Golden Globe win for her breakout performance in Almost Famous, and Matthew McConaughey, 33, and fresh off from waltzing off with Jennifer Lopez in The Wedding Planner, with the movie going on to become a classic rom-com for the ages.

But before moviegoers even had a chance to fall for the love story of advice columnist Andie Anderson (Hudson) and advertising executive Ben Barry (McConaughey)—both of whom are entering their relationship with the ill intent of winning a bet at their respective workplaces—director Donald Petrie and his production team had one very big problem to solve: The ending.

In one early version of the draft, Ben finds out about Andie’s deception first, so “he makes her life miserable at the party, embarrassing her and you hated him,” Petrie exclusively told E! News. “So in the next version we said, ‘Okay, well, let’s have her find out first,’ and she found out first and made his life miserable and hated her.”

The solution ultimately came from an unexpected source: Comedy writer Tim Herilhey, who is mostly known for penning beloved Adam Sandler vehicles such as Billy Madison and Big Daddy.

“He did a brilliant job,” Petrie recalled, “Because if you look heavily at that scene, they are each finding out about the other at exactly the same time. And thus, they are each acting out on each other simultaneously. It’s always a fun push-and-pull between these two characters that really made it so wonderful.”

Given that Andie is doing everything in her power to drive Benjamin away, while he’s wooing her in order to land a major account at his firm, Petrie said there were constantly conversations on set about how to make sure viewers would still root for the characters, both as individuals and as a couple. And the filmmaker said he knew “pretty much from the get-go” that he had something special with the pairing of Hudson and McConaughey, whom he credited for selling the premise.

“In the scene where Ben has first encountered the craziness that Andie is putting on him, he says, ‘I don’t get it. What happened to this wonderful girl who was smart?’ You can tell he really likes her,” explained Petrie. “He’s not just doing this for the bet. And she does the same thing. She drives him crazy, she names his penis Princess Sofia! But then she gets on that elevator having feeling like, ‘I’ve done it,’ but immediately, she feels sad about that and that she really likes this guy. They really have a great connection, so we made sure that all along, even though they’re sparring, these two people really genuinely care for each other.”

So go water your love fern before you let it die, frost yourself and then dive into these behind-the-scenes secrets about How to Lose a Guy in 10 Days in honor of its 20th anniversary, including how Hudson fought for McConaughey to be cast:

1. Gwyneth Paltrow was initially attached to star, with Mike Newell set to direct. However, the director’s inability to “commit to a date” led Paltrow to leave the project to film A View From the Top, producer Lynda Obst told Entertainment Weekly.

2. Kate Hudson’s star-making turn in Almost Famous, which netted her a Golden Globe, landed her the part of Andie Anderson and she was already cast when Donald Petrie signed on as director. But it wasn’t such an easy task to find her leading man, with Petrie telling E! News casting Benjamin Barry was “the most difficult part” of the movie.

“Because in some ways and in every iteration of the script, it’s her movie,” he explained. “Usually, a big star doesn’t want to be second fiddle to the girl. That’s just fact. Kate was there through the casting, she read with everybody. And a lot of it was not just the reading, but, ‘Okay, how are you getting along in the room? Is this somebody you’re going to want to be on a set with for all this time? And is this somebody you think is going to give as much as they get?’ Because it’s a joust.”

3. Initially, the studio had a different actor in mind, though Hudson and Petrie felt he was too comedic for the part. So, when they did the screen test, Petrie picked three romantic scenes to gauge the pair’s chemistry.

“Are he and Kate going to have romance? Is there going to be a physical attraction there?” he recalled wondering. “And at the end of that, when we all watched the results with Paramount, they were like, ‘Oh okay, we can do that!’ And we went, ‘Really? It just kind of lays there.’”

4. So how did Matthew McConaughey ultimately land the part? Hudson advocated for him in a meeting with the studio, who was still championing the other actor (whom Petrie declined to name).

“I will never forget it because Kate was wonderful and gave a very erudite and yet heartfelt argument why that was the wrong choice,” Petrie recalled. “And even then, the studio put up, ‘Well, I guess we’ll just forget about this picture. We’ll do something else instead,’ thinking Kate would blink. Kate didn’t blink. She went, ‘You’re right, we’ll just do something else.’”

Finally, when the studio executive asked Hudson who she believed should be cast, “we pulled out the old list,” Petrie explained, “and Kate went right to Matthew McConaughey. The rest is history.”

5. However, Petrie admitted he was “even unsure” about casting McConaughey at first. “I think we all were, only in that he was 10 years older than Kate,” he explained of the age gap between The Wedding Planner star and Hudson.

And there was one other concern regarding the native Texan playing a hot-shot New York advertising executive, Petrie explained, “so I immediately had them write into the script that his father was in the Navy, his mother was Southern and they moved around a lot.”

6. Hudson spent a day shadowing Vogue’s editor-in-chief Anna Wintour after landing the role of an ambitious magazine columnist. “I tore out all of these how-tos in Cosmo and Glamour,” Hudson detailed to EW of preparing to play Andie. “Those are the kind of things that I skip over.”

7. The movie is based on a short cartoon book of the same name by Michele Alexander and Jeannie Long. And Andie’s two work BFFs Michele and Jeannie, played by Kathryn Hahn and Annie Parisse, were named after the authors.

8. Costume designer Karen Patch created the iconic yellow slip dress Andie wears to the climactic ball and designed it specifically to highlight the diamond necklace she wears in the scene. And Petrie immediately knew the gown would need a major moment as soon as Hudson walked out in the silk number.

“Everybody on the set went, ‘Wow!’” he recalled. “Seeing that the back had that scoop, I said to Kate, ‘When he first sees you, you have to do the full turn,’ which she does at the top of the steps. It’s such an absolutely marvelous dress.”

9. That necklace, the “Isadora Diamond” named after Isadora Duncan and housing a 80-carat yellow diamond in its center, was designed by Harry Winston and is worth $6 million. “It was yummy,” Hudson told E! News of rocking that, well, rock. “It was gorgeous. Also, it was terrifying!”

10. When it came to Andie’s style for the rest of the movie, Patch explained to CNN, “I wanted to use various designers to make it more real, as opposed to me designing them.” The costumer turned to Yves Saint Laurent, Prada, Marni, Narciso Rodriguez and Marc Jacobs to assemble the stylish writer’s wardrobe.

11. Explaining that he “loves to work in sneaky ways to keep things fresh and in the moment,” Petrie was a big advocate of his actors improvising in scenes.

“I’m going to Kate and saying, ‘Hey, see if you can get him to do this?’” he shared. “And I’m going to Matthew and telling him, ‘See if you can get her to do that,’ but you’re in opposites, so they are each given an intention that the other one is going to thwart.”

One shining example can be found in the scene where Andie surprised Benjamin by bringing a dog to his office. “I was standing with Kate and saw Matthew across the room looking at his reflection and fixing his hair,” Petrie recalled. “I turned to Kate and said, ‘Hey, it’s not in the script, but somewhere in the scene just start kissing him and try to mess his hair up as much as you can.’ And immediately Kate’s so excited about the scene, she’s got this secret.”

Rather than call cut over the unexpected gesture, McConaughey “went with it and I knew that at any given time that I could throw stuff at these two actors and they would just go with it,” Petrie said.

12. Hudson also ad-libbed many of the lines when Andie crashes Ben’s boys’ night, including making McConaughey blow his nose, throwing the platter of veggies and, of course, pointing out that he let their love fern die. “She could have played that rather seriously, but she just went to town with it,” gushed Petrie. “It’s subtle stuff but you see it all.”

13. Speaking of the iconic love fern, the plant played a special role at Petrie’s daughter’s wedding in November 2022. “Instead of the bouquet to throw, they brought a love fern!” he said with a laugh. “It wouldn’t surprise me at all if on Valentine’s Day fern sales go way up!”

14. Fresh off her graduation from Yale acting school, Hahn was the first supporting actor to be cast in the film.

“You never cast the first person. You have to say, ‘Okay, that set the bar, let’s see who else is out there,’” Petrie said of the WandaVision star. “And three weeks later, we hadn’t found anyone to beat Kathryn Hahn and we went right back to the beginning.”

15. Hahn reflected on the casting process in an interview with EW, detailing her final audition with Hudson in front of Petrie and the studio. “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,” the Bad Moms actress revealed of her first meeting with Hudson.

16. After that awkward introduction, Hahn’s phone then rang during their read-through. “It was the worst thing that could have possibly happened,” she recalled. “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–k is going on?’ He thought I’d lost my mind.”

17. “That’s why I got a motorcycle, because of this script,” McConaughey revealed to E! News. “I wanted to get comfortable…because I’ve seen too many people ride motorcycles or ride a horse in films and I’m like, ‘You don’t really ride a horse. You don’t really ride a motorcycle.’”

18. While critics were mixed on the movie, Petrie didn’t pay attention to the reviews, especially after How to Lose a Guy in 10 Days was screened for a test audience.

“It’s known within the industry that 55 percent is average,” he explained. “In this case, I believe we got a 94 percent.” While he knew women of all ages would be drawn to the rom-com (which it did, earning a 99 rating from female audience members), it was the score from men that “was the crazy thing,” Petrie said.

“Men of all ages gave it an 89 of all ages, averaging out to the 94,” he continued. “So one of the things that I like the most about the outcome of this movie is it’s the ultimate chick flick for guys.”

19. Five years after How to Lose a Guy in 10 Days, Hudson and McConaughey reunited for another rom-com, Fool’s Gold. But Petrie said fans should never rule out a possible sequel: “Well, who knows?”

20. In fact, in 2019, it was reported that a TV adaptation was in the works at Quibi. Alas, the mobile-focused streaming platform shut down seven months after its debut in in April 2020.

How to Lose a Guy in 10 Days is streaming on Paramount Plus.