1. Gwyneth Paltrow was initially attached to star, with Mike Newell acceptable to direct. However, the director's inability to "commit to a date" led Paltrow to leave the task to movie A View From the Top, shaper Lynda Obst told Entertainment Weekly.

2. Kate Hudson's star-making crook in Almost Famous, which netted her a Golden Globe, landed her the portion of Andie Anderson and she was already formed erstwhile Donald Petrie signed connected arsenic director. But it wasn't specified an casual task to find her starring man, with Petrie telling E! News casting Benjamin Barry was "the astir hard part" of the movie.

"Because successful immoderate ways and successful each iteration of the script, it's her movie," helium explained. "Usually, a large prima doesn't privation to beryllium 2nd fiddle to the girl. That's conscionable fact. Kate was determination done the casting, she work with everybody. And a batch of it was not conscionable the reading, but, 'Okay, however are you getting on successful the room? Is this idiosyncratic you're going to privation to beryllium connected a acceptable with for each this time? And is this idiosyncratic you deliberation is going to springiness arsenic overmuch arsenic they get?' Because it's a joust."

3. Initially, the workplace had a antithetic histrion successful mind, though Hudson and Petrie felt helium was excessively comedic for the part. So, erstwhile they did the surface test, Petrie picked 3 romanticist scenes to gauge the pair's chemistry.

"Are helium and Kate going to person romance? Is determination going to beryllium a carnal attraction there?" helium recalled wondering. "And astatine the extremity of that, erstwhile we each watched the results with Paramount, they were like, 'Oh okay, we tin bash that!' And we went, 'Really? It conscionable benignant of lays there.'"

4. So however did Matthew McConaughey yet onshore the part? Hudson advocated for him successful a gathering with the studio, who was inactive championing the different histrion (whom Petrie declined to name). 

"I volition ne'er hide it due to the fact that Kate was fantastic and gave a precise erudite and yet heartfelt statement wherefore that was the incorrect choice," Petrie recalled. "And adjacent then, the workplace enactment up, ‘Well, I conjecture we'll conscionable hide astir this picture. We'll bash thing other instead,' reasoning Kate would blink. Kate didn't blink. She went, ‘You're right, we'll conscionable bash thing else.'"

Finally, erstwhile the workplace enforcement asked Hudson who she believed should beryllium cast, "we pulled retired the aged list," Petrie explained, "and Kate went close to Matthew McConaughey. The remainder is history."

5. However, Petrie admitted helium was "even unsure" astir casting McConaughey astatine first. "I deliberation we each were, lone successful that helium was 10 years older than Kate," helium explained of the property spread between The Wedding Planner star and Hudson.

And determination was 1 different concern regarding the autochthonal Texan playing a hot-shot New York advertizing executive, Petrie explained, "so I instantly had them constitute into the publication that his begetter was successful the Navy, his parent was Southern and they moved astir a lot." 

6.  Hudson spent a time shadowing Vogue's editor-in-chief Anna Wintour aft landing the relation of an ambitious mag columnist. "I tore retired each of these how-tos successful Cosmo and Glamour," Hudson elaborate to EW of preparing to play Andie. "Those are the benignant of things that I skip over."

7. The movie is based connected a abbreviated cartoon publication of the aforesaid sanction by Michele Alexander and Jeannie Long. And Andie's 2 enactment BFFs Michele and Jeannie, played by Kathryn Hahn and Annie Parisse, were named aft the authors.

8. Costume decorator Karen Patch created the iconic yellow slip formal Andie wears to the climactic shot and designed it specifically to item the diamond necklace she wears successful the scene. And Petrie instantly knew the gown would request a large infinitesimal arsenic soon arsenic Hudson walked retired successful the silk number. 

"Everybody connected the acceptable went, 'Wow!'" helium recalled. "Seeing that the backmost had that scoop, I said to Kate, 'When helium archetypal sees you, you person to bash the afloat turn,' which she does astatine the apical of the steps. It's specified an perfectly marvelous dress."

9. That necklace, the "Isadora Diamond" named aft Isadora Duncan and lodging a 80-carat yellowish diamond successful its center, was designed by Harry Winston and is worthy $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 benignant for the remainder of the movie, Patch explained to CNN, "I wanted to usage assorted designers to marque it much real, arsenic opposed to maine 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 helium "loves to enactment successful sneaky ways to support things caller and successful the moment," Petrie was a large advocator of his actors improvising successful scenes. 

"I'm going to Kate and saying, 'Hey, spot if you tin get him to bash this?'" helium shared. "And I'm going to Matthew and telling him, 'See if you tin get her to bash that,' but you're successful opposites, truthful they are each fixed an volition that the different 1 is going to thwart."

One shining illustration tin beryllium recovered successful the country wherever Andie amazed Benjamin by bringing a canine to his office. "I was lasting with Kate and saw Matthew crossed the country looking astatine his reflection and fixing his hair," Petrie recalled. "I turned to Kate and said, 'Hey, it's not successful the script, but determination successful the country conscionable commencement kissing him and effort to messiness his hairsbreadth up arsenic overmuch arsenic you can.' And instantly Kate's truthful excited astir the scene, she's got this secret."

Rather than call chopped implicit the unexpected gesture, McConaughey "went with it and I knew that astatine immoderate fixed clip that I could propulsion worldly astatine these 2 actors and they would conscionable spell with it," Petrie said. 

12. Hudson besides ad-libbed galore of the lines erstwhile Andie crashes Ben's boys' night, including making McConaughey stroke his nose, throwing the platter of veggies and, of course, pointing retired that helium fto their emotion fern die. "She could person played that alternatively seriously, but she conscionable went to municipality with it," gushed Petrie. "It's subtle worldly but you spot it all."

13. Speaking of the iconic emotion fern, the works played a peculiar relation astatine Petrie's daughter's wedding successful November 2022. "Instead of the bouquet to throw, they brought a emotion fern!" helium said with a laugh. "It wouldn't astonishment maine astatine each if connected Valentine's Day fern income spell mode up!"

14.  Fresh disconnected her graduation from Yale acting school, Hahn was the archetypal supporting histrion to beryllium formed successful the film.

"You ne'er formed the archetypal person. You person to say, 'Okay, that acceptable the bar, let's spot who other is retired there,'" Petrie said of the WandaVision star. "And 3 weeks later, we hadn't recovered anyone to bushed Kathryn Hahn and we went close backmost to the beginning."

15. Hahn reflected connected the casting process successful an interrogation with EW, detailing her last audition with Hudson successful beforehand of Petrie and the studio. "I was truthful nervous, I retrieve I broke the crystal by joking astir the horny summers astatine this theatre campy we had some been to erstwhile we were kids," the Bad Moms actress revealed of her archetypal gathering with Hudson.

16. After that awkward introduction, Hahn's telephone past rang during their read-through. "It was the worst happening that could person perchance happened," she recalled. "I answered it and improvised it arsenic portion of the scene, but past I had to unreal similar it wasn't continually vibrating arsenic my person Patrick kept calling. He fundamentally was like, 'Girl, what the f--k is going on?' He thought I'd mislaid my mind." 

17. "That's wherefore I got a motorcycle, due to the fact that of this script," McConaughey revealed to E! News. "I wanted to get comfortable...because I've seen excessively galore radical thrust motorcycles oregon thrust a equine successful films and I'm like, 'You don't truly thrust a horse. You don't truly thrust a motorcycle.'"

18. While critics were mixed connected the movie, Petrie didn't wage attraction to the reviews, particularly aft How to Lose a Guy successful 10 Days was screened for a trial audience. 

"It's known wrong the manufacture that 55 percent is average," helium explained. "In this case, I judge we got a 94 percent." While helium knew women of each ages would beryllium drawn to the rom-com (which it did, earning a 99 standing from pistillate assemblage members), it was the people from men that "was the brainsick thing," Petrie said. 

"Men of each ages gave it an 89 of each ages, averaging retired to the 94," helium continued. "So 1 of the things that I similar the astir astir the result of this movie is it's the eventual chick flick for guys."

19. Five years aft How to Lose a Guy successful 10 Days, Hudson and McConaughey reunited for different rom-com, Fool's Gold. But Petrie said fans should ne'er regularisation retired a imaginable sequel: "Well, who knows?"

20. In fact, successful 2019, it was reported that a TV adaptation was successful the works at Quibi. Alas, the mobile-focused streaming level unopen down 7 months aft its debut successful in April 2020.