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.

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

4. Because of the 10-year age-gap betwixt Hudson, 23, and Matthew McConaughey, 33, producers astir passed on The Wedding Planner star. "At archetypal we thought helium was excessively aged for her," Obst admitted to EW, earlier Hudson rationalized her then-husband Chris Robinson was 36 years old. 

5. The movie is based connected a abbreviated cartoon publication of the aforesaid sanction by Michele Alexander and Jeannie Long.

6. Andie's 2 enactment BFFs Michele and Jeannie, played by Kathryn Hahn and Annie Parisse, were named aft the authors. 

7. 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. 

8. That piece, 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!"

9. 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.

10. Director Donald Petrie encouraged his leads to improvise, explaining successful an interrogation with the BBC, "I'm precise sneaky arsenic a director. I'd spell implicit to Kate and say, 'OK, successful this adjacent take, don't archer Matthew, but bash this.' She would bash it. What's large is that, due to the fact that they're specified consummate professionals, they ne'er interruption character. They conscionable spell with it. They conscionable helping it. I ne'er accidental 'Cut!' astatine the extremity of a scene." 

11. One of those improvised scenes is erstwhile Andie jumps connected Ben and smothers him with kisses aft introducing him to Krull, their dog. This pb to a genuinely amazed absorption from McConaughey.

12. Most of Hudson's lines successful the country wherever Andie crashes Ben's boy's nighttime were besides unscripted, arsenic good arsenic the determination to propulsion the platter of veggies.

14. 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." 

15. There's an unexpected cameo from Katherine Heigl in the movie arsenic a screen exemplary for Composure, the mag Andie works for. 

16. "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 emergence a equine successful films and I'm like, 'You don't truly thrust a horse. You don't truly thrust a motorcycle.'"

17. Five years aft How to Lose a Guy successful 10 Days, Hudson and McConaughey reunited for different rom-com, Fool's Gold. 

18. In 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.