1. Hilary Duff was only 15 when she started filming the movie, while her co-star Chad Michael Murray was 22.
2. Duff was homeschooled from the third grade onwards (aged 8), in order to focus on her acting career, so did not have to worry about missing classes for the movie.
3. So despite playing a bullied “nerdy” high schooler in this movie, Duff never went to high school herself.
4. Simon Helberg (Howard from The Big Bang Theory) played the character of Terry, the school nerd. This was one of his first major movie roles.
5. Chad Michael Murray starred as the main character's love interest in both A Cinderella Story and Freaky Friday. Julie Gonzalo, who plays school bully Shelby Cummings in A Cinderella Story, was also in Freaky Friday with him.
6. Rupert Grint was allegedly offered the role of Austin Ames but filming for Prisoner of Azkaban clashed with the making of this movie.
7. Michael Murray's character was more one-dimensional in the original script. The backstory of his father wanting him to be a college football player was expanded at his suggestion.
8. Despite playing a popular jock character in the movie, Murray hated high school. "I hated high school. I absolutely detested high school. But what can I say? I was more the Sam than the Austin... half those people that said shit to me in high school, they're filling gas station pumps" he said in a 2004 interview.
9. In the original script the fairy godmother was a valley girl character, until Regina King came on board. The character of Rhonda was written for her.
10. Rather than being an evil stepmother type, Jennifer Coolidge and Duff were close on set.
11. Coolidge had to get to set much earlier than all the other actors because her makeup took so long to apply.
12. Duff’s screen name ends with the number 818 which is the area code for San Fernando Valley where the movie is set. Michael Murray's ends in 609, the area code for Princeton where both characters aspire to go to college.
14. The romantic kissing scene where the characters make out in the rain at the football game was filmed on the third day of shooting.
15. The scene had to be reshot many times because the rain had to hit a certain spot on Michael Murray's face.
16. The director Mark Rosman made the two actors make out in front of him in his trailer so they could practice kissing before filming the scene. Ew.
17. Duff has admitted to having a crush on her co-star while filming the movie.
18. The movie's director Mark Rosman also directed several episodes of Lizzie McGuire.
19. The opening of the movie uses the song "This Will Be (An Everlasting Love)" by Natalie Cole which is the same music used in the credits at the end of The Parent Trap.
20. Duff and her sister Haylie performed a cover of the song "Our Lips Are Sealed" for the movie soundtrack. The song featured on the sister’s favourite film Romy and Michele’s High School Reunion.
21. As a child Duff trained as a ballet dancer and while on set she taught one of the movie’s producers how to waltz.
22. Duff had never played baseball in her life before the film, so had to learn for the scene in the movie.
23. She also had to learn to rollerskate for the diner scenes and fell over a number of times while practicing.
24. The 15-year-old actress was learning to drive while filming and practiced driving between set locations with her dialogue coach Troy Rowland.
25. Rowland was hired as her acting coach when she started work on Lizzie Maguire because Disney Channel executives though she could not act, “I remember early on the Disney Channel [was] absolutely convinced that Hilary couldn’t act,” producer Susan Jansen explained in an interview with E! News.
26. Rowland worked with Duff on a number of movies including Cheaper by the Dozen and Agent Cody Banks.
27. Duff won the Kid's Choice award for favourite movie actress for her performance in the movie.