16 Sweet Secrets About A Cinderella Story Revealed

Raise your hand if you used “Never let the fear of striking out keep you from playing the game” in your AIM profile in 2004.

16 years ago, A Cinderella Story hit theaters and while critics didn’t exactly fall head over heels in love with the modern update to the classic fairy tale, it was a sleeper hit at the box office, making over $70 million at the box office, and has developed a cult following over the years. (“Mmm…so moist!” still makes us laugh and cringe at the same time.)

Lizzie McGuire star Hilary Duff‘s legions of fans fell for the textual love story between her character, girl next door Sam Montgomery, and One Tree Hill star Chad Michael Murray‘s Austin Ames, and it turns out the young superstar was actually harboring a bit of a crush on her on-screen leading man. 

But did you know a beloved Harry Potter star almost took on the role of the popular high school quarterback before Murray signed on? 

Check out these 16 behind-the-scenes facts you might not know about A Cinderella Story, including how it factored into Duff’s infamous feud with Lindsay Lohan and more…

1. The film’s writer Leigh Dunlap revealed it took Duff, a major Disney star at the time, signing on to star in the film to ultimately get the movie made and lead to a bidding war.”

“I was actually approached by some producers to write a ‘modern take on Cinderella’ and went from there, Dunlap told Slayground. “It didn’t take long to write originally but it took forever to sell. There were several competing Cinderella projects at the time.”

2. Cinderella was Duff’s favorite fairy tale growing up and she signed on to do the movie after Mark Rosman, one of her favorite Lizzie McGuire directors, brought the script to her mom and manager, Susan Duff.

3. Harry Potter star Rupert Grint was reportedly set to star as Austin Ames, but had to drop out due to scheduling conflicts with the beloved franchise. 

4. Before filming, Murray took Duff out for a coffee “just to get to know her and work with her so we could create some sort of relationship between each other so it would be easier on set,” the One Tree Hill star explained to Black Film.

5. Years later, Duff admitted to having a crush on her older co-star, telling Cosmopolitan, “I definitely had a crush on him. We had a few kissing scenes in the movie and I remember feeling pretty nervous about that, but then we became friends and I wasn’t so nervous anymore.”

6. Before Murray signed on, Austin Ames didn’t have much of a backstory, with Murray suggesting the conflict between the popular jock and his father over following in his footsteps to play football at USC.

“I sat down and I talked to the producer and director and said, ‘Guys, we should really grow on this storyline. I think having two storylines meet in the middle with two people who aren’t happy that find each other and become happy, I think that that’s interesting,'” Murray told Black Film.

7. The film’s epic kiss in the rain at the end of the movie actually took place on the third day of production, with Duff telling People, “It was much better than my real first kiss, but like, probably way more awkward because there were 270 people watching, crew and stuff like that, and we also shot it on the third day of filming. Out of those three days, I’d only worked with Chad one day…and we actually practiced a little bit.”

8. Murray inadvertently found himself involved in the ongoing (and now iconic) feud that was going on between Duff and his Freaky Friday co-star Lindsay Lohan after their love triangle with Aaron Carter.

“She…got pissed off because I worked with Chad Michael Murray [on Cinderella] after she had worked with him,” Duff claimed to Blender at the time. “She called him up and said all these awful things about me, which she then repeated to the press.”

9. Duff reportedly banned Lohan from attending the premiere of A Cinderella Story.

10. The dress Sam wore to the masquerade ball ended up becoming an instant classic, with thousands of girls trying to recreate the look for their Sweet 16 celebrations or proms. But the dress was almost completely different.

“When we were first trying to figure out Sam’s dress for the ball, I was harkening back to the original Cinderella, using all of those colored layers with this iridescent blue fabrics like you’ve probably seen in the Disney cartoon, and it just didn’t work out,” costume designer Denise Wingate told Interview. “I wanted it to be this colorful thing but after we camera tested it, it ended up looking like a mish-mash. So we went for something more classic, almost like a wedding dress, and just this beautiful vision of white. It was a Monique Lhuillier dress and it ended up being perfect.”

11. Finding the perfect mask for the big scene was also a challenge, with Wingate telling the publication, “We made 12 different masks—there’s a lot of trial and error to get it right when you’re dealing with a statement outfit.”

12. In one of his first major roles, The Big Bang Theory‘s Simon Helberg played Terry, the school nerd who had a crush on Sam. 

13. Because she was allergic to the nail glue, Jennifer Coolidge had to have Fiona’s fake nails taped on every day. 

14. Then 15, Duff learned how to drive while filming the movie, with her acting coach Troy Rowland acting as her driving instructor.

15. Screenwriter Leigh Dunlap admitted it was “a very sad process” for her as the studio “hired a million screenwriters” to re-write the film. 

“It’s no fun to see what you’ve written destroyed and there’s no one involved who thinks the finished script was better than the original,” Dunlap told Slayground. “But that’s what the studio wanted and they ended up with a huge hit, so you can’t fault that.”

16. Following in Duff’s glass slippers, Selena Gomez went on to star in the first sequel, with Sofia Carson and Laura Marano starring in the next two follow-ups in the franchise. 

A Cinderella Story is available to stream on HBO Max.