Hilary Duff never actually went to high school, for a start.
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.