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The diner in which Samantha Montgomery (Hilary Duff) works, is located in Long Beach. The address is 4390 Atlantic Avenue, Long Beach, California. The diner is actually called "George's 50's Diner."
Rupert Grint won the role of Austin Ames, but had to drop out due to commitments to Harry Potter and the Prisoner of Azkaban (2004). The role of Austin Ames instead went to Chad Michael Murray.
Hilary Duff accepted the lead role because Charles Perrault's story "Cinderella" was her favorite fairy tale when she was growing up.
In preparation for her driving test, Hilary Duff drove herself between filming locations during principal photography for this movie.
Many characters have distinct color schemes: Samantha Montgomery and Austin Ames primarily wear blue, Fiona primarily wears pink, Brianna primarily wears green, and Gabriella primarily wears red. Almost all of these tie-in to the color schemes of their corresponding characters in Disney's Cinderella (1950).