A Cinderella Story (2004) is an update of the classic tale made famous by Disney's iconic animated version. This take on the story is transformed into a teen romantic comedy with Hilary Duff as a Cinderella-esque teen living with her father and not-so-nice stepmother. The "prince" is a popular football high school jock played by Chad Michael Murray.
As a nod to the times, the two meet online and become pen pals. Football player Austin Ames (Murray) disguises himself as a guy named "Nomad" and corresponds with Samantha Montgomery (Duff). The film starts with a flashback of a ten year Samantha, nicknamed Sam. Her widowed dad (Whip Hubley) runs a popular diner in suburban Los Angeles. Sam's dad marries a woman whose first priority is herself. Life with the self-absorbed Fiona (Jennifer Coolidge) is bearable until Sam's dad is killed during an earthquake. Fiona ends up with everything, including custody of Sam.
Flash forward to a now eighteen-year old Sam. She works - er, slaves - at the diner. She has to deal with an overbearing Fiona and her daughters from a previous marriage, Gabriella and Brianna. Adding to Sam's torment is her high school's head cheerleader, Shelby (Julie Gonzalo). Sam finds solace through an online friend known to her as "Nomad." She shares her dreams about going to Princeton and her hectic life at the diner with her "evil" stepmother. Austin - the real name of the popular high school football player known to Sam as "Nomad" - is unhappy with his life, which includes Shelby.
Sam's friends convince her to meet her friend at the school's Halloween dance. These same friends encourage her to ditch late night diner duty and go to the dance. A masked Sam discovered her friend is really Austin. The two go for a walk and get to know each other. Sam has to rush off to get back to the diner before Fiona comes back. In her haste, she drops her cell phone. Every girl in school claims to be the owner of this modern day "glass slipper."
Even after her identify is revealed, additional obstacles stand in the way of the budding romance between Austin and Sam. Her stepsisters and Shelby try to make her look bad, especially to Austin. The star jock faces problems of his own, namely standing up to his dad. A subplot involves Sam and her co-worker and friend, Rhonda (Regina King), trying to save her father's diner. Is there a happy ending to this Cinderella story? You'll have to see for yourself.