At eight-years-old, the blonde Samantha Montgomery (Hannah Robinson) lost her father to an earthquake, leaving her to live in an attic, while her stepmother Fiona (Jennifer Coolidge), and stepsisters, Gabriella (Andrea Avery Ray) and Brianna (Madeline Zima) take over her life. With popular kids Austin Ames (Chad Michael Murray), Shelby Cummings (Julie Gonzalo), and their crew, then her house family, the only escapes she has are the Diner Staff, her best friend Carter (Dan Byrd), and an on-line buddy, Nomad. They both go to North Valley High and dream of going to Princeton. They have a relationship that goes on through text messages and e-mails. He finally asks her to the Halloween dance, where they meet, and she finds out Austin Ames (Chad Michael Murray) is Nomad. Not knowing who his "Cinderella" is, he goes on one of the toughest quests ever, as Samantha's (Hilary Duff's) friends convince her to tell him. He finds out at a more than humiliating pep rally that Cincerella is "Diner Girl". She finally tells off her steps, and she manages to tell off Austin. At the end, they end up dating, going to Princeton, and she finds her dad's will, stating it leaves everything to Samantha. Happy Ever After? Who knows.