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Samantha Montgomery (Hilary Duff) or "Sam", has a rough childhood with her father dying in an earthquake and a new stepmother with two awful daughters. But on the bright side, Sam has an awesome best friend named Carter (Dan Byrd) and an e-mail relationship with a guy named Nomad. One day, Sam gets an e-mail from her Nomad saying that he wants to meet her in the middle of the dance floor at their high school Halloween dance. She accepts the invitation and glides into the room wearing the best outfit ever. Her Nomad takes her outside where they share a romantic dance together and Sam realizes that her e-mail friend is the most popular guy in school, Austin Ames (Chad Michael Murray). She runs back to her stepmothers diner before she knows she went to the dance and drops her phone on the way. Austin finds it and starts a search for his Cinderella.
Samantha Montgomery (Hilary Duff), a teenager in California, is obliged to work as a janitor and dishwasher in the diner of her stepmother, Fiona (Jennifer Coolidge). After a cell phone mix-up, Sam begins an anonymous text-messaging and e-mail relationship with a boy. They agree to meet at a school dance, but when Samantha finds out that her secret pen pal is none other than Austin Ames (Chad Michael Murray), the cutest boy in school, she panics and looks for a way to make herself cooler.
Hilary Duff
Sam
Chad Michael Murray
Austin
Jennifer Coolidge
Fiona
Dan Byrd
Carter
Regina King
Rhonda
Julie Gonzalo
Shelby
Lin Shaye
Mrs. Wells
Madeline Zima
Brianna
Andrea Avery Ray
Gabriella
Mary Pat Gleason
Eleanor
Paul Rodriguez
Bobby
Whip Hubley
Sam's Dad
Kevin Kilner
Austin's Dad
Erica Hubbard
Madison
Simon Helberg
Terry
Bradley Joseph
David
JD Pardo
Ryan
Aimee-Lynn Chadwick
Astrid
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