A Cinderella Story

Sam Montgomery (Hilary Duff) lived a semi-fairytale life with her widowed father Hal (Whip Hubley) when she was 8 years old in a suburb in California. Later, her father opened up a diner named after him and fell in love with a woman named Fiona (Jennifer Coolidge) who he later marries. One day, a falling support beam kills her father in the 1994 Northridge earthquake and leaves her with her plastic-surgery/salmon-obsessed stepmother and her two cruel stepsisters Brianna (Madeline Zima) and Gabriella (Andrea Avery). Eight years later, Sam is a straight-A student enduring her uncaring stepmother's wrath, who turned her father's cafe into a hot-pink hot spot and forces her to work as a diner girl. In addition to her family, Sam must deal with the popular girls at school, particularly the head cheerleader, led by Shelby Cummings (Julie Gonzalo). Sam confides in her best friend Carter (Dan Byrd) and her cyberspace pen pal, who wants to attend Princeton University with her. What she doesn't know is that her secret admirer turns out to be Austin Ames (Chad Michael Murray), the quarterback of the football team and the most popular student at school who is dating Shelby, who is obsessed with being popular.

As they text each other back and forth, Austin invites Sam to the Halloween Dance so they can meet face to face. Austin dumps Shelby a few hours before the dance. At the same time, Fiona forces Sam to work late at the diner that night until midnight. Rhonda (Regina King), Sam's mentor and friend at the diner, and Carter help Sam get to the dance, masquerading as Cinderella in a mask and Rhonda's wedding dress. She meets Austin in the middle of the dance floor and is at first put off by the fact that her pen pal is Austin Ames himself. He soon wins her over, and they move outside together. As they dance outside in a gazebo, they play 'Ten Questions' with Sam never revealing her identity. Meanwhile, Carter, disguised as Zorro, saves Shelby from David (Brad Bufanda), one of Austin's friends, from making a move on her.

Right before Austin is about to take off Sam's mask, her cell phone alarm goes off 15 minutes before midnight, warning her to run back to the diner before she's caught. She leaves Austin before he can figure out who she is. Austin and Sam are chosen as the Homecoming Prince and Princess, but apparently Cinderella is playing hard to get. Sam manages to find Carter, and they flee from the dance. On the way out, Sam accidentally drops her cell phone (which fills the role of the glass slipper). Austin, who has been following her, picks it up, determined to find out who she is.

Sam goes to school the next day to find Austin performing a school-wide search for his Cinderella. Sam is still feeling uncomfortable about revealing herself to Austin, who in turn is still searching obsessively. Sam tells Carter that if he tells Shelby he was her Zorro, she'll reveal herself to Austin. Carter agrees but after he tells Shelby, she rejects him. One afternoon, Sam's stepsisters find her emails while snooping around on her computer. After unsuccessfully trying to pass themselves off as Cinderella to Austin, they end up showing the emails to Shelby and her friends. The stepsisters make her believe Sam stole Austin on purpose, so Shelby puts together a cruel skit to perform at a football pep rally in order to humiliate Sam. The skit is performed in front of the whole school, as well as Austin's father who is present at the pep rally and has been pressuring Austin to attend college to play football at USC, his alma mater. Austin has never told his father he really wants to attend Princeton.

Hurt and humiliated, Sam goes back home and Fiona brings her a letter from Princeton saying that she was rejected. This is, in actuality, a fake letter as Fiona and the stepsisters threw out the real acceptance letter from Princeton, most likely so she wouldn't leave the diner. The next day at the diner, Brianna and Gabriella slam the door so a guitar with a photo of Elvis falls down (which they blame on Sam), ripping off the wallpaper and exposing a quote: "Never let the fear of striking out keep you from playing the game". Sam reads this aloud and decides she has had enough of her step-family and their abusive treatment. She quits working at the diner, tells Fiona that Fiona is through messing with her, and moves in with Rhonda, who, along with every other employee, also resigns. Because of this, all the customers leave early. The night of the big football game, Sam storms into the boys' locker room and confronts Austin, saying that she's fed up with his two different identities, one to her and one to his friends, "Waiting for you is like waiting for rain in this drought, useless and disappointing." Carter meets up with her at the school, and invites Sam to attend the football game with him. During a break in the game, Shelby confidently tells her fellow cheerleaders that she and Austin will soon be back together. In the last few moments of the game, while the team is huddled up before their next play, Austin sees Sam leaving and abandons the game. As he is running off the field, his father grabs him and asks him what he is doing, throwing away his dream like that, to which Austin replies that he is, in fact, throwing away his father's dream. He makes up with Sam and kisses her in public, and everyone starts clapping for them, much to the consternation of Shelby and the stepsisters. At the very same time it starts raining. Also the Fighting Frogs win the game even without Austin playing.

In the final scene of the movie, Sam finds her father's will hidden by Fiona. The will states that everything belongs to Sam. Sam uses this to sell Fiona's cars to pay for tuition, and after making a deal with the D.A., Fiona and the stepsisters work at her diner to pay her debt to soceity, under the watch of her new partner, Rhonda. Carter goes on to film a commercial and finally gets the girl, although the girl is not Shelby (who starts to flirt with him), but a cute pink haired punk girl who worked as a DJ and RJ in the college. Austin's father too comes around and accepts his son wanting to go to Princeton. Sam and Austin continue dating and both go to Princeton together.