Sam Montgomery (Hilary Duff) lives with her wicked step-mother (Stifler's mom) and step-sisters. She works at a 50s-style diner, dreams for better things and has a secret internet relationship with the most popular kid in school Austin (Chad Michael Murray from One Tree Hill). They agree to meet at a school dance, but she must be back home for midnight - instead of a glass slipper she accidentally leaves behind her phone, and her prince charming must track down his true love before its too late ... and he just moves on to the next girl in line.

Sam is outed by her ugly step-sisters at a high-school rally as the secret love interest, and Austin is embarrassed. 
  Back at the diner, fed up with life, she gets inspired from a quote on the wall and quits.
  At the big football game, its near the end of the 4th quarter and Sam decides to leave. Austin chases after her, abandoning the game. They kiss, and it starts raining.

Later, Sam finds her dad's real will - leaving the diner and everything to her, and not the step-mother. The cops pay a visit to the fraudsters, and they are forced to work at the diner as community service. The step-sisters find the real acceptance letter from Princeton in the trash.  The diner is restored, and Sam's friend Rhonda promoted to manager.

It ends with Sam and Austin sitting in a car, same place as the first scene, about to ride off to Princeton together.