Cute but geeky high-school student Samantha Martin (Hilary Duff) is knocked off her feet by her father's untimely death, which leaves his diner and Samantha's well-being in the care of Fiona (Jennifer Coolidge), Sam's thoroughly wicked stepmother. Not one to take on such menial tasks as dishwashing and mopping floors, Fiona exploits Sam's dependence as a method of hoisting any dirty work off her own shoulders. School is hardly a break for Samantha, particularly when Shelby (Julie Gonzalo) is around; spoiled, wealthy, and popular, Shelby treats Samantha nearly as badly as Fiona does. Samantha's life is irrevocably changed, however, by two events: a makeover of epic proportions and a sudden electronic correspondence with a mysterious young man. Due to a misplaced cell phone and a series of fateful coincidences, Samantha and her Prince Charming develop a romance through text messages and e-mails, and ultimately promise to meet face-to-face at the biggest school dance of the year. Of course, getting there doesn't go smoothly, and Samantha may miss her chance to meet her dream date -- none other than Austin (Chad Michael Murray), the most popular boy in school.