Sam (Hilary Duff), a teenager in California, is obliged to work as a janitor and dishwasher in the diner of her stepmother (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 Sam 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.