If you want even more of a teen romantic comedy than Clueless, try this sweet, fairy-tale-inspired flick from 2004. Sam is unpopular at her high school and forced to work at the diner owned by her image-obsessed stepmother. Her two solaces are her dreams of attending Princeton and her secret chats with an online pen pal. What Sam doesn't know is that her online crush is Austin, the golden boy at her high school. When she gets the chance to meet him in person at a school dance, she seizes the opportunity, unknowingly opening the door to what could be either disaster or freedom at last.