Berke (Ben Foster) and Allison (Melissa Sagemiller) are the original high school golden couple - they've been together for as long as anyone can remember. He's cute, she's gorgeous, it's perfect. Until Allison suddenly dumps him out of the blue and starts dating smug boy-band-wannabe Striker (Shane West).
Berke's got to get her back, and if it means swapping his basketball vest for a toga and humiliating himself in the school musical, then that's a price he's prepared to pay. His friends Dennis (SISQO) and Felix (Colin) have other plans. But while they're plotting to get Berke back in the dating game, they miss the cure that's right under their nose - Felix's little sister Kelly (Kirsten Dunst). Is she just helping Berke learn his lines or are there some other moves she wants to show him?