Berke (BEN FOSTER) and Allison (MELISSA SAGEMILLER) were high school sweethearts until she realized the romantic sparks between them were gone and then decided to break up with him. He thought their love would last forever, is naturally devastated by this development, and can't accept being dumped, especially when he sees Allison moving on with her life and getting friendly with Striker (SHANE WEST), the handsome new student at their school who also just so happens to be a member of a popular boy band.
Berke's best friends, Felix (COLIN HANKS) and Dennis (SISQÓ), decide he needs to get over Allison and get on with his life, as do his parents Beverly (SWOOSIE KURTZ) and Frank (ED BEGLEY, JR.) who host a relationship TV talk show. Yet, Berke has decided he's not going to give up so easily and hopes to win Allison back.
He gets his chance when he learns that she and Striker are going to try out for the school's spring play, "A Midsummer Night's Rockin' Eve," a musical adaptation of one of Shakespeare's plays staged by Dr. Desmond Forrest-Oates (MARTIN SHORT), the school's pretentious and occasionally condescending drama teacher. Although he's not much of an actor or singer, Berke tries out for the play, receiving some coaching from Felix's sister, Kelly (KIRSTEN DUNST), an aspiring singer/songwriter who's also hoping to nab a part in the musical.
As Kelly helps Berke, and his friends try anything to get him over Allison, the student tries to juggle the demands of the play, being on the basketball team, and starting to fall for Kelly, all while dealing with Striker who obviously has it out for him.