Lola Cep (LINDSAY LOHAN) is a 15-year-old who thinks her life is ruined when her single mom, Karen (GLENNE HEADLY), moves her and her younger sisters from Manhattan to the suburbs of Delwood, New Jersey. Her only point of happiness is with her undying fan love for Stu Wolff (ADAM GARCIA), the lead singer of the rock 'n roll band Sidarthur.
Things look up when she meets fellow diehard fan Ella Gerard (ALISON PILL) on her first day at school, and catches sight of local hunk Sam (ELI MARIENTHAL). Yet, not everyone is so friendly, with rich girl Carla Santini (MEGAN FOX) leading a pack of high school snobs. She and Lola immediately clash, particularly when both compete for the lead in an updated version of Pygmalion to be directed by the school's drama teacher, Miss Baggoli (CAROL KANE).
When Lola learns that Sidarthur has announced they're breaking up, however, she thinks her life has gone into yet another tailspin. After Carla announces that she'll be attending their last performance and a post-concert party, Lola lies that she and Ella will also be going. Not wanting to use her father, Calum (TOM McCAMUS), for help, Lola tries to score tickets for the concert and party, all while dealing with Carla and rehearsing for her big debut in the school's play.