15-year-old Mary (Lola) Steppe (Lindsay Lohan), desperate for attention, moves with her family from New York City to the suburbs of Dellwood, New Jersey, to her disapproval. Her self-centered attitude then gets a reality check as she begins to realize she must compete against the current popular girl in school, Carla Santini (Megan Fox). Lola befriends an unpopular girl named Ella Gerard as they both share a love for the fictional band Sidarthur (spelling as in script, however sometimes interpreted as Sidartha or Sid Arthur - possibly a play on Sid Vicious and Sidhartha), whose lead singer, Stu Wolf (Adam Garcia), Lola has a crush on, and Ella has a crush on Steve, the guitarist.
Lola tries out for the school play, a modern version of Pygmalion named "Eliza Rocks" because the teacher wanted to base it on a modern-day New Yorker with "modern, hip" music. After getting the part of Eliza over her brand-new enemy Carla, the resentment between the two grows. What comes next is an announcement over the radio that Sidarthur has broken up and that Stu Wolf does not ever want to work with the band again. Lola and Ella are devastated.
Lola and Carla end up challenging each other on the dancing machine after school at an arcade. While there, Carla reveals that she already has tickets to Sidarthur's sold-out farewell concert due to her father being Stu Wolf's lawyer (mentioned earlier in the movie) as a revenge against Lola. Lola lies to Carla that she and Ella have tickets, too, based on a connection of her mom's. Lola wins the dancing machine game and earns some respect from the others.
Lola tries to get tickets as well in order to upset Carla. Because she gets grounded and has no allowance, Lola asks Sam, a friend who kind of adores her to "borrow" Eliza's dress. He nearly gets caught when Miss Baggoli (the drama teacher) gives the performers a break from training and goes to the drama room, but she is distracted by Lola while Sam hides as a mannequin, behind a mirror, and eventually exits behind Miss Baggoli's back. Ella offers to pay for both of their tickets at first. After failing to obtain tickets legally, Ella and Lola take a train to New York City in order to buy tickets from a scalper. But things don't go as well as they thought.
Lola had left her bag behind the sink on the train, and so doesn't have enough money to pay the scalper for illegal tickets. They try to get in, but a bouncer stops them. They walk the streets trying to find Stu's after-show party, but Lola's dad, Calum Steppe and his dog is following them. He promises to back off, but he threatens to come in if he sees anything wrong. He tries to tail them from further away. They finally get in after finding Stu passed out in an alley and taking him to a diner, where he throws a doughnut at a police officer. Stu is taken to the station, where Ella finds out Lola lied about her father being dead. When they arrive at Stu's house, Ella is still angry, but when they are dressed in Stu's clothes and in his room, she forgives Lola and the two have some fun. Later, Lola and Carla see each other and Carla becomes upset. Lola tries to discuss Stu's music with him, but ends up confronting him with the fact that he is a drunk after he rambles the whole time giving silly answers.
When Lola and Ella return to school, they try to talk to Carla about the party, where they saw her and she freaked out. Carla and her posse pretend they never saw her and convince the whole school that she is a liar using their claims, the fact that her father, who Lola claimed was dead, is really alive, and that Lola's birth name is Mary. Carla repeats this at the rehearsal about the party, which causes Lola to become depressed and not show up at the big night. Ella talks to Lola about how much everyone depends on her and Lola agrees. At the play, Lola does her role well and her mother, who has been calling her Mary against Lola's request, finally tells her that she is a Lola.
After the play, Carla Santini is having a party when Stu turns up, trying to find Lola to return her bottlecap necklace. Carla lies to everyone by telling them that Stu came to see her. When he finds Lola, he tells her he's gone into alcohol rehab. Carla backs up, trying to hold back tears and falls into her fountain. Lola comes over and helps her up, and Carla smiles a little at Lola. Lola turns back to Stu, and the two dance, which fades into Sam and Lola dancing, and the last scene shown is Lola and Sam, kissing in front of a fountain in Carla's house
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