When his shorts accidentally fall off in front of the entire school, RJ's boring life as Pinkerton's biggest loser is turned upside down. His dream girl is within reach, but when he attends her pool party, things get ugly.
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When the corrupt Student Government Association denies RJ's request for Computer Club funding, RJ decides to take on his popular nemesis, Max Owens, in the election to become Pinkerton's SGA President.
In an attempt to get closer to his dream girl, Jenny Swanson, RJ tries out for the school musical, "Vamp Side Story." When he lands the lead role opposite Jenny, things get too close for comfort and big problems arise.
In order to buy Jenny Swanson a gift for her Sweet 16, RJ gets a job helping the seductive swinger, Mrs. Robbins. Meanwhile, RJ's new work schedule takes a toll on his friendship with Miles, who searches for a new best friend
When Jenny becomes single, she surprises everyone by asking RJ to study with her. As RJ prepares for their study-date, a shocking discovery leaves him questioning if he should tell the truth, or grab Jenny on the rebound.
Following his dad's advice, RJ sets his sights on the new girl in school, only to learn that she's a member of the Purity Club. When Claire invites RJ to the Purity Party, RJ discovers that the Purity Club might not be so pure.
After lying to the jocks about his sexual progress with Claire, a worried RJ sets out to make his lie true. Meanwhile, Miles gets busted for spreading rumors, and the girl of his dreams challenges him to a fight.
When his parents leave for the weekend, they leave RJ in the care of a sexy babysitter. Miles decides to throw a party for the nerds, which rages out of control, bringing RJ and his babysitter closer.
When a hungover RJ gets caught taking aspirin in the Principal's office, he gets sent to detention, where he befriends a tough thug named Hamilton. Lily tries out for the cheerleading squad in hopes of winning RJ's attention.
To win back Jenny's friendship, RJ and Miles hatch a risky plan to steal the test answers in order to help her ace the big biology test. Later, Miles promises to provide these stolen answers to the entire class.
RJ and Miles set out to find dates for the Winter Formal. After numerous rejections, RJ decides to ask his best friend Lily. A stunning twist of fate forces RJ to decide between the girl of his dreams and doing the right thing.
As Lily lies in a hospital bed, a guilt-ridden RJ is torn between upholding his promise to spend the night with her, and a once-in-a-lifetime opportunity to attend the Winter Formal with the girl of his dreams.