Cher is a fashion obsessed popular and wealthy girl who's just hit the top of the high school social scene. Living with her father who makes $500 an hour she also has a best friend who is also extremely wealthy and claims to know how it is to be envied by others. Her ex step-brother comes home from college to visit and they frequently battered each other with insults. He constantly claims that her only future is pointed in the direction of the nearest mall.
Though she claims her selfishness is innocent she puts together a plan to play matchmaker to two of her teachers to lower their grading standards so she can increase her grades after receiving a very bad report card. When she notices how truly happy the two are after getting together she notices that she feels good and accomplished about the good deed she had done.
She decides the ultimate way to give back is to take an under privileged new student under wing and show her the ropes and mysteries in the popular scene. They give her a complete makeover and steer her in the direction of a wealthy music industry worker's son.
The plan backfires causing Cher's high level in the social pyramid to lower and the boy she tried to hook up with her student tries to hook up with her. After a few romantic mishaps, one involving a homosexual boy whom she misreads and then tries to unsuccessfully seduce.
Her student returns to her for help asking her to help her get her step-brother but Cher refuses stating that they are not right for each other. The two argue for a bit and when the girl leaves Cher is left alone to collect her thoughts on her experiences. She wonders why she should care if this girl and her step brother are together.
Cher decides to do some soul searching by going on a shopping spree by herself. It is then she realizes that she has feelings for her step brother Josh. They eventually confess their feelings for each other and share a tender kiss to confirm the feelings.