The feminine balance is thrown off with the arrival of Paige Bennett, a beautiful, sophisticated new student at Rawley Girls Academy who Bella likes in spite of herself. Paige is unabashedly in romantic pursuit of Scout, whom she's known since they were kids, and may be successful at turning his head away from his forbidden love. Meanwhile, Will has a run-in with a trouble-making upperclassman, Ryder Forrest that lands him in deep trouble with Finn, and Hamilton and Jake find themselves in a confusing competition over a girl.

Bella, Will and Scout find themselves in the crazy position of having to outsmart an evil upperclassman, Ryder, sweet-talk a cop while driving a stolen car, and retrieve a confessional letter before it destroys their lives. Meanwhile, Hamilton and Jake secretly go on their first official date, but with Jake in a dress, the sexual roles are confused as Hamilton tries to wear the pants in the couple.

Will finds himself in the enviable position of poetry tutor to the girl of his dreams, Caroline Busse, but his nightmare begins when he learns that an obnoxious upperclassman, Ryder, also has his eyes on the prize. Meanwhile, the surprise of a lifetime comes for Bella on her 16th birthday, and rumors fly about Hamilton and Jake's clandestine love affair.