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.

With the last day of Rawley Summer Session comes bad news for Will, who learns that the funds for his scholarship have been withdrawn, and Bella, who must fight against the sale of her family's gas station and home. The gang hits the road with Bella, determined to find her mother, who after ten years of silence is the one person who can save the station. On the journey, after running into car trouble, Bella, Will, Hamilton, Jake, Scout and Sean find themselves stuck in a cabin overnight, where tempers collide between all. Bella's eventual meeting with her mother opens up possible truths to the past, while Jake's true identity finally comes to light.

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.

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 troublemaking upperclassman Gregor Ryder that lands him in deep trouble with Finn, and Hamilton and Jake find themselves in a confusing competition over a girl.

The approaching Rawley Summer Cotillion inspires Will to approach the girl of his dreams, Caroline Busse, but when she already has a date for the dance, he invites Bella to go with him, although both their eyes are distracted by others. Meanwhile, Scout tries to make the most of his evening with Paige, and Hamilton and Jake reveal secrets in an intimate moment.

Achieving his life-long goal of escaping the wrong side of the tracks, Will thought his life would be perfect once he began at Rawley Academy, but trying to reconcile his new life with his old ties tests his growing friendship with Scout. Scout and Bella test the waters of their own newly platonic relationship and the end of their love affair, but Scout's jealousy over an admirer leads to a bloody brawl. Meanwhile, Hamilton and Jake work though their own weird moments and find a common ground of friendship.

Rawley Academy, a prestigious New England boarding school, begins its summer session. Will Krudski arrives on his first day at Rawley Academy; a dream that he has been anticipating to fulfill. He meets his new rommmate, Scout Calhoun, and later they meet the dean's son, Hamilton Fleming. The camaraderie between Will and Scout is later jeopardized when Will confides in Scout that he cheated on his entrance exam by purchasing it on the Internet. After meeting the unconventional crew coach and literature professor, Finn, Will seems to be adjusting to his new surroundings just fine.

It's the weekend of the annual Rawley Regatta, the biggest race of the year for the crew team, but everyone's minds are distracted by the approaching Parent's Weekend. Scout is excited about introducing Bella to his dad, her real father, but she is more savvy to what the Senator's reaction may actually be. Meanwhile, Will reaches out to his own father, and Jake has to hide her new identity from her self-absorbed mother.