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 roommate, 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.

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.