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.