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.