David, a struggling comedy writer fresh off from breaking up with his boyfriend, moves from New York City to Sacramento to help his sick mother. Living with his conservative father and much-younger sisters for the first time in ten years, he feels like a stranger in his childhood home. As his mother’s health declines, David frantically tries to extract meaning from this horrible experience and convince everyone (including himself) that he's "doing okay.”

At an elite, old-fashioned boarding school in New England, a passionate English teacher inspires his students to rebel against convention and seize the potential of every day, courting the disdain of the stern headmaster.