While petting with Isabelle, Amory hurts her neck with his shirt stud. They begin to argue, and Amory realizes that he really has no affection for her at all. Isabelle claims that Amory is too conceited. He breaks off his relationship with her. He returns to Princeton the next morning.

Having failed a math class the previous year, Amory arrives at Princeton early in September to take a tutoring class and a make-up exam. He knows that, should he fail the exam, he will forfeit his position on the Princetonian board as well as jeopardize much of his chance for success. However, he does not study and therefore fails. Rather than blame his own laziness, Amory feels that it was his destiny to fail. This failure has brought him back to the “fundamental” Amory that he once was.

At Thanksgiving, Amory’s father dies. Amory attends the funeral without emotion. He is more interested in hearing the conditions of the will and the state of his father’s finances. It seems that the late Mr. Blaine made several bad investments, and the family finances have been severely depleted. Beatrice has her own income, but much of this went to pay for medical expenses during her nervous breakdown. Beatrice speaks of investing heavily in railroad and street car stocks because she believes that people will not long stay in one place.

Before returning to Princeton, Amory spends part of the Christmas vacation with Monsignor Darcy in New York. Monsignor explains to Amory that he is more of a personage than a personality. A personality is active, always overriding whatever comes next. A personage collects experiences like medals. Amory has considered leaving college and joining the Lafayette Esquadrilles, an aviation company fighting in France, but Monsignor tells him that he has not given up enough on life to take that step. Amory has been given a clean start, and it is up to him to make the most of it. Monsignor Darcy continues to write advice to Amory after he returns to Princeton.

Amory and Fred Sloan meet two girls during a night on the town. Amory goes back with them to the girls’ apartment, where he hallucinates that a man, whom he believes is the devil, is watching him. He leaves the apartment but feels that the devil is still chasing him, or perhaps he is chasing the devil. When he returns to Princeton, Tom tells him that the previous night he had a dream that Amory is in trouble. Later, Tom looks at the window and starts. He tells Amory to look but Amory sees nothing. Tom says there was someone at the window looking at Amory. Amory then tells Tom about seeing the devil the night before.