While Amory embraces Isabelle, his shirt-stud hurts her neck and leaves a mark. Out of this incident, a small argument erupts in which Isabelle accuses Amory of being completely egocentric. He realizes that they actually do not love each other and leaves quickly; the affair is over.
Having failed a course the semester before, Amory returns to school early to study and take a make-up exam. But even though failing the make-up exam would disbar him from the newspaper and campus success, he does not study, and fails. Amory decides that he has conformed too much in striving for social success and believes that in failing the exam, he has rediscovered "the fundamental Amory."
Amory's father passes away and Amory attends the burial without emotion. What does interest him is the finances of his family, which are diminishing because of some bad investments.
Upon his return to the East, Amory visits Monsignor Darcy in New York. Darcy makes a distinction between "personalities" and "personages." The distinction is somewhat vague but the former, he explains, are a constant entity, while the latter gather experiences like medals, losing and gaining them with no effect. Darcy convinces Amory that Amory has given himself a new chance at life, and Amory leaves feeling renewed.
Amory disappears from the social scene at school and writes a scornful poem denouncing those who still participate. Kerry Holiday leaves school to enlist in the aviation corps called the Lafayette Escadrille, a chivalrous decision that Amory admires.
On one of his trips to New York, Amory and a drunken friend are out with two girls. The group heads back to one of the girls' apartments, where Amory thinks he sees a man with curling, fourteenth-century shoes staring at him: the devil. He flees to the alley and, in a rather psychedelic nightmare, believes he is being followed by the devil, or that he is following the devil. He falls to the ground, saying he wants "someone stupid," someone good, and sees the face of Dick Humbird. Amory continues to be plagued by what he perceives to be the horror around him. He returns to his room in Princeton, where Tom, too, sees the devil watching Amory. The two discuss it all night long.