Amory decides to treat his pain with alcohol and proceeds to get thoroughly drunk in the bar of a club. He wakes up in a hotel room at the club and starts drinking again. He bemoans the loss of his love and heads out to the town to carouse again in a flurry of parties, but he tells nobody of his misery. Amory heads to his work and announces to his boss that he is quitting and that he hated the meaninglessness of his job.
Four days later, a worn and exhausted Amory returns to his apartment. He explains to the inquisitive Tom that he had been beaten by all kinds of people. Tom in turn explains that Alec has moved out of the apartment to return home and that they might not be able to afford the rent themselves, but they do not leave, agreeing instead to live frugally. Amory gathers all his love letters and mementos of Rosalind, buries them in his trunk and sets out again on his debauch, leaving Tom behind.
After three weeks of this self-destructive alcoholic convalescence, Amory is stopped short by the institution of Prohibition, which makes booze far more difficult to find. Amory accepts the end of this phase without regret; he settles down and begins to read voraciously. He gets in touch with a friend of Monsignor Darcy's, Mrs. Lawrence, and she re-ignites his interest in life.
Still bored and feeling old, however, Amory attacks Tom for the cynicism of the review column Tom writes in the scholarly magazine, "The New Democracy." Amory explains that he himself will not write until his ideas clarify, and that he will never love again the way he loved Rosalind. Tom continues to rail against the writers of the day for being so mediocre, and insists that many of their names will not survive at all.
But Amory does try to write a short piece about his lost youth. Then Tom is forced to move out of the apartment to go take care of his mother, and Amory decides to go to Washington to visit Darcy. Not finding Darcy there, Amory goes to stay with an uncle in Maryland. There, he meets Eleanor.
Amory seeks to heal, or at least to forget, his broken heart by going on a three-week bender. He tells nobody of his troubles as he loses himself night after night in an alcoholic haze, an action that emphasizes the private nature of his loss. Amory no longer feels emotionless, but rather must drink to quell his powerful emotions. His decision to hide the love letters supports the privacy of his loss and his desire to bury his pain from sight.