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.
This self-destructive binge would have continued if not for the historical advent of Prohibition. Fitzgerald here inserts a deft portrayal of a historical period that impacts his character in a meaningful way. The fact that Amory would have continued with his drinking without Prohibition indicates, however, the extent to which he could not find relief. The doomed affair still torments him.
His heartbreak does, however, allow him to throw off the job that he hated, that he kept only for his dream of life with Rosalind. Amory had become the "spiritually married man" that he so contemptuously describes in the final pages of the novel. By terminating their affair, Rosalind saves Amory from the sad fate he later decries. Yet it also shows the extent to which he loved her. He would have endured the job far longer--perhaps indefinitely--if it had meant that they could continue being together. Love dominated, or blinded, all other aspects of Amory's character, and it alone held meaning for him during that time. In losing love, he could go on to try to find himself again. It does not seem accidental that Amory recovers his wits through a friendship with Mrs. Lawrence, an older woman whom he does not love.
The conversations between Amory and Tom attack both the writers of their time, for being mediocre, and the critics of their time, for being too vicious. The upshot of these conversations seems to be that something better will come along. Amory's decision to write a poem despite his vow not to write, suggests that he is somehow apart from this mediocrity.
Amory's life continues to fall apart with Tom's departure, and he seeks the last friend he has left, Darcy. Just missing Darcy, however, he finds a romance with Eleanor that appears to be a truer romance than the one he shared with Rosalind.