Several times in the novel, Amory reflects on what has influenced his development most. The initial influence is his unconventional mother, Beatrice. He tries to correct her influence by trying to fit in and behave conventionally at school. He attends school in the Midwest, then boarding school, and finally Princeton, trying hard to fit in at each. When he is finally successful, he discovers an emptiness in conformity. Amory abandons conformity half-way through Princeton, and gets back on the path of rediscovering who he is.
From a very early age, Amory is both attracted to and repelled by romantic involvement with women. After several failed loves, and after the war, he falls deeply in love with Rosalind, and she with him. But, refusing to marry someone without great wealth, Rosalind breaks Amory's heart. He tries love again with Eleanor, and may have been happy with her, but feels that having had his heart broken, he is incapable of love. Finally, he abandons women as a source of inspiration. He lost himself in Rosalind and only finds himself again without her.
Though quite wealthy while growing up, because of his family's bad investments and his mother's dying bequeathment to the church, Amory finds himself penniless by the novel's end. Without his wealth to fall back on, Amory is forced to look harder for meaning in his life. He realizes that he hates poverty and even goes so far as to preach socialism, hoping that he might land himself on top if a revolution took place. With no money, Amory has to look deep within himself for guidance.