One of the novel’s key themes explores the role disillusionment plays in an individual’s coming of age, as Amory’s grandiose self-image and idealized notions of life give way to a more sober and realistic view of the world as he matures. In This Side of Paradise, Amory must learn to cope with the disappointment of not everything turning out according to his wishes and expectations.

Amory experiences his first sense of disappointment when he kisses Myra at the Minnehaha Club. Amory views his feelings for Myra as an adventure and enjoys the chase. However, once he kisses the girl, “[s]udden revulsion seized Amory, disgust, loathing for the whole incident. He desired frantically to be away, never to see Myra again, never to kiss anyone” (21). This image of extreme disappointment foreshadows similar experiences where Amory’s expectations and ideals do not live up to reality. Amory asks to go to prep school thinking it will be a satisfying experience for him, but he ultimately ends up “discouraged and imagined himself a pariah” (33). Amory misunderstands the purpose behind his education at St. Regis’ and uses the experience only to further his social ambitions. This propensity for disappointment and discontent follows him to Princeton.