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In F. Scott Fitzgerald’s debut novel, This Side of Paradise, he depicts the grand scene of Jazz Age indulgence while also acknowledging its potential crisis. Hedonism could not heal the trauma of the First World War on American youth; thus, Fitzgerald seeks a new value to guide people out of confusion. In the 1920s, existentialism was not popular in America, but the author’s exploration of human value begins to take shape in this novel. From the perspective of Jean-Paul Sartre’s existentialism, this paper attempts to analyze the protagonist’s transcendence in his growth. After four reflections, the protagonist, Amory, experiences an epiphany and develops a state of being for itself. Examining this novel from an existential perspective enables us to reconsider Fitzgerald’s artistic intentions and recognize that his work explores more than just the disillusionment and confusion of the American Dream; it also contains aspects of optimism.