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In The Far Side of Paradise, a highly acclaimed and authoritative biography of Fitzgerald, Arthur Mizener colors the conjugal relation between F. Scott Fitzgerald and Zelda as love. However, Fitzgerald implicates the impossibility of it in his autobiographical novel Tender Is the Night. In the novel, not only the marital relationship between Dick and Nicole but the illicit one between Dick and Rosemary altogether fail. This essay explores how such an impossible sexual relationship relates to Fitzgerald’s own innermost struggle to promote masculinity within his gender consciousness. This essay compares the two texts, The Far Side of Paradise and Tender Is the Night, in order to infer male anxiety from the crisis of masculinity and subsequent gender politics dissolving it. Additionally, this essay refers to Renata Salecl’s psychoanalytic explanation of ‘doubling’, a re-appropriation of Jacques Lacan’s idea of sexuation, as a way of elucidating Dick’s choice not to advance his passionate relationship with Rosemary. This study would allow us to see that Tender Is the Night provides questionable fantasy that Dick’s phallic potency can remain intact or be regained properly if only Nicole does not exist. Also, this study would shed light on how Dick’s self-control evading a passionate but perilous relationship with Rosemary arises from his anxiety that his manhood might be lost by the imagined overwhelming enjoyment from the relation. This essay helps us understand that Fitzgerald was actually engaged in his contemporary male anxiety and fantasy within and without his literature.