The “winter dreams” of the story refer to the American Dream that Dexter comes to embody, but success brings a high cost, and social mobility restricts Dexter’s capacity for happiness. Dexter is from humble origins: his mother was an immigrant who constantly struggled with the language of her adopted homeland. The central irony of the story is that realizing the American Dream yields bleak rewards. For example, when Dexter was a young caddy, he dreamed about success and wealth and the happiness they would bring. When he finally beats T. A. Hedrick in a golf tournament, however, the triumph brings him little joy. Dexter is able to transcend middle-class inertia but, despite his tireless efforts to advance his fortunes, forced to accept that money cannot buy happiness.
Dexter has an ambiguous relationship with the bluebloods and idle rich who populate his social world. On one hand, he is proud of his self-made status and has no respect for the men for whom luxury and wealth were a given. Still, the men are emblems of a world to which Dexter wants to belong. In pursuing Judy, he is attempting to validate his claim as a bonafide member of the upper class. Dexter feels that he is a newer, stronger, and more praiseworthy version of the Mortimer Joneses of the world, but he still mimics the rich in gesture and appearance. He pays meticulous attention to his appearance, concerned with small details that only an outsider who was trying to disguise himself as a man of wealth would really notice. Dexter’s position in this world is precarious, and there is no room for error in appearance or etiquette. Through Dexter and the world of earned distinctions that he comes to represent, Fitzgerald exposes the hollowness that comes from the aggressive pursuit of the American Dream. Wealth and social status substitute for strong connections to people, eclipsing the possibility of happiness of emotional fulfillment.
Reality and fantasy prove to be constantly at odds with each other as Dexter and Judy search for stability and meaning in “Winter Dreams.” Dexter is the victim of his so-called winter dreams, adolescent fantasies that he is never able to fulfill. As he searches for happiness and love, he unwisely focuses his quest exclusively on Judy Jones, making her the sole object of his romantic projections. However, rather than provide fulfillment for Dexter, Judy and her displays of affection simply trigger more yearning. Dexter never sees Judy for who she really is; rather, he sees her as an ideal of womanhood and the embodiment of perfect love. Later, Judy reveals her self-serving nature when she confesses that she is breaking off relations with a man who has pursued her simply because he is not of adequate financial means. Dexter, still blinded by his idealistic view of Judy, cannot digest this information, because it suggests the reality of who Judy is.
Although Dexter recognizes the real threat of harm beneath Judy’s charm and beauty and tries to convince himself that he is no longer in love with her, he cannot fully divorce himself from the romantic, uncontrollable attachment he has to her. Ultimately, Dexter becomes the victim not of Judy’s fickle behavior but of his own stubborn ideals. Time and again, Dexter and Judy struggle with contradictions between reality and fantasy. On their first date, Dexter is disappointed that Judy appears in an average dress and, instead of the pomp and ritual he expected, blandly tells the maid that they are ready to eat. In their ambiguous and protracted courtship, Judy treats him with “interest . . . encouragement . . . malice . . . indifference . . . [and] contempt.” The reality of this relationship is bleak, but the idealistic vision of what it could be enables it to limp along.