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.
Fitzgerald uses similes throughout “Winter Dreams,” most notably at the beginning of the story, to make abstract notions, such as the frustrations of love and drive to succeed, more concrete. The similes also suggest the gulf that separates reality from the illusions the characters are subject to. In the first sentence of the story, we learn that, unlike Dexter, some of the caddies at the country club are “poor as sin.” As winter settles on Minnesota, snow covers the golf course “like the white lid of a box,” and the wind blows “cold as misery.” These similes, grimly preoccupied with gloomy notions of misery and poverty, set the tone for the unhappy tale that Fitzgerald is about to convey.
Similes help clarify the abstract idea of Dexter’s winter dreams. His visions of grandeur involve vague, half-formed hopes for success and wealth and the satisfaction he assumes will accompany them. Dexter is able to translate his dreams into reality. He becomes the self-professed richest young man in his part of the country and gets to face off in a round of golf with Mr. Hedrick, whom he easily beats. However, he is still dogged by the abstract—his struggle to find love and accept the responsibility of belonging to someone else. During his first fateful meeting with the adult Judy, his heart “turned over like the fly-wheel on the boat.” Fitzgerald’s use of simile helps provide a link between abstract and actual realms, reality and illusion, and love and its inevitable disappointments.
The title, “Winter Dreams,” refers to the powerful desire for status and affluence and, with its suggestion of snowy barrenness, sets the tone for the story that unfolds. Dexter forms his greatest aspirations for his life during a season of death and dormancy, an irony that suggests that those aspirations will not be as life-affirming as Dexter imagines. Seasons in general highlight the unstoppable passage of time in the story. As Dexter gets older but no wiser, each year finds him further from the happiness he seeks. He is in many ways a misfit, his surroundings and ambitions out of synch with his humble origins. Fitzgerald highlights Dexter’s unresolved, outsider status early in the story, when Dexter skis across the frozen, snowed-in golf course, using the space for something other than what it was intended. These solitary, wintry outings signal the loneliness that he will never vanquish. The fact that his dreams are born in a lifeless, stagnant season foreshadows the unhappiness and thwarted desires that await him in adulthood.
In the elite world of the Sherry Island Golf Club, the boat emerges not only as a symbol of luxury but also as a powerful reminder of the emptiness a life of indulgence can lead to. The boat makes a memorable entrance, with Judy at the helm, as Dexter enjoys a solitary moment on the raft anchored in the middle of the lake next to the country club. Lost in a reverie, Dexter is filled with the bliss of arrival, having finally reached the success he had long anticipated. Entertaining only the most auspicious of prospects when he looks to the future, Dexter feels at that moment a satisfaction that he may never again experience as intensely. Abruptly interrupting Dexter’s musings, the whirr of the motor overpowers Dexter’s thoughts about the rosy life ahead. Judy speeds across the lake in the boat, foreshadowing the profound ways that Dexter’s ensuing passion for Judy will impact his future happiness.
For Judy, flying behind the boat on a surfboard, the boat is an escape from reality. Her admirers learn quickly that she is too fast to catch and lives solely for her own pleasure. Dexter obeys when she tells him to drive the boat for her, the first of an ensuing string of commands he will obey. As an object of affluence, it shows how truly divorced from reality Judy is. She tells Dexter that she is running from a man she had been dating who has begun to idealize her. The boat is her way of escaping the ways in which men try to make her fit their own dreams and reflect their idealized visions of the perfect woman. Judy hides in the boat again later, when she grows tired of the man from New York who is rumored to be her fiancé. The boat becomes Judy’s haven from the oppressive affections of men who are captivated by her, an expensive toy that whisks her away from commitment or the need to accept responsibility for her actions.
Golf balls, part of the pristine world of the country club, suggest the harm that an idle life can lead to as well as the stringent requirements one must meet to belong to the upper class. Dexter, with his self-made wealth, tries desperately to blend in with this affluent world. The imagery of the golf balls emerges twice, both times reflecting the upper-class ease that the game itself embodies. First, before the spring thaw in the north country, golfers use black and red balls, which stand out better in the patches of snow that linger on the course. This reference comes early in the story, when Dexter is a young caddy, excluded from Judy Jones and her set because he is a middle-class boy of limited means. When Dexter finally gets a toehold in her world, he sacrifices his individuality for the identical white balls he uses at the club where he once caddied.
During Dexter’s once anticipated but ultimately disappointing golf outing with T. A. Hedrick, golf balls, in the hands of Judy Jones, become an emblem of aggression. Judy’s ball hits Mr. Hedrick in the stomach, and her obliviousness, whether feigned or genuine, serves only to further characterize her as a self-centered brat. Although there is little threat of real physical violence in this genteel, upper-class world, the incident suggests that aggression lurks just beneath the surface. Although Judy embodies the light, almost hedonist spirit that would eventually characterize the age, Fitzgerald reminds us in this episode that beneath the fun and leisure, real harm can be done. Judy’s errant ball foreshadows the more potent emotional damage she imparts in trifling with Dexter’s and her other admirers’ affections.