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.