Time, Progress, and Repetition Theme Analysis

Time in “Winter Dreams” moves according to two competing models: Fitzgerald juxtaposes a linear concept of time with a cyclical one. In the linear narrative, Dexter moves from Minnesota to the East Coast and becomes wealthy—his career progress, which occurs in tandem with his aging, is straightforward. However, Fitzgerald also uses the cyclical nature of time, depicted through the seasons, to tell the story of Dexter’s lack of emotional maturation. From the moment he is introduced as an eager, ambitious teenager, Fitzgerald presents Dexter as someone in a perpetual cycle of hope and melancholy, nurtured by his “fleeting brilliant impressions of the summer at Sherry Island.” This cycle is associated with Dexter’s “winter dreams,” which, like the winter season itself, are recurrent and cannot be captured or sustained. While Dexter’s business career makes a linear progression, his psychological state is cyclical. He regularly returns to the island, both physically and in his imagination, until he “awakens” from his dream at the end of the story and realizes that he can no longer return.

Winter is important to the narrative both structurally and symbolically. The story begins and ends in winter, which suggests that Dexter’s journey from being an ambitious youth in Minnesota to a successful East Coast businessman (who is realizing the emptiness of his life) forms a natural cycle. When the story beings, Dexter describes “the long Minnesota winter” as something that “[shuts] down like the white lid of a box,” leaving everything, particularly the golf course, covered in snow. Though it offends Dexter to see a site of so much activity become so “desolate,” he eagerly skis over the course, which he can usually access only for work. At this moment, he feels a part of the rarefied world that the golf course represents, even though that world only truly exists in summer. Dexter’s winter dreams, just like his relationship to the golf course in winter, seem delusional.  

Indeed, at the end of the story (which occurs during another winter), Dexter must reckon with the fact that even though he has achieved tremendous success, his life will never be the one he imagined. He will always, in some sense, be skiing on the golf course in winter—that is, imagining himself to be a part of something that only exists in his imagination. This revelation that his winter dreams will not be fulfilled comes after he learns, once and for all, that he will never marry Judy. This is fitting, as Judy is associated with summer, which is the season when the members of the glamorous Sherry Island Golf Club flaunt their wealth, and also the season that first inspired Dexter’s winter dreams.

The first time Dexter sees Judy is during the summer, and he notices “a sort of glow…shining through her thin frame,” as well as a “feverish warmth.” Their subsequent romantic encounters occur only during the summer—when the weather cools, so do her passions, and when the warmth inevitably returns, so does she.  When Dexter last sees Judy, he describes her as a “slender enameled doll in cloth of gold.” Years later, while contemplating the news of her decline, Dexter watches the evening sun “[sink] in dull lovely shades of pink and gold.” The pink that he had seen in Judy’s “feverish” cheeks and the “gold color” he had noticed on “her neck’s soft down” have faded just like the day’s sun, which parallels Dexter’s acknowledgement that those summers have truly ended and his winter dreams are dead.

Dexter cries then, not only because his realization marks the end of something warm and beautiful, but also because his awareness that he can never return to those summers—just as one cannot relive a day—means that time must march forward, toward eventual darkness. The sun, like Judy, had faded, leaving only the closed gates and “the gray beauty of steel that withstands all time.” The gates refer to those that enclosed the golf club, but they also evoke images of the gates of cemeteries, as well as those which mark the entry to the after-life. Fitzgerald leaves the reader, then, with the awareness that time must move forward, while dreams are cyclical illusions—just as winter and summer cannot coexist, Dexter’s winter dreams can never be his reality.