F. Scott Fitzgerald divides “Winter Dreams” into six episodes. In the first, fourteen-year-old Dexter Green, whose father owns the “second best” grocery store in Black Bear Lake, Minnesota, has been earning thirty dollars a month pocket money caddying at the Sherry Island Golf Club. He is responsible and honest, touted by at least one wealthy patron as the “best caddy in the club.” His decision to quit his job comes suddenly—proclaimed, to incredulous protests, to be the result of his having got “too old.” Such public excuse masks the real and private reason: Dexter has just been smitten head-over-heels by the willful, artificial, and radiant eleven-year-old Judy Jones, who, with her nurse, shows up at the club carrying five new golf clubs in a white canvas bag and demanding a caddy. Dexter watches her engage in a sudden and passionate altercation with the nurse, which piques his interest and works to align him with Judy. He not only sympathizes with her but also senses that an equally sudden and violent act on his part (his resignation) can be the only possible response to the “strong emotional shock” of his infatuation.
In the second episode, which takes place nine years later, Dexter has become a successful entrepreneur in the business world. His laundries cater to moneyed patrons by specializing in fine woolen golf stockings and women’s lingerie. Playing golf one afternoon with men for whom he once caddied, Dexter contemplates his humble past by studying the caddies serving his party, but the reverie is broken when a golf ball hits one of the men in his party in the stomach. It was driven by Judy Jones, now an “arrestingly beautiful” woman of twenty, who, with her partner, nonchalantly plays through Dexter’s foursome.
After an early-evening swim, Dexter is resting on the raft farthest from the club and enjoying strains of piano music from across the lake. Judy approaches by motorboat, introducing herself and requesting that Dexter drive the boat so that she can ride behind on a surfboard, making clear that she is dallying to delay returning home, where a young man is waiting for her. The encounter ends with her offhand invitation to Dexter to join her for dinner the following night.
In the third episode, visions of Judy’s past beaux flit through Dexter’s mind as he waits downstairs for Judy, dressed in his most elegant suit. When she does appear, though, Dexter is disappointed that she is not dressed more elaborately. In addition, her depression disturbs him, and when, after dinner, she confides that the cause of it lies in her discovery that a man she cared for had no money, Dexter is able to reveal matter-of-factly that he is perhaps the richest man of his age in the Northwest. Judy responds to this information with excited kisses.
The fourth episode forms the culmination of Judy’s tantalizing and irresistible charm. It shows a dozen men, Dexter among them, circulating around her at any given moment, always entranced, alternately in and out of her favor.
After experiencing three ecstatic days of heady mutual attraction following their first dinner, Dexter is devastated to realize that Judy’s attentions and affections are being turned toward a man from New York, of whom she tires after a month. Thereafter, she alternately encourages and discourages Dexter, and when, eighteen months later, he realizes the futility of thinking that he could ever completely possess Judy, he becomes engaged to a girl named Irene Scheerer, who never appears as an actual character in the story. In contrast to the passion and brilliance that Judy inspires in him, Dexter feels solid and content with the “sturdily popular” and “intensely great” Irene.
One night when Irene has a headache, which precludes her going out with him, Dexter passes the time by watching the dancers at the University Club and is startled by the sound of Judy’s voice behind him. Back from Florida, Hot Springs, and a broken engagement, she seems eager to tantalize Dexter again and asks if he has a car. As they drive around the city, Judy teases him with “Oh, Dexter, have you forgotten last year?” and “I wish you’d marry me.” Dexter is confused about whether the remarks are sincere or artificial, but when, for the first time, she begins to cry in his presence, lamenting that she is beautiful but not happy, Dexter is passionately drawn to her once again, despite his better judgment. When Judy invites him to come inside her house, Dexter accepts.
The fifth episode takes place ten years later. Dexter reminisces about how the passion rekindled from that one night lasted only a month, yet he feels that the deep happiness was worth the deep pain. He knows now that he will never really own Judy, but that he will always love her. At the outbreak of the war, having broken off his engagement with Irene and intending to settle in New York, Dexter instead turns over the management of his laundries to his partner and enlists in an officer’s training program.
The final episode occurs seven years after the war. Dexter is now a very successful businessperson in New York City. Devlin, a business acquaintance from Detroit, makes small talk by remarking that one of his best friends in Detroit, at whose wedding Devlin ushered, was married to a woman from Dexter’s hometown. At the mention of Judy’s name, Dexter pumps Devlin for more information and learns that Judy’s life has become an unfortunate one indeed—her husband drinks and runs around with other women while she stays at home with the children. Worst of all, though, is the fact that she has lost her beauty. When Devlin leaves, Dexter weeps, not so much for the fact that Judy’s physical beauty has faded, but that something spiritual within him has been lost: his illusion, his youth, his winter dream.