“Winter Dreams” (1922) is one of F. Scott Fitzgerald’s “Gatsby cluster stories,” which informed the creation of his renowned novel The Great Gatsby. Like The Great Gatsby, “Winter Dreams” features the themes of love and longing, the futility of the American dream, illusion and disillusionment, and the fleetingness of time.

This study guide references Collected Works of F. Scott Fitzgerald (45 Short Stories and Novels), released in 2013 by ESCBO Publishing.

“Winter Dreams” begins in Minnesota when a teenage boy named Dexter Green quits his job as a caddy at the local golf club. Although Dexter tells one of his clients, Mr. Mortimer Jones, that he has chosen to quit because he is “too old,” the next pages of the story reveal his true motive. He has just observed 11-year-old Judy Jones and her nanny looking for a caddy; Judy was imperious with both her nanny and Dexter himself. When the caddy master arrived, Judy dropped her clubs and walked toward the first tee. As soon as the caddy master directed Dexter to pick up the clubs, Dexter quit, not fully understanding his reasons for doing so but needing an “outlet” for the emotions his encounter with the girl inspired.

Several years later, Dexter turns down the opportunity to enroll in a business course at the state university. Instead, he opts to attend one of the more prestigious colleges on the East Coast. After graduating from college, Dexter buys a partnership in a laundry. His laundry business is a success; eventually he runs five branches and, by age 27, owns the largest string of laundries in his section of the country. He eventually sells his business and moves to New York.

The story flashes back to the time when Dexter was in the process of building his business: When Dexter is 23, a wealthy Black Bear Lake patron provides him with a guest card for the Sherry Island Golf Course. There, he again encounters Judy Jones, now an “arrestingly beautiful” young woman (665). That night, Dexter encounters Judy on the lake beside the golf club’s veranda. Judy asks Dexter to drive her motorboat so that she can ride on the surfboard behind it. Dexter speaks to Judy about how to drive her boat, and Judy invites Dexter to dinner the following night.

After dinner the following evening, Judy speaks about her shock and disappointment that a man she “cared about” is “poor as a church-mouse” (667). To “start right” with Dexter and spare herself the “shock” of later finding he is poor, Judy asks Dexter, “Who are you, anyhow?” (667). When Dexter remarks that his career is a “matter of futures” and that he is “making more money than any man [his] age in the Northwest,” Judy kisses Dexter (667). Dexter realizes he has wanted Judy his whole life.

A week later, Judy and Dexter attend a picnic supper together; afterward, Judy leaves with another man. Dexter realizes that he is one of Judy’s many suitors and becomes dissatisfied. Once Dexter convinces himself that he will never marry Judy, he becomes engaged to another girl, Irene Scheerer, whom he intends to marry three months later.

On a night that Dexter and Irene planned to go out to the university club together, Irene suffers a headache and stays at home in bed. Dexter ventures to the club alone. There he sees Judy again, and the two former lovers reconnect. Judy asks Dexter to take her home; as he does, Judy cries quietly to herself. She tells Dexter that she would like to marry him and asks him to come into her home. Dexter agrees to spend the night with Judy.

After his encounter with Judy, Dexter and Irene’s engagement is called off. However, Dexter and Judy are engaged for only one month before Judy terminates the engagement on the grounds that she does not want to take Dexter away from Irene.

Dexter goes east in February to sell his laundries and settle in New York, but he returns west once America enters World War I. Dexter hands over the management of his laundry business to his partner and attends first officers’ training camp.

Seven years after breaking up with Judy, when Dexter is 32 years old, a man named Devlin from Detroit visits Dexter’s New York office to discuss business matters. Devlin mentions knowing Judy, who is the wife of one of Devlin’s best friends, Lud Simms. Devlin expresses pity for Judy: Lud drinks and cheats with other women while Judy stays home and takes care of the children. Dexter is struck by a mix of outrage and despair when Devlin describes Judy first as “a pretty girl” and then merely “all right” (672). Devlin paints Judy in a dull light compared to what Dexter remembers. Knowing that Judy’s beauty has faded, Dexter finds his dream is “gone” (672).