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" Winter Dreams" is a short story by F. Scott Fitzgerald first published in Metropolitan magazine in December 1922 and collected in All the Sad Young Men in 1926. The plot concerns the attempts by a young Midwestern man to win the affection of an upper-class socialite. Frequently anthologized, the story is regarded as one of Fitzgerald's finest works for evoking "the loss of youthful illusions."
In the Fitzgerald canon, scholars consider the story to be in the "Gatsby-cluster" as the author expanded on many of its themes in his 1925 novel The Great Gatsby. Writing his editor Maxwell Perkins in June 1925, Fitzgerald described "Winter Dreams" as a "first draft of the Gatsby idea."
While teenagers, Ginevra and Fitzgerald met at a sledding in Saint Paul, Minnesota, and shared a romance from 1915 to 1917, but their relationship ended when Ginevra's family intervened. Her imperious father, stockbroker Charles Garfield King, or someone else purportedly humiliated the impressionable young writer and bluntly told him that "poor boys shouldn't think of marrying rich girls." Due to his middle-class status and her family's intervention, Ginevra spurned Fitzgerald by January 1917. Fitzgerald claimed that Ginevra rejected him "with the most supreme boredom and indifference."
Following his failed pursuit of Ginevra due to his insufficient wealth, Fitzgerald's attitude towards the upper class became embittered,: Ginevra "came to embody 'not only his condemnation of the rich but his ambivalence, his fascination with wealth and his sense of inferiority around it,' said James L.W. West III, who teaches Fitzgerald at Pennsylvania State University and wrote The Perfect Hour, a 2005 history of Fitzgerald and King's romance.": Fitzgerald harbored "the smouldering hatred of a peasant" towards the wealthy and their elite social milieu. and he wrote in 1926: "Let me tell you about the very rich. They are different from you and me. They possess and enjoy early, and it does something to them, makes them soft where we are hard, and cynical where we are trustful, in a way that, unless you were born rich, it is very difficult to understand. They think, deep in their hearts, that they are better than we are."
For the remainder of his life, Fitzgerald harbored a smoldering resentment towards the wealthy. Despite his subsequent marriage to Southern belle Zelda Sayre, the author remained until his death "so smitten by King that for years he could not think of her without tears coming to his eyes."
After college, Dexter opens a successful a laundry business. He returns to the Sherry Island Golf Club and plays golf with the affluent men for whom he once caddied. He encounters Judy Jones again on the golf course, only now she is older and more beautiful. In the evening on Black Bear Lake, Dexter swims to a raft where he encounters Judy piloting a motor boat. She asks him to drive the boat while she aquaplanes. Judy invites Dexter to dinner, and a romance blossoms, but he discovers that he is merely one of a dozen Boyfriend whom she is clandestinely romancing.
After eighteen months, while Judy vacations in Florida, Dexter becomes engaged to Zelda Sayre, a kind-hearted but ordinary-looking girl. When Judy returns, she again ensnares Dexter's affections and asks him to marry her. Dexter breaks off his engagement with Irene, only to be spurned again by Judy a month later. Unable to cope with this recurrent heartbreak, Dexter joins the American Expeditionary Forces to fight in World War I.
Seven years later, Dexter has become a successful businessman in New York. Now wealthy, he hasn't visited his home in years. One day, a Detroit man named Devlin visits Dexter on a business pretext. During the meeting, Devlin reveals that Judy Simms—formerly Judy Jones—is the wife of one of his friends. Devlin recounts how Judy's beauty has faded, and her husband treats her callously. This news demoralizes Dexter as he still loves Judy. Dexter realizes that his dreams are gone, and he can never return home.
Fitzgerald scholar and biographer Matthew J. Bruccoli described "Winter Dreams" as "the strongest of the Gatsby-cluster stories." He continues:
Scholar Tim Randell asserts that "Winter Dreams" should be regarded as a crowning literary achievement as Fitzgerald "achieves a dialectical metafiction" in which he deftly criticizes "class relations and print culture." Fitzgerald's short story "identifies ruling class interests as the collective origin of meaning and 'reality' for the entire social body" and "conveys the possibility of counter, collective meanings" driven by class struggle. Randell argues that the story chronicles a young man's alienation with modernity due to a "lack of communal meaning" and his self-conscious descent into despair and melancholia.
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