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"Winter Dreams" is a short story by F. Scott Fitzgerald that was first published in Metropolitan magazine in December 1922 and later collected in All the Sad Young Men in 1926. It is now in the public domain world-wide. The plot concerns the attempts by a young man to win the affections of an upper-class woman. The story, frequently anthologized, is regarded as one of Fitzgerald's finest works "for poignantly portraying the loss of youthful illusions."
In the Fitzgerald canon, the story is considered to be in the "Gatsby-cluster" as many of its themes were later expanded upon in his famous novel The Great Gatsby in 1925. Writing his editor Max Perkins in June 1925, Fitzgerald described "Winter Dreams" as "a sort of first draft of the Gatsby idea."
Fitzgerald biographer Matthew J. Bruccoli described "Winter Dreams" as "the strongest of the Gatsby-cluster stories." He continues:
Like the novel, it examines a boy whose ambitions become identified with a selfish rich girl. Indeed, Fitzgerald removed Dexter Green's response to Judy Jones' home from the magazine text and wrote it into the novel as Jay Gatsby's response to Daisy Fay's home.
Scholar Tim Randell has asserted 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 antagonism. 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 melancholy.