Literary Analysis Essay Winter Dreams Short

Winter Dreams Summary

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The preeminent literary voice to capture the self-indulgent status seeking spirit of the denizens of the Jazz Age, F. Scott Fitzgerald published the short story Winter Dreams in MetropolitanMagazine in 1922 and included it in his 1926 collection All the Sad Young Men.  In it, Dexter Green is a self-made man attempting to elevate his social position while pursuing his ideal woman.  Similarities to the title character of Fitzgerald’s 1925 novel The Great Gatsby are more than coincidental.  The author wrote Winter Dreams while formulating the early stages of Gatsby.  There is also an autobiographical component to Winter Dreams as Fitzgerald, like Dexter, was raised as a member of the Midwestern middle class and summered at White Bear Lake which was not unlike the exclusive Black Bear Lake of the short story.  Fitzgerald composed numerous other stories in the same period that along with Winter Dreams became the basis for Gatsby and are referred to as the “Gatsby Cluster”.

The story opens with a fourteen-year-old Dexter, the son of one of his town’s grocery store owners working as a caddy at a local golf club.  It is wintertime which has harsh effects on Dexter’s state of mind.  He falls into melancholy moods and he has hallucinations about golf games.  Dexter meets Judy Jones at the golf club.  She conducts herself in a way that makes it clear that she is spoiled.  She is just eleven years old and is described of as being unattractive, but as also possessing a beauty that will eventually emerge with her coming of age.  She is demanding and wants Dexter to serve her as her caddy.  When she storms off leaving her bag on the course for Dexter to retrieve, Dexter quits his job rather than having to wait on her.  He and his boss are equally taken aback by his action, a situation which decades later is echoed in the story A&P in John Updike’s 1962 collection Pigeon Feathers and Other Stories when Sammy the cashier quits his job in the wake of the three bathing suit clad girls who enter the store in defiance of the rules.

By the time Dexter is twenty-three he has a laundry business that is doing well.  He knows by that time that he wants his own wealth, not just to be close to it.  He becomes a member of the golf club and sees his past fantasies of beating T.A. Hedrick become reality although it does not feel impressive to him as Hedrick is not a strong golfer.  Judy reenters Dexter’s life while playing golf at the club and in keeping with the self-centered attitude of her youth, is not the least bit concerned when she hits Hedrick with a ball.  As had been foreshadowed she is indeed now a beautiful woman to whom Dexter is attracted at once.  She asks him to drive her boat so that she can surf behind it. She is enthralled by the speed, which further draws Dexter to her.  She asks him to dinner where he learns that she is disenchanted with the man in her life because he had pretended to be wealthy but is not.  She is moved by Dexter’s wealth and kisses him.  In spite of Judy taking on a series of suitors and neglecting Dexter, he dedicates himself to her in a manner that Fitzgerald later will replicate with Jay Gatsby and Daisy Buchanan.  Dexter becomes engaged to a girl named Irene hoping to rekindle Judy’s interest in him.  He does not know how to respond when Judy suggest that she wishes he would marry her.  He does not tell Judy about Irene, but gets back into a relationship with Judy.

The reconnection lasts only a month at which point Dexter has lost Irene as well as any connection to her family with whom he had been friendly.  He comes to realize that Judy was unobtainable in spite of his love for her.  He sells his business and goes to war to avoid his feelings.  Seven years pass and he learns from an acquaintance that Judy is unhappily married to a man who mistreats her and that her beauty has faded.  Dexter knows that the Judy he was smitten with no longer exists.

In his youth, Dexter was idealistic.  At that point in time it did not matter whether or not he was wealthy.  Life offered endless opportunities.  Getting old means having fewer opportunities and facing loss in life.  Judy loses her beauty while Dexter loses the idealized woman to whom he devoted his life.  At the end of the story Dexter has lost not just Judy but part of himself and can no longer live via his memories of youth and dreams.  Dexter was a romantic who ends up enveloped in sadness.  Gatsby too is a romantic who ends up engulfed by sadness and faces an even more tragic end that did Dexter.

The Dark Side of the American Dream

The “winter dreams” of the story refer to the American Dream that Dexter comes to embody, but success brings a high cost, and social mobility restricts Dexter’s capacity for happiness. Dexter is from humble origins: his mother was an immigrant who constantly struggled with the language of her adopted homeland. The central irony of the story is that realizing the American Dream yields bleak rewards. For example, when Dexter was a young caddy, he dreamed about success and wealth and the happiness they would bring. When he finally beats T. A. Hedrick in a golf tournament, however, the triumph brings him little joy. Dexter is able to transcend middle-class inertia but, despite his tireless efforts to advance his fortunes, forced to accept that money cannot buy happiness.

Dexter has an ambiguous relationship with the bluebloods and idle rich who populate his social world. On one hand, he is proud of his self-made status and has no respect for the men for whom luxury and wealth were a given. Still, the men are emblems of a world to which Dexter wants to belong. In pursuing Judy, he is attempting to validate his claim as a bonafide member of the upper class. Dexter feels that he is a newer, stronger, and more praiseworthy version of the Mortimer Joneses of the world, but he still mimics the rich in gesture and appearance. He pays meticulous attention to his appearance, concerned with small details that only an outsider who was trying to disguise himself as a man of wealth would really notice. Dexter’s position in this world is precarious, and there is no room for error in appearance or etiquette. Through Dexter and the world of earned distinctions that he comes to represent, Fitzgerald exposes the hollowness that comes from the aggressive pursuit of the American Dream. Wealth and social status substitute for strong connections to people, eclipsing the possibility of happiness of emotional fulfillment.

Reality versus Idealism

Reality and fantasy prove to be constantly at odds with each other as Dexter and Judy search for stability and meaning in “Winter Dreams.” Dexter is the victim of his so-called winter dreams, adolescent fantasies that he is never able to fulfill. As he searches for happiness and love, he unwisely focuses his quest exclusively on Judy Jones, making her the sole object of his romantic projections. However, rather than provide fulfillment for Dexter, Judy and her displays of affection simply trigger more yearning. Dexter never sees Judy for who she really is; rather, he sees her as an ideal of womanhood and the embodiment of perfect love. Later, Judy reveals her self-serving nature when she confesses that she is breaking off relations with a man who has pursued her simply because he is not of adequate financial means. Dexter, still blinded by his idealistic view of Judy, cannot digest this information, because it suggests the reality of who Judy is.

Although Dexter recognizes the real threat of harm beneath Judy’s charm and beauty and tries to convince himself that he is no longer in love with her, he cannot fully divorce himself from the romantic, uncontrollable attachment he has to her. Ultimately, Dexter becomes the victim not of Judy’s fickle behavior but of his own stubborn ideals. Time and again, Dexter and Judy struggle with contradictions between reality and fantasy. On their first date, Dexter is disappointed that Judy appears in an average dress and, instead of the pomp and ritual he expected, blandly tells the maid that they are ready to eat. In their ambiguous and protracted courtship, Judy treats him with “interest . . . encouragement . . . malice . . . indifference . . . [and] contempt.” The reality of this relationship is bleak, but the idealistic vision of what it could be enables it to limp along.

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