How does Dexter Green in "Winter Dreams" compare to author F. Scott Fitzgerald?

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Dexter Green, like Fitzgerald himself, hails from a fairly prosperous Midwestern family. But, also like Fitzgerald, he remains tantalizingly outside the charmed circle of the 'old money' elite. In his capacity as a caddy at an upscale country club, Dexter gets to rub shoulders with the upper classes, which adds greatly to his fascination with them. This is a characteristic he shares with his creator. Throughout his work, Fitzgerald shows a fascination bordering on obsession with the opulent lives of America's social elite (The Great Gatsby being the most obvious example).

Yet the nearer Dexter/Fitzgerald gets to the old rich, the more he realizes that there's an unbridgeable gap between them. He may be an acute observer of their strange customs and habits, but that's mainly because he himself isn't really a part of their world. Ultimately, there's an artificiality about the old money elite which repels him but at the same time draws him in, against his better judgment. Dexter's fling with Judy and Fitzgerald's notoriously stormy marriage to Zelda are prime illustrations of this.

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Like Dexter Green, F. Scott Fitzgerald grew up amidst wealthy people, but his family's financial situation was modest by comparison. And like Dexter Green, Fitzgerald aspired to rise in affluence, even if he didn't aspire to join society in a conspicuous, perhaps stuffy manner.

Judy Jones, the woman with whom Dexter is taken, shares many significant traits with Zelda Sayre, the woman with whom Fitzgerald fell in love. Both Judy and Zelda come from wealthy families, and both are fairly spoiled. Another important quality they share is an appetite for thrill-seeking: Judy isn't afraid of being impertinent and likes to ride at top speed in her boat, and Zelda was famous for similar stunts. Both women pushed boundaries and had remarkable self-confidence, suggesting that Fitzgerald found that quality attractive.

As reflected in Dexter Green, and later, in Jay Gatsby, Fitzgerald seemed to understand that it was risky to marry one's personal hopes and aspirations to another human being. Both Judy and Zelda (as well as Daisy, in The Great Gatsby) were, for all their allure, deeply flawed women who in the end, let Dexter and Fitzgerald down because of the superhuman expectations the men placed on them.

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I think one of the principal parallels that we can draw between the protagonist of this excellent short story and the author is the way in which Fitzgerald himself fell in love with his wife, Zelda, who captured the beauty, glamour and wealth of the upper class life that he then went on to lead in the same way that Judy Jones is described as representing wealth and social prestige to Dexter Jones. Note the following quote:

Judy Jones, a slender enameled doll in cloth of gold: gold in a band at her head, gold in two slipper points at her dress's hem. The fragile glow of her face seemed to blossom as she smiled at him.

Note the way that in this quote the gold acts as a symbol of Dexter's dreams and the elusive glamour that Judy represents. The way that Fitzgerald fell in love with his wife represents a similar attraction, where the women that both men fell in love with stand for so much more than just being the objects of affection. Both Dexter and Fitzgerald were involved in World War I, and both likewise pursued the American Dream with tragic results, as Fitzgerald had to cope with the madness of his wife and his own breakdown just as Dexter had to suffer the loss of his dreams and hopes.

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How would one compare Dexter Green in F. Scott Fitzgerald's short story "Winter Dreams" to the author F. Scott Fitzgerald himself?

In the short story "Winter Dreams" by F. Scott Fitzgerald, Dexter Green is a teenage caddy at a golf course in Minnesota at first. Meeting a snobbish rich girl named Judy Jones causes him to quit his job. Years later, after he has achieved success in the laundry business, he meets her again, becomes infatuated, and has an affair with her. At the same time, she is seeing other men. Later, he becomes engaged to a woman named Irene but breaks up with her when he reconnects with Judy Jones. Again, his affair with Judy lasts just a short time. In the end, he hears that Judy has got married and has lost her looks.

Scott Fitzgerald was born in Minnesota in 1896. His father was not very successful at business, but his mother had a substantial inheritance, so Fitzgerald grew up in the upper middle class. He achieved early success and fame as a writer at the age of 24 with the publication of his first novel, This Side of Paradise, in 1920. In the same year, he married Zelda Sayre, who he considered his muse.

Concerning comparisons between F. Scott Fitzgerald and Dexter Green, they were both born in Minnesota, they both achieved success in their careers at an early age, and they both socialized in wealthy circles although they were not born into them. Additionally, while Fitzgerald was studying at Princeton, he had an affair with a wealthy socialite named Ginevra King, and he was infatuated with her just as Dexter Green is infatuated with Judy Jones in "Winter Dreams." Ginevra King became the inspiration for the character of Daisy in The Great Gatsby and most likely also for the character of Judy Jones in "Winter Dreams."

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How would one compare Dexter Green in F. Scott Fitzgerald's short story "Winter Dreams" to the author F. Scott Fitzgerald himself?

While more parallels can be drawn between the character Jay Gatsby in F. Scott Fitzgerald's The Great Gatsby and the character Dexter Green in Fitzgerald's short story "Winter Dreams," some parallels can also be drawn between Dexter and the author Fitzgerald himself.

One similarity is that both men enlisted when World War I started. Dexter enlisted right after both of his romances failed. He had just broken off his engagement to Irene to rekindle his romance with Judy Jones, but that romance only lasted one month. Likewise, Fitzgerald dropped out of college at Princeton University to join the U.S. Army at the outbreak of World War I. However, unlike Dexter, who never married, after enlisting, Fitzgerald met the woman he would marry.

We can also draw similarities between the women both men fell in love with. Fitzgerald's famous wife Zelda Sayre is very much like Judy who Dexter fell in love with though never married. Editor Charles E. May of Comprehensive Guide to Short Stories, Critical Edition describes Dexter, at the age of 14, as falling in love with a "willful, artificial, and radiant eleven-year-old" girl named Judy (eNotes, "Summary"). Being willful, she's particularly inclined towards having her own way and throwing temper tantrums. She grows up to be very beautiful and treats all of the men who court her like play things. Like Judy, Zelda was the daughter of a judge and a Southern aristocrat who was very used to having her own way. She was even inclined towards public displays, such as "turning cartwheels with her friends on the Alabama capitol steps" (Croasdaile, "Zelda Fitzgerald: Love and Madness"). Like Judy, Zelda was also beautiful and had many men court her. Also, like Judy, Zelda at first broke off her engagement to Fitzgerald when it looked like he would not be able to financially support her. But unlike Judy, when Fitzgerald's first book became a success, Zelda quickly married him, whereas Judy never married Dexter.

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