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

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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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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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