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.