"Winter Dreams" is a short story by F. Scott Fitzgerald that first appeared in Metropolitan Magazine in December 1922, and was collected in All the ... Show synopsis "Winter Dreams" is a short story by F. Scott Fitzgerald that first appeared in Metropolitan Magazine in December 1922, and was collected in All the Sad Young Men in 1926. It is considered one of Fitzgerald's finest stories and is frequently anthologized. In the Fitzgerald canon, it 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." This story first appeared in the December edition of Metropolitan Magazine in 1922. Dexter Green is a middle-class boy who aspires to be part of the "old money" elite. Dexter mentions that he was born in Keeble, Minnesota. His father owns the second most profitable grocery store in the town. He starts out as a teenage golf caddy at a Golf Club in Black Bear Lake, Minnesota, which has been suggested is really White Bear Lake, where Fitzgerald lived for a relatively short time at the Yacht Club. Dexter meets Judy Jones and works under her father, Mortimer Jones, at the club. He clearly has a crush on her. One day, he is assigned to caddy for her but quits instead; he can't abide acting as one of her servants. After college, Dexter gets involved in a partnership in a laundry business. He returns to the Sherry Island Golf Club and is invited to play golf with the men for whom he once caddied. He encounters Judy Jones again on the golf course, only now she is older and amazingly beautiful. Later in the evening Dexter swims to a raft on the lake, and runs into Judy, who is driving a motor boat. She asks him to take over while she rides on a surfboard attached to the boat. After this encounter, Judy invites Dexter to dinner, where their affair begins. He soon finds that he is one of a dozen men she is stringing along. After about 18 months Dexter becomes engaged to Irene Scheerer, a kind but ordinary looking girl, while Judy is vacationing in Florida. When Judy returns, however, she again captures Dexter's heart and asks him to marry her. Dexter breaks off his engagement with Irene, only to be dropped again by Judy a month later. To deal with his heartbreak, Dexter joins the army to fight in World War I. After the War, seven years later, Dexter has become a businessman in New York City. He had become phenomenally rich and hadn't visited his home in years. On a particular day, a man, Devlin, from Detroit visits Dexter for business. During the meeting, Devlin mentions Judy Simms, formerly Judy Jones, the wife of one his friends and explains how she had become a housewife. Dexter becomes interested and learns from Devlin that Judy had settled and her beauty had faded; her husband is also cruel to her. The news hit Dexter hard as he still had love and hope for Judy. Later Dexter realizes that his dream is gone and that he can never return home now.