fitzgerald's use of the dream...

"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 era', as many of its themes were later expanded upon in his famous novel The Great Gatsby in 1925.

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. One day decides he is too old to work there but in reality, he quits his job not because of his age but because he doesn't like feeling inferior to the people for whom he is caddying. 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. We next see Dexter several years later as a single, successful New York business man. He meets a client who recalls having attended Judy Jones' wedding. The client describes Judy's husband's alcoholism and torrid affairs, and says that Judy has "faded."

The reality of Judy's life conflicts with Dexter's vision of her, and her downfall destroys Dexter's "winter dreams." The dream of being with her -- an unfulfilled dream -- has kept him from realizing that the glory of his social climb lay in its progression rather than in its fulfillment.