What happens in Winter Dreams?

Dexter Green's life story is told in six parts. It begins when he's fourteen, then relates the full story of his long, tumultuous affair with Judy Jones. Dexter first sees Judy at the golf course where he works as a teenager. He falls in love with her, but doesn't pursue a romantic relationship with her until he becomes a successful entrepreneur. When he realizes that there's no hope for them, he gets engaged to Irene. Judy seduces him into one more month of passion, but they break up in the end. Years later, after Dexter has become a successful businessman in New York, he hears that Judy has married and lost her looks. He weeps not so much for her as for his youth and illusions—his "winter dreams." 

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Summary

(Comprehensive Guide to Short Stories, Critical Edition)

F. Scott Fitzgerald divides “Winter Dreams” into six episodes. In the first, fourteen-year-old Dexter Green, whose father owns the “second best” grocery store in Black Bear Lake, Minnesota, has been earning thirty dollars a month pocket money caddying at the Sherry Island Golf Club. He is responsible and honest, touted by at least one wealthy patron as the “best caddy in the club.” His decision to quit his job comes suddenly—proclaimed, to incredulous protests, to be the result of his having got “too old.” Such public excuse masks the real and private reason: Dexter has just been smitten head-over-heels by the willful, artificial, and radiant eleven-year-old Judy Jones, who, with her nurse, shows up at the club carrying five new golf clubs in a white canvas bag and demanding a caddy. Dexter watches her engage in a sudden and passionate altercation with the nurse, which piques his interest and works to align him with Judy. He not only sympathizes with her but also senses that an equally sudden and violent act on his part (his resignation) can be the only possible response to the “strong emotional shock” of his infatuation.

In the second episode, which takes place nine years later, Dexter has become a successful entrepreneur in the business world. His laundries cater to moneyed patrons by specializing in fine woolen golf stockings and women’s lingerie. Playing golf one afternoon with men for whom he once caddied, Dexter contemplates his humble past by studying the caddies serving his party, but the reverie is broken when a golf ball hits one of the men in his party in the stomach. It was driven by Judy Jones, now an “arrestingly beautiful” woman of twenty, who, with her partner, nonchalantly plays through Dexter’s foursome.

After an early-evening swim, Dexter is resting on the raft farthest from the club and enjoying strains of piano music from across the lake. Judy approaches by motorboat, introducing herself and requesting that Dexter drive the boat so that she can ride behind on a surfboard, making clear that she is dallying to delay returning home, where a young man is waiting for her. The encounter ends with her offhand invitation to Dexter to join her for dinner the following night.

In the third episode, visions of Judy’s past beaux flit through Dexter’s mind as he waits downstairs for Judy, dressed in his most elegant suit. When she does appear, though, Dexter is disappointed that she is not dressed more elaborately. In addition, her depression disturbs him, and when, after dinner, she confides that the cause of it lies in her discovery that a man she cared for had no money, Dexter is able to reveal matter-of-factly that he is perhaps the richest man of his age in the Northwest. Judy responds to this information with excited kisses.

The fourth episode forms the culmination of Judy’s tantalizing and irresistible charm. It shows a dozen men, Dexter among them, circulating around her at any given moment, always entranced, alternately in and out of her favor.

After experiencing three ecstatic days of heady mutual attraction following their first dinner, Dexter is devastated to realize that Judy’s attentions and affections are being turned toward a man from New...

(The entire section is 994 words.)