Dexter Green is fourteen at the beginning of the story. His father owns the second-best grocery store in town and he works as a caddy at the golf club for pocket money.
The effect of winter on Green’s psyche is intense. He lapses into "profound melancholy." It appears that winter severely affects Green’s mental state: it makes him "tremble," "repeat idiotic sentences" and "command…imaginary audiences." In winter, he hallucinates – initially about golf games, which he plays "over the fairways of his imagination."
Fourteen-year old Dexter Green encounters an eleven-year old spoiled brat who instigates him handing in his notice at the golf club. She is Judy Jones – described as being unattractive in a way particular to ugly ducklings who are soon to grow into beautiful swans. Miss Jones is determined to get what she wants: Green to wait on her as her caddy. She drops her bag and marches off across the course. He quits his job rather than wait on her, a decision that surprises him as much as his employer.
Green’s desires are not to just be close to wealth, but to have it. He makes a success of a laundry business. He joins the golf club as a member at 23 and finally beats Mr. T A Hedrick, his opponent in his many fantasies. In so doing, however, he learns that Hedrick is dull and a poor golfer.
When he sees Judy again, she is playing golf and hits Mr. T. A. Hedrick in the abdomen with a ball. She shows no remorse. She is now beautiful, and he is immediately taken with her.
Green is later disturbed from a reverie at the beach by Judy Jones on her boat. She asks him to drive it so she can surf behind the boat. She loves the speed, and Green is captivated by her.
Judy invites Green to dinner. His background forces him to consider what he wears, as he does not have the security of ancestry to allow him to dress carelessly. Judy tells him that she has discovered that the man she is in love with is actually poor, though he had made the pretense of not being so. She is impressed that Green is wealthy and kisses him passionately.
Green is swept up in her and bends to her every whim. She, however, has a succession of suitors, which Green finds painful. But because he was so devoted to Judy, she began to take him for granted. Keen to change this, Green becomes engaged to another girl, Irene Scheerer. Despite his imminent marriage to Irene, his passion for Judy remains. When Judy says “I wish you’d marry me,” Green is confused. He does not tell Judy about Irene, and resumes his relationship with Judy.
Judy and Green are together for only a month. Even on reflection, it still takes Green a long time to actually regret this decision. His relationship with Irene is over, as is his friendship with her family. He finally understands that he loved Judy but could not have her. Green sells up his businesses and goes to war, in an attempt to escape his feelings.
Seven years later, Green is talking to a business acquaintance when Judy’s name comes up. She is now Judy Simms; unhappily married to a brute who treats her poorly. When he is told also that Judy is no longer beautiful, Green is distraught. The version of Judy, young and beautiful, who he had loved, was no longer real.
Green seems to have a compulsion to act in certain ways around women – Judy Jones in particular – although there is no consistency in his responses. Green refuses to caddy for Judy on their first childhood meeting, but is then compelled to give in to her at every other opportunity. It is clear that he wants to possess Judy, rather than just love her. As with many of Fitzgerald’s protagonists, "he wanted not association with glittering things and glittering people – he wanted the glittering things themselves."
When Green hears the tune from his prom, he is at his happiest. It is before Judy has drawn him in fully, and he remains an optimistic and confident young man, "magnificently attuned to life, and …everything about him was radiating a brightness and glamour he might never know again." These words are ironic as he is never again this assured of himself. As Green drives the boat for Judy, he is as zealous in his feelings as he was the first time they met; illustrated by the simile "his heart turned over like the fly-wheel of the boat." His reactions to Judy do seem somewhat mechanical, in that he seems to react involuntarily to her.
Judy epitomizes the tragic beauty of the age when she expresses her frustration at her loneliness – ‘“I’m more beautiful than anybody else,” she said brokenly, “Why can’t I be happy?”'
Green’s deep regret is that he will never possess Judy: "He loved her, and he would love her until the day he was too old for loving – but he could not have her." This causes him to "taste…deep pain," just as he had experienced "deep happiness."
When Green’s dream is "taken from him," his disappointment is not in learning that Judy is unhappy. Green had cherished his idea of Judy as perfect, beautiful, unattainable. But, as Gatsby learns upon reunion with Daisy that "no amount of fire or freshness can match what a man will store in his ghostly heart," Green is crushed to learn that Judy was no longer the girl he loved. It is similar to his experience golfing with Hedrick, who turned out to be a mediocre opponent after years of dreaming of defeating him. With the knowledge that Judy's beauty had faded, for Green it was as if she had died.