The short story "Winter Dreams" by F. Scott Fitzgerald is a prelude to his class novel The Great Gatsby. The two share many themes, motifs, and archetypes. This story, told from third-person limited point of view, follows Dexter Green who begins as a young boy living in Minnesota. Dexter excelled at golf and later became a caddy to the wealthy people who would play at the Sherry Island Golf Club.

Around age fourteen he saw a beautiful girl of eleven yelling at her nurse, Hilda. Miss Jones, the daughter of Mortimer Jones, approached Dexter and asked where the golf teacher was. Dexter said he was busy, so the nurse asked if Dexter could help them find a caddy. When Dexter explained that he was the only caddy available and he had to stay until the caddy-master returned, Miss Jones smashed one of her clubs on the ground and then hit her nurse with it. Dexter watched and laughed as the nurse twisted the club away from the girl. Just then the caddy-master returned and asked Dexter to caddy for the girl, but Dexter decided to quit instead, which ends part one of the story.

In part two Dexter attends the university, but he longs for glittering things. After college he began a laundry business. At age twenty-three a man for whom he used to caddy invited Dexter to golf at his old club. As they were playing, they heard someone yell and then a ball hit Mr. T.A. Hedrick, a part of their foursome, right in the stomach. Mr. Hedrick complained that they shouldn't let women on the course. A girl approached looking for her ball. Dexter recognized her as the eleven-year-old girl who had thrown a tantrum almost a decade ago. The men all noticed Judy Jones beauty.

Later that evening Dexter went for a swim in the lake and heard a boat approach. Judy Jones recognized him from earlier that day. She explained that she was escaping a man at her house who was in love with her. She asked Dexter to drive the boat so she could side her surf board behind then she asked him to come over to dinner the following night.

Part three begins the following evening with Dexter arriving at Judy's house. They have dinner and afterwards she begins to cry. She's upset because a man she cared about had revealed to her that he was poor. Dexter admitted that he probably makes more money than most men his age, which led to her kissing him. Dexter realized he had wanted Judy Jones for a long time.

Part four follows their romance, which sometimes included Judy going off with other men. Dexter realized he was one of almost a dozen who periodically dated her. By winter he wanted to marry her, but she would say "maybe someday." By the end of the following summer the son of a rich man was rumored to be engaged to Judy, so their relationship fizzled. Dexter continued to show up at places where he thought he might see Judy; however, within six months he was engaged to Irene Scheere. One night he went to pick up Irene, but she had gone to bed with a headache, so he went to the University Club. Judy Jones spotted him, and they left together. She complimented his eyes and confessed that she wished he would marry her. Then she mentioned Irene's name, and he realized that she knew he was engaged. She began to cry and asked to be taken home. She sobbed about how beautiful she was, and how she really would like to marry him. Then she asked if he would come in with her, and he agreed.

In part five he begins by saying that he did not regret that night even though the relationship with Judy only lasted another month. He did feel bad that he hurt Irene and upset her parents. When the war came to America in March, he went to training camp. When he returned, he went into the laundry business. By the age of twenty-seven, he owned the most laundry facilities in his section of the country, so he sold them and went to New York.

Part six occurs seven years later. Dexter was thirty-two years old and living in New York. A man named Devlin from the midwest came to his office one day and told Dexter about a wedding he had been in. It was for Judy Jones. Dexter had heard that she got married. Then Devlin said that her husband treats her poorly and that her looks were just all right. Dexter was stunned; he almost felt drunk trying to comprehend how Judy Jones had faded. It shattered his dream of her perfection and his desire to have it as his own.