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Winter Dreams Summary

Summary and Analysis of Winter Dreams by F. Scott Fitzgerald

F. Scott Fitzgerald’s short story “Winter Dreams” chronicles the relationship between Dexter and Judy through the years and how it affects Dexter. The story revolves around themes of the American dream, love, happiness, illusion, and reality.

Winter Dreams | Summary

Dexter is the son of the owner of the second-best grocery store in the area, to earn pocket money he works as a caddy at the golf club. One day he meets a girl called Judy, who came to play there, who tries to boss him around and tries to hit her nurse with a golf club. After some time the overseer arrives and he announces his desire to quit, much to the disappointment of the owner who reveals that he is the best caddy he has. We are told that his reason to quit the job is that he suddenly decided he is too old for the job, and the readers are teased about the mysterious winter dreams that dictate his actions.

Dexter after his experience with child Judy is resolved to improve his social standing. After his college life at a state university, he takes a loan and talks his way into the laundry business. He caters mainly to the wealthier customers specializing in the things they need to get cleaned like woolen golf stockings, knickerbockers, etc… And gains the loyalty of the customers. By the age of twenty-seven, he owned the largest laundry string in the part of the country. Back when he was twenty-three, he gets invited to play golf by Mr. Hart, on the same golf course he used to caddy in. There he meets Judy again as her ball strikes one of his companions. Judy appears unapologetic and did not care about what she had done or how it affected others. Dexter’s companions comment on Judy’s beauty. Dexter meets Judy again later that day as she asks him to drive the boat for her as she wanted to surf.

He goes to Judy’s place the next day to meet her and s disappointed that she showed up in casuals, her parents are not at home, after a short conversation she tells him how she is upset about her previous lover and how he did not tell her that he was poor before that day, she tells Dexter how she is interested in him and asks him if he was rich. Only after Dexter replies that he is probably richer than most men of his age does Judy smile and kiss him. He soon realizes how Judy has relations s with several other men and he is just one of the many men she ‘sees’, but he is okay with it. Judy soon leaves Dexter and gets engaged to another man only to break her engagement to move on to fresher men. Dexter now meets Irene and gets to know her family their engagement is approaching.

One day Dexter goes to meet Irene her mother tells him how she has a headache and has to leave without even seeing her once. He meets Judy later that day, while driving her back home she breaks down and asks him why she can’t have happiness even after being so beautiful, only to follow it with a marriage proposal that leads him to break up with Irene. All of his effort and commitment go down the drain as Judy yet again leaves him for another man. He later joins the First World War after he returns from the war he sells his laundry chain and moves to New York.

When he is thirty-two and rich, a colleague of his if he knew Judy who is now married to a man who cheats on her and Judy spends her time at home with her children, the marriage is strained but Judy seems to love him as she forgives him for everything. They then have a discussion on beauty ad age after all of which Dexter feels like getting drunk. He lies down in his office lounge alone weeping over the loss of his winter dress as he realizes he doesn’t care about her anymore.

Winter Dreams | Analysis

The story can be said to mainly revolve around Dexter’s pursuit of wealth and to an extent love as these two factors seem to affect the trajectory of his life the most. Dexter can be seen working from a young age even though there is no need for him to do so, other than to gain more pocket money, where he gets his winter dream that affects everything he does from then, this dream is nothing but the great American dream, a dream of materializing goals and social mobility.
e joins the state college to surround himself with rich people though it does make him feel like an odd one of the bunch. Even after he gets rich his insecurities force him to wear only the best well-tailored clothes so as to not send a wrong message about his class, thinking wearing shabby clothes is a luxury that his children can have but not him, this desire to appear rich also stems from his desire to hide his roots and lineage.

The next major influence in his life was perhaps Judy. Judy is presented as a narcissistic, manipulative uncaring liar throughout the story. The first two times we meet her she shows no remorse or second thought about hurting people, the first time Judy meets Dexter he s an entitled little girl who tries to order him around, she also tries to hit her nurse in the chest with a golf club. If that attitude could be perhaps excused due to her very young age, the second time Dexter meets her is when she hits one of Dexter’s companions with her golf ball and does not even bother to apologize for it. It is her uncaring and bossy attitude that propels Dexter to quit his job as a caddy and go in pursuit of his winter dreams. These two dreams of the protagonist are shown to at least partially coincide with the day he goes to meet Judy at her house. Judy declares her interest in him and asks him if he were rich because she only dates rich people. From here we see several overt references to how Judy becomes co-opted as a part of his winter dream. This is most apparent when he goes for the dance alone since Irene had a bad headache and couldn’t accompany him, and Judy shows up in a golden costume and greets him as he was getting bored. Perhaps it is a subconscious association of wealth and class with Judy that attracts him to her even after he understands her true nature.

Similarly, Judy’s perception of self is linked to her class and gaining the affection of men, it is this craving for affection that makes her create a harem of men around her that she pretends to be interested in while she hops around searching for new sources of validation. A particularly vile example of this would be when Judy jeopardises Dexter’s marriage by confessing her love and proposing to him and leaving him after a month.

Winter Dreams | Title of the Story

The story is named “Winter Dreams” in reference to Dexter’s dream of social mobility when he was but a young boy when during a winter when the business was on a low, he dreams of defeating T.A Hedrick who was the best golfer who played in Sherry Island. This dream coupled with Judy’s bad attitude compels him to quit his job as a caddy and pursue his “Winter Dreams.”


The story is told by a third-person limited narrator. The narrator often breaks from the story to tell the readers certain pointers and observations that help us better understand the situation of the protagonists. The story is also divided into six segments that follow the chaos that Dexter’s life is, due to the constant interference of his crush Judy, this segmentation and brokenness also represent the lives of these two characters. Judy and her self-worth and goals revolve around others and her constant hunt for validation, and Dexter similarly constantly tries to hide himself and his identity to project his new class and does not want to be mistaken for being in the class in which he was a part of before his ventures and success.






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