Story Analysis of ‘Winter Dreams’ by F. Scott Fitzgerald


It’s Day 22 of the #A2ZChallenge. This year, I invite you to read and discuss short stories with me. Each day, I bring you a ‘Read of the Day,’ a short story in English, so that we can indulge in the joy of reading. You can visit my site daily for a short story with analysis and participate in the discussion in the comments.

Read of the Day 

Today, we will read Winter Dreams by F. Scott Fitzgerald. You can read the short story online here.

About the Author 

F. Scott Fitzgerald was an Irish American author and screenwriter. Often hailed as the leading voice of a “Lost Generation” of the 1920s and the Jazz Age, Fitzgerald is counted among the greatest authors of the 20th century. He wrote four novels, four collections of short stories, and 164 short stories in his lifetime. Some of his famous works include The Great Gatsby, Tender Is the Night, and This Side Of Paradise. 

Story Analysis 

Winter Dreams by F. Scott Fitzgerald is counted among his greatest short stories. The story is a thematic precursor to his famous novel, The Great Gatsby, as admitted by Fitzgerald, who described Winter Dreams as “a sort of first draft of the Gatsby idea.” 

The story is about Dexter Green, a fourteen-year-old boy who works as a caddy for pocket money until he meets Judy Jones, a wealthy eleven-year-old girl. She looks down upon him for doing menial work, leaving him feeling inferior. The story chronicles Green’s ambitions which he calls his ‘winter dreams,’ and his struggles to attain social prestige, wealth, love, and respect. 

Judy Jones arouses all the materialistic desires in Dexter Green, who yearns to live up to her ideal. He keeps chasing one goal after the other to get closer to her ranks of the powerful elite. She takes notice of him when he tastes success and courts him.

Fitzgerald paints a picturesque story where you can vividly visualize the characters in motion against the scenic backdrops. 

There was a fish jumping and a star shining and the lights around the lake were gleaming.

Dexter realizes the truth about Judy Jones soon enough and gets engaged to Irene Scheerer, who’s wife-material. However, his passion for Judy Jones gets the better of him. 

He sat perfectly quiet, his nerves in wild clamor, afraid that if he moved he would find her irresistibly in his arms. Two tears had rolled down her wet face and trembled on her upper lip.

“I’m more beautiful than anybody else,” she said brokenly, “why can’t I be happy?” Her moist eyes tore at his stability–her mouth turned slowly downward with an exquisite sadness: “I’d

like to marry you if you’ll have me, Dexter. I suppose you think I’m not worth having, but I’ll be so beautiful for you, Dexter.” 

A million phrases of anger, pride, passion, hatred, tenderness fought on his lips. Then a perfect wave of emotion washed over him, carrying off with it a sediment of wisdom, of convention, of doubt, of honor. This was his girl who was speaking, his own, his beautiful, his pride.

Winter Dreams by F. Scott Fitzgerald is a story of lofty ambitions and unbridled passion. Life’s not as simple as it seems as Dexter realizes the bitter truth at the end. He realizes all that he was chasing was an ephemeral dream. 

How did you find Winter Dreams by F. Scott Fitzgerald? 

* I’m participating in the #BlogchatterA2Z Challenge.

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Tina Sequeira
Tina Sequeira is a marketer and moonlighting writer. She is passionate about tech, creativity, and social justice—dabbling in and writing about the same.

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