Luminosity in “Winter Dreams”: the Art and Elegance of Fitzgerald’s Prose

There’s no question that the anthology Fiction 100 does exactly what it sets out to do: highlight carefully curated short stories that represent each aspect of the craft, from short prose to anecdotes. F. Scott Fitzgerald’s work, “Winter Dreams,” fits in perfectly with this collection. A master of the short story, Fitzgerald made his mark in publications like Esquire and The Saturday Evening Post (Bruccoli 1). He regularly returned to themes that dominated his early adult years: success, love, reputation, and material gain, of which “Winter Dreams” is an excellent example. Taking the American “rags to riches” story and turning it on its head, this masterpiece maintains magic throughout with a strong sense of hope and possibility, rich scenes, a universally relatable theme, and strong dialogue – a combination which generates and maintains a special luminosity that has withstood time.

The first thing readers experience with “Winter Dreams” is fairly obvious, but must be said: the title alone hints at its haunting quality. By referencing “dreams,” we instinctively understand that some components may be dramatic, contradictory, fantastic, or unfulfilled. The title represents Dexter’s longing, and while it demonstrates the power of dreaming and the possibilities that may come from a sense of limitless possibility, it also hints at disappointments, because dreams don’t always come true. This sense of possibility infused in the first page of this story continues to carry over. In fact, it radiates off every page and is directly responsible for this story’s reputation as powerful and luminous. The first element is the possibility of financial success. In “Winter Dreams,” Dexter climbs the ladder, cleverly leveraging his education and shrewd business sense to invest in a laundry business, soon “making more money than any man my age in the Northwest” (Fitzgerald 4). Dexter’s innate understanding of the finer things in life helps him, and shows that, despite the fact that his mother “was a Bohemian of the peasant class and she had talked broken English until the end of her days,” he could reach the financial comfort of his peers (4). Fitzgerald then enhances the pervading sense of possibility with a wry recognition of what it takes to “make it.” Fitzgerald intimates that Dexter will succeed early on, not merely for his foresight in quitting his first position as a caddy, but his innate knowledge of his potential and its limitations. Fitzgerald gives us an opportunity to reflect on the cruel reality of those born to a lower station; Dexter knows that “carelessness was for his children” (4). Confidence pushes him forward, and he moves forward seemingly effortlessly. Fitzgerald makes no references to Dexter’s financial struggles, moments of doubt, or pitfalls, and this alone is like a dream.

The sense of possibility that shines through does so because Dexter chooses his future. He is, through his own hard work, merely one generation away from ultimate success (4). Fitzgerald indicates that Dexter, while being of peasant stock, is actually better than the counterparts he seeks to emulate. He is stronger; he is made to work hard, and if he does, he will succeed. This is a relatable characteristic to many readers then and now, and as Fitzgerald noted “He had seen that, in one sense, he was better than those men. He was newer and stronger” (4). Dexter admits that he may be trying to replicate their ways through careful study, but at the same time, his raw materials are actually of superior quality. He may be behind in opportunity in the beginning, but he is ahead in drive and in capability. As the narrator observes, “All about him rich men’s sons were peddling bonds precariously, or investing patrimonies precariously, or plodding through the two dozen volumes of the ‘George Washington Commercial Course’ (1). Dexter, of course, was not: he was making his first of many sensible investments.

Fitzgerald paints a picture that, with success, one can get anything one wants, from respect, to a love object, to a top job. Dexter meets Judy Green because he travels in the same circles; he has the opportunity to court her because he has money. We learn that he has been given this opportunity over Judy’s former beau, a fine but poor man about whom Judy laments “My interest in him wasn’t strong enough to survive the shock” (4). He remembers being a “proud, desirous little boy,” and we remind ourselves that his drive and willingness has already gotten him many things in life.

Environment adds a special quality to Fitzgerald’s work, adding to a sense of heightened drama. Early on, our main character, Dexter, is driven to make the most of himself, and the dead Midwestern winter is like a blank canvas, ready to serve as a backdrop to his hopes and goals. We feel Dexter’s dissatisfaction with his current situation, and we feel him chomping at the bit to change his circumstances and avoid the dreaded winter: “At these times the country gave him a feeling of profound melancholy – it offended him that the links should lie in enforced fallowness, haunted by ragged sparrows for the long season” (Fitzgerald 1). Later, when Dexter received the news that Judy’s beauty has faded, he “lay down on his lounge and looked out the window at the New York skyline into which the sun was sinking in dull lovely shades of pink and gold” (9). At many points in the story, our main character’s actions are set off by a sweeping description of his surroundings, as if the situation were seared into his memory (and ours). These scenes bookend the story, also appearing in the first paragraph: “It was dreary, too, that on the tees where the gay colors in summer fluttered in summer there were now only the desolate sand-boxes knee-deep in crusted ice” (1).

The theme of hope extends beyond our main character’s belief in himself, but his longing for someone he could not have. Judy may have broken off the engagement, but a small part of Dexter remembered the “deep happiness” that he had shared with her. Even happily married, he could still hold onto the illusion that Judy may give him another chance, lost in her beaus, courting, and frippery. While he changed, he expected her to stay, crystallized, and ever just out-of-reach.

Experts claim that not only is Fitzgerald’s work powerful on its own, but it served as the basis for Fitzgerald’s bestselling, iconic novel, The Great Gatsby. The themes and issues addressed in this story were so compelling that the author revisited them repeatedly (not only in Winter Dreams, but in All the Sad Young Men and The Beautiful and The Damned). He couldn’t shake the draw of material wealth, and the possible emptiness that still plagued some of America’s most golden of couples. “Winter Dreams” was the first exploration of this subject. As a Midwesterner, Fitzgerald was intimately acquainted with the deep freeze of winter, and he taps into the unhappy undertones of his protagonist’s life, his unrequited loves, and the general tone of the story. What also makes “Winter Dreams” so luminous, beyond style, is the parallel between Dexter Green and F. Scott Fitzgerald himself. Fitzgerald was a Midwesterner and was all too acquainted with the frigid temperatures that shaped his youth. More importantly, as a Princeton graduate, he was aware of the advantages of the upper class, but struggled to afford even the basics. He met Ginevra King, a socialite, and was inspired by her as a “just out of reach” woman who drove him to make something of himself (Bruccoli). Later, Fitzgerald courted Zelda Sayre, by all accounts charming, beautiful, and wealthy, but was unable to convince her to marry him while he struggled financially. This real-life inspiration added a poignancy and realness to it that sticks in our consciousness. “Winter Dreams” is also luminous because it takes an unusual bend at the end. It is highly memorable because it does not end in a positive manner. Instead, our protagonist fights to later feels like he settled, and then discovers that the woman he held up on a pedestal also settled. It’s haunting, and it’s also highly relatable to the average reader. Even Judy demonstrates that material possessions aren’t everything: she laments, in front of the “great white bulk” of her father’s home, “I’m more beautiful than anybody else. Why can’t I be happy?” (8). She may have everything, possession-wise, but she still feels that she is lacking.

“Winter Dreams” is a timeless, relatable short story. Dexter Green strives to achieve a woman just out of reach, and he knows that she is out of his league. She ends up marrying someone else, and he pines for her while still trying to settle down with a more suitable, albeit unexciting match. How many readers have learned the important, but painful, lessons of compromise, and for how many people will this be one of many experiences?

Works Cited

Bruccoli, Matthew J., editor. “A Brief Life of Fitzgerald.” F. Scott Fitzgerald: A Life in Letters, Scribner, 2010, library.sc.edu/spcoll/fitzgerald/biography.html.

Fitzgerald, F. Scott. “Winter Dreams.” ENG 494, public.wsu.edu/~campbelld/engl494/winterdreams.pdf.

Pickering, James H. Fiction 100: An Anthology of Short Fiction. Pearson, 2016.