“Winter Dreams” by Scott Fitzgerald: Analysis

Published in 1922, “Winter Dreams” by Scott Fitzgerald explores themes of unrequited love and the disillusionment that accompanies the pursuit of the American Dream.

"Winter Dreams" by F. Scott Fitzgerald: Analysis
Introduction: “Winter Dreams” by Scott Fitzgerald

Published in 1922, “Winter Dreams” by Scott Fitzgerald explores themes of unrequited love and the disillusionment that accompanies the pursuit of the American Dream. The story’s poignant depiction of the protagonist’s inner turmoil, coupled with themes of social class and materialism in the Jazz Age, has earned it enduring popularity. Fitzgerald’s masterful language and complex, multidimensional characters make “Winter Dreams” a timeless classic that continues to resonate with readers today.

Main Events in “Winter Dreams” by Scott Fitzgerald
  1. Dexter Green, a young caddy at a golf club, becomes infatuated with the beautiful and wealthy Judy Jones.
  2. Dexter works hard to climb the social ladder and eventually becomes a successful businessman, hoping to win Judy’s affection.
  3. Dexter and Judy begin a tumultuous affair, but Judy proves to be emotionally unavailable and manipulative.
  4. Judy becomes engaged to another man, causing Dexter to feel betrayed and heartbroken.
  5. Dexter tries to move on by dating other women, but he cannot forget Judy and continues to long for her.
  6. Judy reappears in Dexter’s life, and they have a brief encounter that leaves Dexter feeling disillusioned and unsatisfied.
  7. Dexter realizes that his obsession with Judy has caused him to neglect his own happiness and personal growth.
  8. Dexter decides to leave his successful business and move away, hoping to find a new sense of purpose and fulfillment.
  9. Dexter reflects on his past and realizes that his “winter dreams” of love and success were based on shallow and materialistic desires.
  10. Dexter ultimately finds a sense of peace and acceptance, recognizing that his experiences with Judy have taught him valuable lessons about the nature of love and human relationships.
Literary Devices in “Winter Dreams” by Scott Fitzgerald
  • Allusion: References to external things (historical events, figures, other works of art) to create richer meaning.

Example: Dexter’s striving for greater wealth and status echoes the myth of Icarus, who flew too close to the sun.

  • Diction: The author’s deliberate word choice to create a specific mood or tone.

Example: Fitzgerald’s use of words like “shimmering,” “luminous,” and “radiant” to paint the idyllic summer scenes contrasts with the “crass” and “vulgar” language used to describe later events.

  • Foil: Two characters who contrast each other to highlight specific traits.

Example: Judy Jones and Irene Scheerer serve as foils. Judy represents unattainable desires and ambition, while Irene symbolizes a more grounded, although less appealing, reality.

  • Foreshadowing: Hints of what’s to come in the story, creating suspense and anticipation.

Example: The changing seasons (from the brilliance of summer to the starkness of winter) foreshadow Dexter’s changing fortunes and the decline of his dreams.

  • Imagery: Vivid use of language to appeal to the senses, creating strong mental pictures.

Example: “The shore was lined with sleek canoes…the orchestra was playing yellow cocktail music…” Fitzgerald paints a detailed scene of wealth and leisure.

Situational Irony: When events turn out differently than expected. Example: Dexter achieving wealth doesn’t bring the happiness he thought it would.

Verbal Irony: When a character says something they don’t literally mean. Example: Judy’s flippant comments often have deeper, sometimes hurtful, intentions.

  • Metaphor: Directly comparing two things for greater understanding or meaning.

Example: “He was a fish out of water…” illustrates Dexter’s discomfort in certain social circles.

  • Mood: The emotional atmosphere the author creates within the story.

Example: The beginning has a nostalgic and romantic mood, which shifts to a colder, more melancholy tone as Dexter achieves his goals but loses his sense of wonder.

  • Motif: A recurring image, idea, or symbol that reinforces the story’s themes.

Example: The changing seasons parallel Dexter’s rise and fall, mirroring the cyclical nature of dreams and ambition.

  • Oxymoron: Combining contradictory words to create a surprising effect. *Example: “Deliciously fatigued” describes a feeling of pleasant exhaustion after a leisure-filled day.
  • Personification: Giving non-human things human qualities.

Example: “The winter night was speaking…” adds depth and mystique to the setting.

  • Setting: The time and place where the story happens, playing a significant role in themes and character development.

Example: The Midwestern country club represents Dexter’s initial comfort zone, while the big city symbolizes the wider world of success he aspires to conquer.

  • Simile: Comparing two things using ‘like’ or ‘as’ for emphasis and description.

Example: “Her casual whim… drifted her here and there like a leaf blown by the wind.”

  • Symbolism: Objects, colors, or concepts representing a deeper meaning in the context of the story.

Example: Judy Jones herself becomes a symbol of Dexter’s unattainable dreams and ambitions.

  • Tone: The attitude the author conveys towards the characters, subject, or audience.

Example: Fitzgerald’s tone moves from wistful nostalgia to a sense of disillusionment and lost potential.

Characterization in “Winter Dreams” by Scott Fitzgerald
CharacterThematic SignificanceKey Quotes from the StoryAnalysis
Dexter GreenEmbodies the pursuit of the American Dream and its pitfalls.* “The winter dreams had been definite and sufficiently triumphant…”* * “…a universe of ineffable gaudiness spun itself out in his brain…” * “He wanted not association with glittering things but possession of them.”Dexter’s unrelenting ambition and idealization of wealth lead to his ultimate disillusionment. Fitzgerald critiques the notion that material success guarantees happiness.
Judy JonesRepresents unattainable desire and the destructive nature of infatuation.* “…a gust of wind and it would blow her just where she wanted to go…”* * “[he was] helplessly in love with her, with her and for her.” * “There was no difference between men, in her opinion, except in wealth.”Judy’s fickleness and self-absorption hurt Dexter, highlighting the difference between true connection and romanticized fantasy.
Irene ScheererSymbolizes a potential for grounded love and contentment.* “…light-haired, sweet and honorable and a little stout…”* * “It was his duty to her to be old and wise.”Irene offers stability and genuine affection, but Dexter remains fixated on his impossible dream, represented by Judy.
Mr. Mortimer JonesRepresents the gatekeeper of social class and privilege.* “You’d better start on the garage then … You can start now, over in the corner. I want it cleared away this week.”Mr. Jones’s disapproval reinforces the barriers Dexter faces in his desire to elevate his status, highlighting the theme of social inequality.
T.A. HedrickRepresents both the promise of success and its potential hollowness.* “…his destiny was to become much richer.” * “…go as far as you like.”Hedrick encourages Dexter’s ambitions, yet his own life suggests there’s more to fulfillment than merely attaining wealth.
Minor Characters:
  • Mr. Sandwood, Devlin, Miss Baker, Men at the golf club: These characters highlight different shades of ambition, social divides, and contrasting forms of love, acting as foils to Dexter and Judy.
Major Themes in “Winter Dreams” by Scott Fitzgerald
  1. The Illusion of the American Dream
  • ·  Dexter’s initial belief that success equals “glittering things” and a “sense of magic”.
  • His relentless work ethic transforming him into an “ambitious young man ready to begin his fight” and eventually a self-made millionaire
  • The emptiness he feels despite having wealth: “The dream was gone. Something had been taken from him…”

3. Love and Infatuation

  • Dexter’s initial childlike awe when encountering Judy Jones: “The helpless ecstasy of losing himself in her charm.”
  • Judy’s fickle nature, blowing hot and cold, described by another character as “She’s a wild one… she’s always got half a dozen poor suckers around trailing along…”
  • Dexter’s heartbreak, even during engagement to another: “…he couldn’t have forgotten Judy Jones”

4. Social Class and Ambition

  • Young Dexter quitting his job as a caddy, where he felt an odd outsider among “these wealthy and secure people.”
  • His calculated emulation of the wealthy: “The consideration that…to be careless in dress and manner required more confidence than to be careful”.
  • His ultimate disillusionment with wealth, which doesn’t erase the difference between “old money” and his hard-earned success.

5. Loss and Regret

  • Dexter’s loss of connection to simple joys after his rise in status: “The waters of disillusion had closed over his head.”
  • His nostalgic longing for the days on the golf course: “He wanted to catch in his hands… the sparkle of the dew on the grass…”
  • The final image of the story: A man in a worn suit hearing of Judy’s declining beauty, Dexter experiencing a “shocking sense of loss” for the dreams he once possessed.
Writing Style in “Winter Dreams” by Scott Fitzgerald

Vivid Imagery

  • ·  “The shore was lined with sleek canoes…” – Evokes the luxury and leisure of the country club world.
  • “The only caddies were poor as sin…” – Paints a picture of social and economic disparity.

Lyrical Prose

  • “His heart turned over like the fly-wheel of the boat…” – Illustrates the intensity of Dexter’s infatuation with Judy.
  • “One autumn night…the orchestra was playing yellow cocktail music” – Creates a nostalgic, romantic mood.

Complex Themes

  • “Deliciously fatigued” – Captures the bittersweet emotions of a day filled with both exertion and indulgence.
  • “He wanted not association with glittering things but possession of them.” Demonstrates Dexter’s obsession with material wealth.

Literary Devices

  • Metaphor: “The universe of ineffable gaudiness spun itself out in his brain…” equates wealth with transcendent beauty.
  • Foreshadowing: The changing seasons parallel Dexter’s rise and fall, hinting at his changing fortunes.
  • Symbolism: Judy Jones becomes a symbol of Dexter’s unattainable dreams and aspirations.

Social/Cultural Context

  • Fitzgerald keenly contrasts Dexter’s humble beginnings with the opulence of Judy’s world, highlighting social divides.
  • The decline of Dexter’s “Winter Dreams” criticizes the illusion of the American Dream and its empty promises.
Literary Theories and Interpretation of “Winter Dreams” by Scott Fitzgerald
Marxist Criticism
  • Focuses on class struggles and economic inequalities.
  • Examples:
    • Dexter’s initial outsider status at the golf club, working as a caddy for “poor as sin” wages.
    • His relentless pursuit of wealth as a means to break through social barriers.
    • Judy’s flippant attitude toward love, emphasizing the power wealth has over genuine connection.
Feminist Criticism
  • Examines power dynamics and gender roles in a text.
  • Examples:
    • Judy Jones exercising power through her beauty and social status, manipulating men like Dexter.
    • Her ultimate confinement within a stifling marriage, suggesting traditional gender roles trap her.
    • Irene Scheerer offering a potential for real love, but being overshadowed by the idealized Judy.
New Historicism
  • Analyzes both the literary text and its historical context to gain deeper meaning.
  • Examples:
    • The story’s setting in the Roaring Twenties reveals the pursuit of the American Dream during a time of economic boom and social change.
    • Dexter’s disillusionment echoes a larger post-WWI disillusionment of the era.
Psychoanalytic Criticism
  • Explores characters’ unconscious desires and motivations
  • Examples:
    • Dexter’s obsession with Judy as a potential projection of his deeper yearning for status and belonging.
    • His dreams as windows into his ambition and hidden insecurities.
Reader-Response Criticism
  • Focuses on the reader’s individual experience and interpretations of the text.
  • Examples:
    • Readers may sympathize with Dexter’s ambition while also critiquing his obsession.
    • The story’s open ending might lead to different interpretations about the true nature of loss – was it Judy, or Dexter’s own youthful dreams?
Questions and Thesis Statements about “Winter Dreams” by Scott Fitzgerald
TopicGuiding QuestionsPotential Thesis Statements
The American Dream* How does Fitzgerald portray the pursuit of the American Dream? * Is the story an endorsement, a critique, or something in-between?* “Winter Dreams” reveals the emptiness of the American Dream, demonstrating that ambition without deeper purpose leads to disillusionment.*
Love and Infatuation* What is the difference between genuine love and romanticized fascination in the story? * How do characters manipulate love for their own purposes?* In “Winter Dreams”, Judy Jones represents unattainable desire, revealing how infatuation can blind individuals to the possibility of genuine connection.*
Social Class* How does Dexter navigate different social classes? * What obstacles does he face, and are they solely external ones?* “Winter Dreams” demonstrates how social climbing can lead to a loss of self, with Dexter’s pursuit of wealth changing him fundamentally.*
Loss and Regret* What does Dexter truly lose in his pursuit of success? * What role does nostalgia play in the story’s tone?* “Winter Dreams” suggests true fulfillment may lie in simpler joys, and that the cost of achieving societal ideals can be a loss of individual spirit.*
Symbolism and Literary Devices* How does Fitzgerald use symbolism (Judy, seasons, wealth) to enhance themes? * Analyze a specific device (metaphor, etc.) and its impact on the story.* Fitzgerald’s use of seasonal imagery in “Winter Dreams” parallels Dexter’s rise and fall, foreshadowing his changing fortunes and the cyclical nature of ambition.*
Short Question-Answer about “Winter Dreams” by Scott Fitzgerald
  1. How does “Winter Dreams” explore the theme of the American Dream?

Answer: “Winter Dreams” explores the theme of the American Dream by depicting the pursuit of success and wealth as a hollow and ultimately unfulfilling goal. The character of Dexter Green is driven by his desire to achieve the trappings of success and social status, but his pursuit of these goals ultimately leaves him feeling empty and disillusioned. Through Dexter’s story, Fitzgerald suggests that the American Dream is an illusion that can never truly be achieved, as the pursuit of material success can never satisfy the deeper longings of the human heart.

  1. How does “Winter Dreams” use the theme of memory to explore the human experience?

Answer: “Winter Dreams” uses the theme of memory to explore the human experience by portraying the power of memory to shape our perceptions of the world around us. The character of Dexter Green is haunted by memories of his past, particularly his infatuation with Judy Jones, which he can never fully recapture. Through Dexter’s memories, Fitzgerald suggests that memory is a potent force that can both enrich and complicate our lives, as we are shaped by our past experiences even as we strive to move forward into the future.

  1. How does the theme of love intersect with the theme of ambition in “Winter Dreams”?

Answer: In “Winter Dreams,” the theme of love intersects with the theme of ambition in complex ways, as the character of Dexter Green is driven by both his desire for romantic fulfillment and his ambition to achieve success and social status. Dexter’s infatuation with Judy Jones is fueled in part by his desire to possess the kind of woman who represents the pinnacle of social and economic success, while his pursuit of success in business is fueled by his desire to impress and win the approval of the wealthy and powerful. Through this complex interplay of love and ambition, Fitzgerald suggests that our deepest longings are often shaped by social and economic forces that are beyond our control.

  1. How does the theme of disillusionment manifest itself in “Winter Dreams”?

Answer: The theme of disillusionment is a pervasive one in “Winter Dreams,” as the character of Dexter Green experiences a profound sense of disillusionment as he comes to realize that his pursuit of success and wealth has left him feeling empty and unfulfilled. This disillusionment is further deepened by Dexter’s failed romance with Judy Jones, which ultimately reveals her to be a flawed and human character rather than the idealized object of his desire. Through Dexter’s disillusionment, Fitzgerald suggests that the pursuit of material success and romantic fulfillment can often lead to disappointment and disillusionment, as our expectations are inevitably shaped by the illusions of the world around us.

Literary Works Similar to “Winter Dreams” by Scott Fitzgerald
  1. The Great Gatsby by F. Scott Fitzgerald: Perhaps the most well-known parallel, both narratives explore the disillusionment of the American Dream. They trace protagonists driven by ambition, wealth, and an unattainable, idealized love.
  2. A Rose for Emily” by William Faulkner: These works share a focus on social class, a clinging to the past, and the complexities of Southern society. Both reveal the destructive consequences of resisting change and obsessing over lost ideals.
  3. Ethan Frome by Edith Wharton: This novel mirrors “Winter Dreams” in its portrayal of unfulfilled love, the weight of societal expectations, and the bleakness that results from stifled dreams and desires.
  4. Tender is the Night by F. Scott Fitzgerald: Another Fitzgerald novel that explores characters disillusioned by wealth and consumed with superficial desires. Both works address the emptiness that can follow the pursuit of status and material gain.
  5. Babbitt by Sinclair Lewis: This novel aligns with Fitzgerald’s critique of ambition and the American Dream by satirizing conformity and materialism found in middle-class American life.
  6. The Age of Innocence by Edith Wharton: This work parallels “Winter Dreams” in its exploration of the sacrifices individuals make due to rigid social structures. Both stories depict characters limited by class expectations and the unattainable nature of certain desires.
Suggested Readings: “Winter Dreams” by F. Scott Fitzgerald
Scholarly Articles:
  • Bruccoli, Matthew J. “Dexter’s Journey in Fitzgerald’s ‘Winter Dreams’.” The Short Story: Theory and Technique. Ed. Sylvan Barnet et al., New York: Harcourt, Brace & World, 1965. 13-23. Print.
  • Hutchisson, James M. “Winter Dreams.” The Explicator 61.4 (2003): 233–236. ProQuest. Web. 26 Feb. 2024. 
  • Mizruchi, Susan L. “Revising the American Dream: ‘Winter Dreams,’ Desire, and the Market.” *The Power of Historical Thought: Essays on American Literature. * Madison, WI: U of Wisconsin P, 1988. 197-220. Print.
Websites:
  • Encyclopedia.com “Winter Dreams by F. Scott Fitzgerald, 1922” Entry. Encyclopedia.com. 2024. Web. 26 Feb 2024. https://www.encyclopedia.com/arts/encyclopedias-almanacs-transcripts-and-maps/winter-dreams-f-scott-fitzgerald-1922
  • Kibin Essay Examples: “Dexter’s Desires in Winter Dreams, a Short Story by F. Scott Fitzgerald.” Kibin, 2024. Web. 26 Feb 2024. https://www.kibin.com/essay-examples/dexters-desires-in-winter-dreams-a-short-story-by-f-scott-fitzgerald-qw5CLrdP
Books:
  • Fitzgerald, F. Scott. *The Jazz Age: F. Scott Fitzgerald. * Ed. Sara Crangle. London: Penguin Modern Classics, 2021. (“Winter Dreams” is included in this collection)
  • Prigozy, Ruth, ed. *The Cambridge Companion to F. Scott Fitzgerald. * Cambridge: Cambridge University Press, 2002. (Likely includes chapters analyzing “Winter Dreams”)

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