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Analysis of F. Scott Fitzgerald’s Winter Dreams

By NASRULLAH MAMBROL on April 27, 2022

Winter Dreams presents situations and themes that would preoccupy F. Scott Fitzgerald’s famous novel The Great Gatsby , which also embodies American aspirations for social legitimacy and existential self-worth in the form of a longing to possess a desirable woman. Much like that work’s, its account of the enduring, unrequited yearning of Dexter Green for Judy Jones is a biography of desire itself. Fitzgerald’s artful rendering of the particularities of plot and character serve to make emotionally vivid the trajectory of all too many desires. It passes from the initial perception of an object seemingly imbued with the plenitude and vitality of summer, which promises to replace all that seems lacking in one’s personal winter of discontent; through fits of disappointment and disillusionment to abandonment of the object of desire; and to a final pervading sense of nostalgic loss for the enchanting vitality, however painful, that had once accompanied that yearning— a sense of loss that marks the return of a now-permanent emotional and psychological winter that, like the season itself, is “shut down like the white lid of a box” (108).

analysis essay on winter dreams

It is important to recognize that while Dexter responds to Judy’s beautiful flesh and to the magnetic vitality that “shin[es] through her thin frame in a sort of glow” (110), the ultimate source of her attraction and power is what she unconsciously represents to him: the even greater magnetism of social mastery and its concomitant indifference, an utter self-absorption that assumes the homage of others is completely deserved and to be expected. He sets out single-mindedly to advance himself toward his social goals without realizing that his desire to progress beyond his unexceptional circumstances is driven by hope of acquiring what will capture and hold Judy’s attention. Having money to buy the “glittering things” will buy him social prestige: “Often he reached out for the best without knowing why he wanted it—and sometimes he ran up against the mysterious denials and prohibitions in which life indulges” (112). Judy will become the epitome of those denials, just as she epitomizes the obscure object of desire.

Years later, playing golf with men for whom he once had caddied—and feeling alternately “a trespasser” and superior to them—Dexter encounters Judy for a second time when one of his companions is struck by her “bright” ball. Judy’s mere semblance of apology and defensive challenge (“I yelled ‘Fore’ ”) displays how her casual indifference puts forth a tacit claim to her superior rights. The “careless” tone of her remark, “I’d have gone on the green except that I hit something,” is indeterminately “ingenuous or malicious” (114). The unprincipled carelessness of the moneyed leisure class, so in contrast to Dexter’s painstaking middle-class, entrepreneurial diligence, becomes a motif in Fitzgerald’s account, finally being transformed into Dexter’s inability to care. In the interval, Dexter adopts the careless mannerisms of those long accustomed to wealth, knowing “that to be careless in dress and manner required more confidence than to be careful.” But he also appreciates that authentic “carelessness was for his children” (118).

Judy’s temperament is as “fluctuating and feverish” as her complexion (114), which produces “a continual impression of flux, of intense life, of passionate vitality” that is “balanced only partially by the sad luxury of her eyes” (115). Unfortunately for Dexter, he has an eye, and a soul, for melancholy. This is registered in his fixation on the way her smile “twists her lips down at the corners” (109). Judy’s smile is “preposterous” (110) in its flirtatious insincerity, and the fact that it is at the same time “radiant—blatantly artificial—convincing” is what gives it its “general ungodliness” (109–110). Fitzgerald’s psychological acuity enables him to demonstrate that Dexter’s fixation necessarily entails ambivalence. Judy’s petulant moodiness causes him as much “uneasiness” as the promiscuity of her smile: “Whatever she smiled at— at him, at a chicken liver, at nothing—it disturbed him that her smile could have no root in mirth, or even in amusement” (119).

The most evocative passages in “Winter Dreams” reflect Fitzgerald’s own sensitivity to mood and his gift for conjuring dreaming rapture. One evening, as Dexter listens to a distant piano play “the songs of last summer” while “the moon held a finger to her lips,” he undergoes “a mood of intense appreciation, a sense that, for once, he was magnificently attuned to life and that everything about him was radiating a brightness and a glamour he might never know again” (115– 116). It is at this moment that Judy Jones appears and both disrupts the glamorous placidity (with her motorboat) and remakes it in her own image: fish jumps, star shines, lake lights gleam—“and, for the second time, her casual whim gave a new direction to his life” (117).

One of the first things Judy says to Dexter constitutes a warning he chooses to ignore: that she is in her speedboat in order to escape a man who insists that she is his “ideal” (117). Dexter briefly seduces himself into believing that Judy’s “exquisite excitability” can be “controlled and owned.” But a week later she is seeing other men, though he is gratified that she “take[s] the trouble to lie to him” (121). Her ease in getting the attention of any man and her equal ease in becoming bored with that attention cause Dexter increasing “restlessness and dissatisfaction” after the initial “exhilaration” of being the momentary object of her fickle changeability. Judy strings along all her suitors by alternating neglectful indifference and flirtatiousness, “mak[ing] these forays upon the helpless and defeated without malice, indeed half unconscious that there was anything mischievous in what she did” (121).

Despite knowing that Judy is “the most . . . unprincipled personality with which he had ever come in contact,” despite recognizing that her sole objective is “the gratification of her desires,” despite sensing that the “helpless ecstasy of losing himself in her was opiate rather than tonic,” Dexter feels “no desire to change her” (120–121). He continues to feel as he had years before on the golf course, that “her deficiencies were knit up with a passionate energy that transcended and justified them” (120). His understanding deepens as he also begins to recognize that all the beckoning encouragements and contemptuous slights and indignities to which Judy had subjected him—the “utter indifference she manifested and sincerely felt toward him” (123)—had been due to her need to maintain the integrity of her being against the onslaught of too many would-be lovers. She has unconsciously opted “to nourish herself wholly from within” (121) as a means of protecting herself from the many amorous dalliances that would have left her “soiled long since had there been anything to soil her—except herself” (126). However admirable as a motive, this strategy enables Judy to dominate and humiliate Dexter, along with all the others, and he begins to suspect that she “had played his interest in her against his interest in his work—for fun” (123).

In bitter retreat from an “ecstatic happiness and intolerable agony of spirit,” Dexter tries to accept that he will never possess Judy by concentrating on the “untold inconvenience” she has caused him and on the “glaring deficiencies” she presents as a prospective wife. He also accommodates his loss by becoming engaged to “sweet and honorable, and a little stout” Irene, whose bourgeois stolidity is explicitly contrasted with the glittering Judy and her “incorrigible lips” (123). But, missing Judy’s “poignant, unforgivable, yet forgiven turbulence” (124), Dexter abandons his fiancé at the first sign of her renewed interest. Judy is as enchanting and provocative as ever, and her return to him is the return of “all mysterious happenings, all fresh and quickening hopes” (126). Aware of his engagement, she asks him to marry her, displaying the enormity of her confidence that he could not love anyone else, except as “a childish indiscretion . . . something to be brushed aside lightly” (127). She induces the willing Dexter to believe that she is miserable: “Her moist eyes tore at his stability,” causing “a sediment of wisdom, of convention, of doubt, of honor” to be swept away along with his injured pride (128). Predictably, Judy’s “flare for him” lasts no more than a month. But he feels no regrets—not even for the pain and embarrassment he has caused Irene and her family. Fitzgerald perhaps projects on to his character something of his own exquisite aestheticism and subjects it to his own self-contempt, when he remarks, with parenthetical irony, “There was nothing sufficiently pictorial about Irene’s gift to stamp itself on his mind” (129). Dexter is left with two strong feelings—that he has passed “beyond any revulsion or any amusement” and that even though he can never have Judy, “he would love her until the day he was too old for loving” (129).

Years later, after he has sold his business and moved to New York, these feelings are revived when Judy enters his life for the last time. He learns from a business associate that Judy has married a man younger than she, who “treats her like the devil,” but though he “runs around,” she does not and always “forgives him,” presumably out of love. This news does not seem to upset Dexter. He seems shocked and angered, rather, by the man’s offhand description of Judy as “all right” looking, together with his observation that “lots of women fade just like that” (131–132). On hearing of Judy’s lost allure, Dexter knows “that he had just lost something more, as surely as if he had married Judy Jones and seen her fade away before his eyes” (132). What he has lost to the degradations of time is his winter dream that there are things so exquisite that they can transform and enrich mundane reality. An enchanting vitality and a magnetic melancholy “had existed and they existed no longer” (132). This illusion dispelled, his emotional life is frozen forever. “He wanted to care, and he could not care . . . there was no beauty but the gray beauty of steel that withstands all time” (133). This phrase gathers additional implication retrospectively in view of Dexter’s intimation years before while contemplating the “startling stolidity” of the looming houses of the rich: “The steel of the girders, the breadth and beam and pomp of it were there only . . . to accentuate” Judy’s “slightness—as if to show what a breeze could be generated by a butterfly’s wings” (128).

Fitzgerald couches his account of Dexter and his winter dream of Judy within his developing understanding of how the American class system structures the individual’s emotions and sense of self. Lamenting the recent disappointing disclosure of her present lover’s poverty, Judy pointedly asks Dexter, “Who are you, anyhow?” Dexter replies, “I’m nobody. . . . My career is largely a matter of futures” (119). Initially, Judy’s many suitors make her all the more desirable because of what they signify to him. He compares himself favorably to them within the terms of an established American class discourse about the selfmade man, who, being “newer” than those with inherited wealth, is therefore “stronger.” Yet their polish and savoir faire are to be desired: “In acknowledging to himself that he wished his children to be like them he was admitting that he was but the rough, strong stuff from which they eternally sprang” (118). Dexter’s amorous desires and his social aspirations cannot easily be distinguished. Virtually one and the same, they dictate his determination to become a regional laundry magnate by perceiving the needs of his clients with the same diligent industriousness with which he had once pursued lost golf balls. That said, Dexter’s infatuation with the glittering Judy should not be mistaken for an infatuation with her world, which she transcends: “No disillusions as to the world in which she had grown up could cure his illusions as to her desirability” (123).

BIBLIOGRAPHY Fahey, William A. F. Scott Fitzgerald and the American Dream. New York: Crowell, 1973. Fitzgerald, F. Scott. The St. Paul Stories of F. Scott Fitzgerald. Edited by Patricia Hampl and Dave Page. St. Paul, Minn.: Borealis Books, 2004.

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“Winter Dreams”, analysis of the story by Fitzgerald

Plot summary.

Winter dreams are considered to be one of Fitzgerald’s most accomplished short stories. Published in 1922, Winter Dreams is a play on the American Dreams ideal perpetuated in that era and is a study of class, aspirations and relationships and obsessions through infatuation.

Dexter Green is the character around which the story is based. Son of a grocer in Minnesota, Dexter caddies at the local golf course during the Summer months to earn pocket money. Dexter looks up to the golfers that he caddies for with an aspiration of achieving their status and is inspired to better himself. By chance whilst working he meets the leading female character of the story, Judy Jones, who requests that Dexter caddies for him while she plays golf. Dexter is unable to comply due to other caddying commitments, at which point Judy sends out a potential warning signal that Dexter overlooks by striking her nurse who is with her on the golf course in a fit of frustration and anger, a reaction to her request not being fulfilled. Dexter promptly quits his job as a caddy in frustration.

Dexter demonstrates his determination to succeed by this act and it is the first sign of his desire to achieve his ‘Winter Dreams’. Stretching his finances to attend a highly reputable university, Dexter completes his education, borrows money and establishes himself as the wealthy owner of a chain of laundry businesses in the Midwest. Having achieved a very comfortable level of success he moves to New York to progress his social climb.

Dexter and Judy’s paths cross again on the golf course where once again Judy demonstrates a public display of impetuousness and bad manners to other players. But again Dexter overlooks this as he is becoming obsessed with making her his own, taming her perhaps, and establishing himself as a social equal.

After an evening of water skiing together Dexter and Judy agree to dinner at Judy’s where she admits, after asking Dexter’s permission to cry, that a man that she had been dating was not all he seemed and did not have the financial resources to look after her in the manner that she was expecting. Upon being asked Dexter volunteers that he may well be the wealthiest man in the region. Dexter becomes smitten fully but at this stage Judy disappears with another man, frustrating Dexter even further.

Judy has a number of acquaintances with other men and Dexter makes it his mission to attend an event where she may be present, in his ongoing and blinded attempt to woo her and win her affections. Eventually realizing that his quest is in vain Dexter meets Irene and they agree to become engaged. On the evening of the announcement, Irene is unwell and the engagement is postponed, at which point Dexter bumps into Judy yet again by accident. Judy takes this opportunity to discusses their previous passion together and suggests that he should ask her to marry him.

Taking Judy home that evening and having gone inside with her, Dexter falls hopelessly in love with her. It does not occur to him that he has upset Irene and her family by his actions, nor that his professional standing has been tarnished. All that Dexter can see is the love that he has for Judy, not seeing that her perceived love for him back was waning rapidly.

Events occur that force Dexter back to the East with the intention of selling his business. World War 1 breaks out and Dexter launches himself into basic training as something of a distraction from recent events. When he returns aged 32 Dexter learns that Judy has married a man who turned out to be a heavy drinker who cheated on her regularly. He also learns that she has lost her good looks and stays at home daily looking after her children.

Dexter is hit hard by this information he learns from a friend. He is devastated by the loss of her beauty and her personal situation but more importantly, he rues the time that he wasted pursuing his ‘Winter Dream’.

Winter Dreams – Analysis

Winter dreams studies a number of social issues that were prevalent at the time and are still relevant. Dexter Green was born and raised in a modest family environment and from an early age wanted to better himself financially and socially. His time caddying at the golf club gave him two clear insights into life and social status. He wanted to achieve that level of social mobility but simultaneously showed little patience with his perceived superiors and was keen to progress at almost any cost.

This almost blind determination to achieve his goals included having the appropriate wife and in the early stages of their meetings and liaisons Dexter was blind to Judy’s self-serving shortcomings as well as her impatience, arrogance and lack of respect for anyone. Happy to overlook these distasteful traits he blindly pursued her as almost a personal challenge.

Judy was clearly a spoiled and impetuous lady with no patience or acceptance of anything that didn’t go the way she wanted. Her treatment of staff and companions was disgraceful and she relied on her social standing and good looks to maintain what tenuous relationships she had with men. Working through a number of partners she never became satisfied and adopted an ongoing and relentless pursuit for the ideal partner, little realizing that she did not know how he would manifest himself if she ever did meet him. Settling for less than best due to the passage of time, her reputation and her diminishing looks she may well have regretted opportunities.

Winter Dreams is an insightful view of relationships, aspirations, class divides and social climbing. But perhaps, more importantly, it analyses the sometimes blind obsession that comes from infatuation. Had Dexter taken a more holistic view of events and allowed himself to really analyzed who and what he wanted then his Winter Dream may have had a chance to mature.

The book resonates with many people for many reasons, and there are people that will have perhaps been in similar circumstances to Dexter. Likewise, there may be people reading this from Judy’s point of view who realize that sometimes the best opportunities are staring you in the face yet are not instantly seen. Life lessons – certainly. Entertaining, without a doubt. Deep? Yes if you read between the lines.

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“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

Table of Contents

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

  • Dexter Green, a young caddy at a golf club, becomes infatuated with the beautiful and wealthy Judy Jones.
  • Dexter works hard to climb the social ladder and eventually becomes a successful businessman, hoping to win Judy’s affection.
  • Dexter and Judy begin a tumultuous affair, but Judy proves to be emotionally unavailable and manipulative.
  • Judy becomes engaged to another man, causing Dexter to feel betrayed and heartbroken.
  • Dexter tries to move on by dating other women, but he cannot forget Judy and continues to long for her.
  • Judy reappears in Dexter’s life, and they have a brief encounter that leaves Dexter feeling disillusioned and unsatisfied.
  • Dexter realizes that his obsession with Judy has caused him to neglect his own happiness and personal growth.
  • Dexter decides to leave his successful business and move away, hoping to find a new sense of purpose and fulfillment.
  • Dexter reflects on his past and realizes that his “winter dreams” of love and success were based on shallow and materialistic desires.
  • 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

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

  • 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.
  • 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.
  • 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.
  • 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
  • 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.
  • 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

Short question-answer about “winter dreams” by scott fitzgerald.

  • 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.

  • 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.

  • 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.

  • 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

  • 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.
  • “ 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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
  • 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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analysis essay on winter dreams

Jotted Lines

A Collection Of Essays

Winter Dreams by F. Scott Fitzgerald: Analysis

Fitzgerald wrote his short story “Winter Dreams” while he was drafting The Great Gatsby, which became one of the most celebrated novels of all time. The two works share several thematic and stylistic elements as they each center on a young man from a modest background who strives to be a part of the exclusive world inhabited by the woman he loves. A close comparison of the two works will reveal that while The Great Gatsby becomes a more complex and penetrating critique of the pursuit of the wealth and status, the short story stands on its own as a compelling portrait of a man who is forced to face the illusory nature of his “winter dreams.” 

There are strong similarities between Jay Gatsby and Dexter Green. Although Dexter, unlike Gatsby, came from a middle-class background, (his father owned the “second-best” grocery-store in his town), he subscribes to the same American dream as does Gatsby, who grew up in poverty. Both spent their childhood in the Midwest, and from an early age, were determined to gain entry into the glittering and glamorous world of the rich. Through a combination of ambition and hard work, they achieve their goal and become successful businessmen who are accepted into this exclusive world. 

The process by which they rise to the top, however, is quite different. Fitzgerald clearly outlines the steps Dexter takes to become successful: he attends a prestigious Eastern university and upon graduation learns everything he can about the laundry business. The knowledge he gains, coupled with his confidence and a small financial investment, guarantees his prosperity. Fitzgerald is not as straightforward about Gatsby’s rise. There are suggestions that he may have been involved in a cheating scandal and a bootlegging operation with some shady New York entrepreneurs. Fitzgerald’s inclusion of the possibility that Gatsby may have prospered by his involvement in illegal activities highlights the sense of corruption he finds at the heart of American materialism, a theme he develops more completely in his searing portrait of Tom Buchanan, Daisy’s fabulously rich and morally corrupt husband. 

While both of Fitzgerald’s protagonists start out wanting only the status and power that wealth will afford, they shift their focus to a beautiful woman who embodies their dream and with whom they fall in love. Eventually, each finds little satisfaction in purely materialistic gain. Initially Dexter, like Gatsby, is not a snob; he does not want “association with glittering things and glittering people,” but he does want “the glittering things themselves.” Both men amass fortunes, but their wealth ultimately does not fulfill their dream, which focuses on gaining the love of a beautiful woman who expresses the glamour and promise of that exclusive world. At Gatsby’s extravagant parties, for example, the host retreats to the study, waiting for Daisy to appear, refusing to participate in the hedonistic atmosphere of the gathering. Likewise, Dexter has no social aspirations and “rather despised the dancing men who were always on tap for the Thursday or Saturday parties and who filled in at dinners with the younger married set.” Neither man is affected by the attitudes of others in his pursuit of his dreams, nor does either bear any malice toward the women who repeatedly scorn them. 

Daisy and Judy also are quite similar in character. Each is a shallow, ultimately cold-hearted woman who is entertained, as Fitzgerald describes Judy, “only by the gratification of her desires and by the direct exercise of her own charm.” Like Judy, Daisy enjoys “the mystery that wealth imprisons and preserves, of the freshness of many clothes .. . gleaming like silver, safe and proud above the hot struggles of the poor.” The two male characters have their hearts broken by these lovely women who exhibit “a continual impression of flux, of intense life.” Daisy and Judy are “careless people” who “smashed up things and creatures and then retreated back into their money or their vast carelessness .. . and let other people clean up the mess they had made.” 

Daisy appears to be the crueler of the two, as she allows Gatsby to take the full responsibility for her accidentally running down Myrtle, Tom’s mistress, which results in Gatsby’s murder by Myrtle’s husband. Judy’s only crime is breaking hearts. Readers feel a bit sorry for her when she wonders to Dexter, in a broken voice,”I’m more beautiful than anybody else…. Why can’t I be happy?” But ultimately, Fitzgerald creates a fuller, more sympathetic character in Daisy. 

Through his manipulation of the narrative’s chronology, readers are privy to a demonstration of the intense love Daisy had at one point for Gatsby, revealed when she breaks down in the shower, immediately before her marriage to Tom. Jordan notes how Daisy had to be forced into her wedding dress by her parents, who were determined that their daughter marry so well. Readers also see how she suffers in her relationship with her brutish husband. Fitzgerald portrays Daisy as someone who had the potential for happiness, but was not strong enough to achieve that goal. By the end of the novel, she retreats with Tom into the only world she knows. 

Fitzgerald does not develop Judy into a complete character. Readers never know how she became so callous and shallow, and as a result, they have little sympathy for her, even when they discover at the end of the story that her beauty has faded. Like Daisy, Judy has become a passive wife to an abusive husband, but because readers do not see how that process occurred, as they do with Daisy, her character remains undeveloped and not as interesting as her counterpart. 

The settings of the two works reveal Fitzgerald’s rhetorical brilliance in his poetic descriptions of the landscape. He paints detailed portraits of the landscape that artfully reflect each work’s themes. Throughout much of The Great Gatsby, Fitzgerald concentrates on images that illustrate the corruption at the heart of the American dream. His landscapes become the wastelands of garbage heaps and burned out valleys of ashes. The eyes of Dr. T. J. Eckelberg, a symbol of crass materialism and loss of spirituality, peer down from billboards along the highway. At the end of the novel, however, Fitzgerald presents perhaps the most lyrical passage in literature when he describes Daisy’s green light, representing to Gatsby the possibility of an “orgastic future” with Daisy. 

Fitzgerald’s descriptions in “Winter Dreams” are equally lyrical and resonant. They also reflect the dual nature of the main character’s experience. At the beginning of the story, when Dexter can only fantasize about a golden future, the landscape reflects his depression: the long winter “shut down like the white lid of a box” as he skis over the golf course’s snow-covered fairways. The narrator notes Dexter’s identification with his surroundings when he describes his melancholic response to the links’ “enforced fallowness, haunted by ragged sparrows for the long season” and “desolate sand-boxes knee-deep in crusted ice.” At that period of his life “the wind blew cold as misery” and the sun cast a “hard dimensionless glare.” 

At the beginning of his relationship with Judy, however, when the world is filled with excitement and promise, the landscape dramatically changes. One afternoon, soon after he has run into Judy on the golf course, the sun sets “with a riotous swirl of gold and varying blues and scarlets” and the water turns “silver molasses under the harvest-moon.” 

While Fitzgerald ends the two works with each main character losing the woman he loves, he leads the two in different directions, and as a result, creates two distinct and compelling commentaries on the pursuit of the American dream. As each story draws to a close, Fitzgerald delineates important differences between Dexter and Gatsby. 

At the end of “Winter Dreams,” Dexter accepts the fact that he has lost Judy, and accepts also “the deep pain that is reserved only for the strong” since he had also, “tasted for a little while the deep happiness.” He does, however, receive a shock at the end that alters his vision of the golden world he experienced for a time. When a business associate tells him that Judy has lost her beauty and her vitality, his dream shatters and he breaks down, overcome by a profound sense of loss. Joseph Flibbert, in his critique of the story in the Reference Guide to Short Fiction, argues “As long as he could maintain a vision of Judy as the embodiment of genteel youth and beauty, he could continue to believe in an attainable ideal of power, freedom, and beauty.” The world now becomes cold and gray with no point to the accumulation of material objects. 

Struggling desperately to regain that vision, Dexter tries to picture “the waters lapping on Sherry Island and the moonlit veranda, and gingham on the golf-links and the dry sun and the gold color of her neck’s soft down,” but cannot, insisting, “these things were no longer in the world! They had existed and they existed no longer.” He finally understands that he can never follow the same vision that had compelled him to travel in one direction all of his life. All he is left with now is a sense of emptiness, for “even the grief he could have borne was left behind in the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.” 

Gatsby, however, dies with his vision of Daisy and the promise of a life with her intact. He never sees Daisy’s beauty fade, nor does he realize that she has returned to the safety of her relationship with Tom. His inability to give up his dream earns Nick’s respect and his conclusion that Gatsby was “worth the whole damn bunch put together.” Gatsby becomes a mythic figure in the novel, the tireless pursuer of the American dream—the “fresh green breast of the New World.” Fitzgerald’s closing lines reinforce this mythic dimension when Nick notes Gatsby’s inability to see through the illusion and so remain devoted to his vision of Daisy. Nick echoes this enduring sense of hope in the novel’s last lines as he insists that although happiness eludes people, “tomorrow we will run faster, stretch out our arms farther…. So we beat on, boats against the current, bourne back ceaselessly into the past.” 

Fitzgerald’s exquisite crafting of these two works has created enduring portraits of characters whose fate expresses a deep resonance of the American experience. Through Dexter Green, Fitzgerald has chronicled the journey of a realist, who forces himself to shatter the illusions he has held for so long. In his creation of Gatsby, Fitzgerald presents the romantic, who refuses to give up his pursuit of the woman he loves, who represents to him, all that is possible in America. 

Source Credits:

Carol Ullmann (Editor) Short Stories for Students: Presenting Analysis, Context & Criticism on Commonly Studied Short Stories, Volume 15, F. Scott Fitzgerald, Published by Gale, 2002.

Wendy Perkins, Critical Essay on “Winter Dreams,” in Short Stories for Students, The Gale Group, 2002.

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  • Winter Dreams by F. Scott Fitzgerald: Themes
  • Winter Dreams by F. Scott Fitzgerald: Setting
  • This Side of Paradise: Literary Elements

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  • Winter Dreams

Read our detailed study guide on the short story Winter Dreams by F. Scott Fitzgerald. Our study guide covers Winter Dreams summary , themes, characters, and literary analysis.

Winter Dreams Summary

The story opens in winter, and the main character of the story, Dexter Green skis across the golf course where he cartons in spring and summer to earn some money. His father is the owner of the second-best grocery store in Black-Bear, Minnesota. In April, the spring begins, and the first course of golfers begins. However, unlike miserable spring, the autumn and winter endow Dexter and ignite his imagination. Dexter also imagines that he beats the most esteemed members of the golf club.

During work, Dexter encounters Judy Jones. She is attended by her nurse and asks Dexter to carry her sports. Dexter cannot leave his place because of his duty. Judy shows her tantrums and attempts to hit her nurse with her clubs. When the master of the caddy returns, Dexter gets free to be the caddy of Judy. He quits. The winter dreams dictated him to quit the job of a caddie hastily. These dreams drive him to achieve material success.

In order to take admission in a more esteemed eastern university, Dexter skips the state school. He desires for luxury; however, his desires are declined. Dexter, being confident and articulate, borrows $1,000 off the power of his degree after college. He buys a partnership in a laundry. In the Upper East, he owns the largest chain of laundries by the age of twenty-seven. He sells his business and moves to New York.

The previous description was of the time when Dexter was at the peak of his success. When Dexter is twenty-three years old, he goes back to Sherry Island where once Mr. Hark gave him a ticket to pass a weekend. There were also other competitors, and Dexter feels superior to them and considers himself as not a part of this world. While the four are searching for the ball at the fifteen green, Miss Jones struck Mr. Hedrick in the stomach. Miss Jones wishes to play through yet does not realize that she has struck someone.

She continuously hits the ball while the men praise and criticize her beauty and an alternate behavior. In the evening, Dexter swims in the club’s lake, then stretches out on the springboard and listens to the piano playing at a distance. He feels delighted with the tune. However, the roar of the motorboat of Judy disturbs the peaceful scene. She has left a date because the man believes her his ideal. She asks Dexter to drive the boat to go water-ski.

The next evening, Dexter is waiting for Judy to arrive. He imagines all the privileged men who once loved her. Despite his humble background, he has gained sophistication and polish. Judy is dressed in simple clothes. She tells the maid to serve the dinner and informs Dexter that her parents will not attend them. Dexter feels relief.

After dinner, Judy asks Dexter if she can cry. Judy tells her that a man she was dating tells her that she is poor. When she inquires Dexter about his financial status, Dexter says that he is the richest young man in the region. Both of them kiss, and Dexter feels more passionate about her. 

Dexter shows persistence in his pursuit; however, in a picnic, she leaves him alone and goes with another man. She claims that there is nothing happening between her and the other man, yet Dexter does not believe her. 

Judy plays with different men who try to seek her affection. When summer ends, Dexter takes dwelling at a club in town. He also shows at dance parties when Judy attends. He still feels passionate about her and wants to take her to New York. However, he ultimately urges himself to accept the reality that he cannot take her in a way he wants. He starts working very hard and engages himself to Irene.

Irene and Dexter plan to announce their engagement. However, one night when the engagement is to be announced, Irene faces a severe headache that makes her cancel the plan. Dexter goes back to University Club. There Judy returns from her travels and approaches him. Judy and Dexter go for a drive. 

She flirts with him and asks to marry her. They also talk about their former passion. Judy then asks to be taken home. She cries quietly and repeats her wish to marry him. She offers him to get in. However, Dexter refuses.

Judy’s affection and passion for him cools down after a month. He does not regret that and also that Irene was deeply hurt by his unfaithfulness even though his reputation in the city has been negotiated. He loves Judy more than anything. He leaves for the East to sell him business and settle in New York. However, he is called back to the west because of the outbreak of war. He transfers his business to a partner. He starts basic training and welcomes the distraction of combat.

Seven years later, in New York, Dexter has achieved much success at the age of thirty-two. Dexter is informed that Judy married a friend of Dexter’s business associate. Her husband cheats on her and drinks heavily. Judy is all the time at home with her children. Moreover, Devlin, a business associate, tells him that she has lost her glamor and charm. 

Dexter personally feels the loss of her spark and beauty as his illusion of Judy is eventually shattered. He cries and mourns the past, along with the loss of youth that he will never reclaim.

Background of the Story

“Winter Dreams” is a short story published in December 1922 in Metropolitan magazine by F. Scott Fitzgerald. The story is considered as one of the finest works of Fitzgerald. It deals with the heartbreakingly portraying the loss of the illusions of youth.

Many of the themes of the novel are based on the famous novel The Great Gatsby , published in 1925. That is why the story is regarded as “Gatsby-cluster.”

Historical Context

In the short story Dexter Green, the main character of the short, briefly mentions that that war is coming to America in March. The World War was started in 1914 and ended in 1918. The United States entered the war in the spring of 1917. This period of the war was discerning with economic prosperity because of increased consumption and efficient manufacturing. Moreover, there was possible illegal manufacturing of alcohol or “bootlegging.”

In 1920, the Eighteenth Amendment was passed, which banned the manufacture, sale, and transportation of alcohol. In the same year, the Nineteenth Amendment was also passed, which granted women the right to vote.

Literary Context

Fitzgerald’s novel The Great Gatsby is an account of Jay Gatsby , who is an ambitious man but has a poor and rural background. He wants social prestige, just like Dexter in “Winter Dreams.” Another short story, “The Rich Boy,” was published in 1926 also deals with the destructive effects of illusions.

In all of these works, Fitzgerald deals with the theme of nostalgia and addresses the apparent impossibility of true love. These accounts also deal with the frightening aspects of the American Dream as the rich and socially prominent people encounter unhappy and tragic fates.

Fitzgerald met Ginevra King in 1914. She was a beautiful and appealing girl from Chicago. Fitzgerald was very attracted to her. He was one of many boyfriends. She married someone else. Ginerva is considered to be not only inspiration for the character of Judy Jones in “Winter Dreams;” she is also for Daisy Buchanan in The Great Gatsby .

Characters Analysis

Dexter green.

Dexter Green is the protagonist of the short story “Winter Dreams.” When the story begins, he is a teenager who is very much class-conscious. He lives in Black Bear, Minnesota. The story is an account of his maturation into a successful businessman in New York. Even though Dexter grows professionally and achieves great success, he is not able to grow emotionally until when at the end of the story, he realizes that his youth is gone.

Dexter belongs to a middle-class family and is the son of the owner of a grocery store. He spends his summer working as a caddie at Sherry Island Golf Club. Looking at the wealthy member of the community, Dexter learns to model himself. Even though he belongs to a simple and modest family, he is very passionate about attaining material success and social prestige. 

He does not only want to be equal to the elite members of the golf community. He also wants to be equal to the Eastern elites who have an old and well-established background.

Because of his desire to climb to social order, he skips the state school to attend the university in the East. He then became the owner of the largest chain of laundries in the Middle East. He sells his business and settles in New York.

In this journey of success, Dexter continuously lusts for Judy Jones and falls in love with her. Judy is the daughter of a wealthy man. She is very beautiful. Dexter and Judy have on and off relationships. After his breakup with Judy, Dexter engages with Irene. However, his obsessive love, Judy, makes him break his engagement. Dexter loves Judy less than the status she can offer him, along with her beauty and wealth. 

At the end of the story, when Dexter learns that the beauty of Judy fades away, his “winter dream” also fades away. He was in the constant illusion that proximity and money could offer happiness and security.

Judy Jones is one of the central characters of the story. She is an attractive, charming, and beautiful daughter of one of the wealthy members of the club, Mortimer Jones. She is the obsessive love interest of Dexter Green throughout the story. When she first appears in the story, she is a “beautifully ugly” eleven years old girl who orders Dexter to carry her sports. She transforms into an “arrestingly beautiful” twenty years old lady.

Judy serially dates with a different wealthy man and has a reputation for promiscuity. When Dexter attains success, she starts dating him, along with other men. Dexter proses her to marry her, and she agrees. However, as always, Judy breaks the marriage and marries Lud Simms.

Judy has a carefree and direct personality. She is self-possessed; that is why Dexter feels irresistible. After marrying Simms, she becomes a housewife and has children. She lost her beauty and looks and is in a miserable condition because of her husband’s faithfulness and alcoholism.  

T. A. Hedrick

Hedrick is one of the wealthy members of the Sherry Island Golf Club. One of the winter dreams of Dexter is setback Hedrick in a game. According to Dexter, Hedrick has a reputation of a good player of gold; however, when he plays a game with him, he changes his mind. After attaining excessive wealth, Dexter considers himself superior to other members. He starts a thing of Hedrick as a “bore.”

When all the men search for a lost golf ball, Jody struck Hedrick in the stomach. The presence of Judy annoys Hedrick because she is the only woman in the golf club, and secondly, she has a reputation for promiscuity.

Mortimer Jones

He is the father of Judy and the wealthy member of the Sherry Island Golf Club. Because of the exceptional abilities of Dexter as a caddie, he takes great interest in him when he is fourteen years old. When Dexter decides to leave the job, Jones is very upset; however, he does not know the cause of this decision is his daughter.

Dexter idealizes Jones and wants to be a man of his caliber. He even fantasizes about being as rich as Jones, who emerges from the Pierce-Arrow automobile.

He is Dexter’s business associate and visits him in New York. Devlin is the best friend of Judy’s husband, Lud Simms, and also knows Judy. Devlin casually mentions Judy when he visits Dexter. He tells him that she has lost her beauty and charm. 

He also tells her that she is living in an unhappy marriage as Simms heavily drinks and cheats on her. To Devlin, Judy’s beauty is not at all remarkable and considers her as inferior to Simms.

Irene Scheerer

After breaking up with Judy, Dexter engages with Irene. She is described as a sweet and honorable and light hair woman. When Dexter proposes to marry her, she gives up all of her suitors. She, along with her family, is happy with the engagement. However, the engagement ends when Dexter sleeps with Judy. 

Even though Irene is a beautiful and honorable lady, she is not exciting at all. Dexter does not feel any passion for her that he feels for Judy even though she offers domestic satisfaction and security. 

She is Judy’s nurse. She brings Judy to the golf club when she is eleven years old. She tries to take help from Dexter to teach Judy how to play golf even though he has already been assigned to another member. Judy does not appear to be pleased when Hilda tells Dexter that she cannot play. Hilda’s absence of discretion and her speech reveals that she belongs to the lower class. Judy also tries to hit Hilda on her breast when they walk away from Dexter.

Mrs. Scheerer

She is the mother of Irene. She is very kind and likes Dexter. She is deeply hurt when Dexter betrays her daughter.

He is a successful businessman and admires the passion and work ethic of Dexter. He also offers a weekend guest pass to Dexter to the Sherry Island Golf Club.

Mr. Sandwood

He is a member of the golf club. He plays a golf game with Dexter when he is twenty years old. He is also attracted to the beauty of Judy Jones.

Themes in Winter Dreams by F. Scott Fitzgerald

The american dream: a nightmare.

The title of the story refers to the winter dreams that Dexter embodies. These “winter dreams” are also known as the American Dream. Even though Dexter attains great success and becomes a successful businessman, he pays a great price for it. The social mobility that Dexter attains as a result of wealth, it heavily restricts his capacity for happiness.

Dexter comes from a humble background. His father was the owner of a grocery store, and his mother was an immigrant who consistently struggles with the language. The story revolves around the central irony that the realization of the American Dream produces unwelcoming rewards. 

For instance, when Dexter is a teenager and works as a caddy, he dreams of attaining success and happiness that money will bring. He dreams of defeating Hedrick in a golf match. However, when he finally defeats him, he does not feel much happiness.

Dexter has crossed the middle-class inertia. However, he cannot buy happiness with the money that he tirelessly earns.

Dexter appears to have an unclear relationship with the rich people and the blueblood that reside in his social world. He feels proud of himself and his self-made status and does not respect those who are both with the silver spoon in their mouth. However, Dexter wants to be a part of the world to which these men belong. His pursuit of Judy is not only because he loves her but also wants to attain the social status that comes with her.

Even though Dexter attains great success, and he feels himself to be a novel, more praiseworthy, and stringer version of the world of Mortimer Jones, he still imitates the appearance and gestures of the rich. Dexter pays lots of attention to his appearance. He is so concerned with small details that only an outsider who is disguised as a wealthy man can notice. 

The status and position of Dextress in this world is at risk. He does not have any room for error in etiquette and appearance. Fitzgerald tries to expose the hollowness and emptiness that comes when a person tries to pursue the American Dream aggressively. Through Dexter and the world that he represents, Fitzgerald shows that choosing wealth and social status as a substitute for strong connections to people eclipse the possibility of emotional fulfillment and happiness.

Reality versus Idealism

In the short story “Winter Dreams,” reality and idealism are in constant odds with each other. Judy and Dexter constantly try to search for meaning and happiness in the short story. Dexter becomes the victim of the winter dreams. These dreams are the teenage illusion that he never achieves. In his constant search for happiness and love, he only focuses on Judy Jones. He makes her the only subject for his romantic projections. 

However, instead of providing love and a sense of fulfillment to Dexter, Judy’s display of time-being affection initiates more desire and passion in Dexter. Dexter is unable to see the real Judy and who she is in actuality, rather he takes her as an ideal woman who embodies perfect love.

Judy later reveals her true nature when she tells Dexter that she breaks off with a man who wants to pursue her because of her beauty and does not belong to a strong financial background. Even then, Dexter is blind to see her real nature and his idealistic view of her. He cannot digest the reality as it will make him forgo his idealistic view about Judy, even though Dexter acknowledges the real threat that Judy’s charm and beauty carry. 

He also tries to convince himself that he doesn’t love her anymore. However, he cannot completely separate himself from the uncountable and romantic attachment he has with Judy. Eventually, because of his own stubborn ideals, he becomes the victim of Judy’s inconsistent behavior.

Judy and Dexter, time and again, struggle with inconsistencies between fantasy and reality. For instance, Dexter is disappointed to see Judy in a simple and average dressing. He was expecting ritual and pomp, Judy blandly ordered the maid to serve the dinner. 

Judy treats Dexter with interest, malice, encouragement, contempt, and indifference in their protracted and ambiguous relationship. However, the reality of Dexter and Judy’s relationship is not welcoming at all. However, they both are limp along due to the idealistic vision.

Gender and Ambition

When Judy Jones is introduced in the short story, she is an eleven-year-old daughter of a wealthy Mortimer Jones. She has a perceptible spark and passionate quality that appears to be bewitching to Dexter. However, when she shows imperviousness on the golf course, Dexter decides to quit his job of caddying. 

Moreover, he remembers his winter dreams and resolution that he should not take the order of anyone who is so young. Dexter meets Judy again after several years when he makes his fortune at the laundry business. Now, Judy appears to be “arrestingly beautiful” to him.

One of the interesting things is, the readers do not know anything about the physical appearance of Dexter. The only thing mentioned about him in the story is his background, class, and ambition. However, Judy is described only on the basis of his appearance and how she uses them to lure wealthy men.

The way Fitzgerald characterizes Dexter and Judy mirrors the limitation of gender. Dexter utilizes his energy and passion for creating a business for him, while Judy hopes to find herself a husband through her looks.

Hedrick appears to be scornful of Judy’s propensity to hunt for any wealthy man in the town. He uses a metaphor “big cow-eyes on every calf” for Jody, and it perfectly defines her deliberate actions. She shows fake passion and affection to men and attracts them to marry her, even though she is not sincere with any of them as she has many suitors and thus many options. Just like Dexter, Judy is also planning for her future deliberately. However, Dexter is praised while Judy is criticized.

Both Dexter and Judy consume people like material. The way Judy is indifferent to her suitors and treats them with indifference, Dexter is indifferent to Irene. He believes that apart from a bushel of content, Irene will not bring him happiness. He always looks for happiness in Judy. 

He refuses the domestic comfort offered by Irene for the passion he has for Judy. They both pick people up and then discard them at their own whim. Fitzgerald pointed out the shared hard-minded attitude of Judy and Dexter, and this attitude is born from their ambition for influence and wealth.

Time, Progress, and Repetition

In the short story “Winter Dreams,” time has two competing models. In the story, Fitzgerald has juxtaposed the linear concept of time with the cyclic one. The linear narrative of time deals with Dexter moving to the East and becoming a wealthy man; his career develops and so does his age. The movement of time is linear. While cyclic nature of time is shown through the season, and it shows the lack of emotional maturation of Dexter.

When he is introduced in the story, he is an ambitious and eager teenager. He is presented as someone who is in a perpetual cycle of melancholy and hope, which is nourished by Dexter’s “ fleeting brilliant impressions of the summer at Sherry Island .” The cycle of hope and melancholy is linked with the winter dreams of Dexter, which like the winter season, recurrent and cannot be sustained and captured. 

Though the business and professional career of Dexter is making a linear progression, his physiological progression is cyclic. He returns to the Island both physically and in imaginations until, at the end of the story, he awakens from his winter dream. And then realizes that he cannot return.

Both structurally and symbolically, winter is important to the narrative. When the story begins, it is winter, and when it ends, it is again winters. This suggests the whole journey of Dexter from ambitious youth to a successful businessman is in the form of a natural cycle,

At the beginning of the story, the winters in Minnesota are described as something like a white lid of the box that leaves everything covered in snow. This site of snow, though, offends Dexter as the site of so much activity turns desolate, he passionately skies over the course. At this time, golf represents a part of the rarefied world, and he feels a part of it. 

However, the world only exists in summer. Just like his relationship to the golf course, the winter dreams of Dexter also appear to be delusional.

Certainly, at the end of the story, Dexter realizes the fact that despite the fact he has achieved tremendous success, he can never achieve the life he dreamed of or imagined. He always finds himself imagining skiing on the golf course. He imagines himself to be a part of something that only exists in his dreams/imagination.

When he learns that he will never be able to marry Judy, he also realizes that his winter dreams are never going to be fulfilled. In the story, Judy is associated with summer as it is the season when the wealthy members of golfclub flaunt their wealth and also inspire the winter dreams of Dexter.

The loss of Judy makes Dexter cry not only because he has lost something warm and beautiful but also because he will never be able to get back to that summer, which was a source of reliving for him. His realization means that time must move forward towards the darkness. Like Judy, the sun has faded and only leaves the closed gates. Fitzgerald makes the readers realize that time moves forward while dreams are recurrent and cyclic illusions. The dreams of Dexter can become his reality, just like summer and winter cannot co-exist.

Literary Analysis

“Winter Dream” by Fitzgerald is structured and narrated in a way that mirrors Fitzgerald’s critical view of the world that he has tried to depict in his story. Just like the divided nature in the story, the characters of Fitzgerald are shown as incomplete and fractured as they hunt for wealth and pleasure.

The short story has six sections that vary in length, suggesting the many betrayals and affection of Judy and Dexter’s relationship. Moreover, the particular structure of the story also suggests that there is no coherent core to ground the characters for meaning and stability in their search for identity and self-awareness. 

Certainly, Dexter lacks a clear and definite sense of self. Dexter is the product of fragmentary experiences as the story relates to the aspects of coming-of-age. He struggles to find direction and clarity in Judy that his own life lacks.

The way Fitzgerald narrates the story, his views about the whirlwind lives of Judy and Dexter is very much apparent. Fitzgerald, at several points, directly addresses readers, which makes the story immediate and highlights the fact that he is not only just narrating the story but also extracting some particular details from the lives of his character for some good reasons. The direct addresses are sometimes in the form of rhetorical questions.

The story moves about in time and is an account of the lives of Judy Jones and Dexter Green in just two decades. This narrative and structural choice lend richness and complexity to the description of the gradual draining away of the illusion of Dexter. 

Fitzgerald also proposes the intricate role that is played by different events that shape the response of Dexter to Judy through juxtaposing different disembodied episodes in the personal and professional life of Dexter and therefore set up the high cost of his winter dreams.

Dexter is unable to bury his past. He is always living in his past. For instance, the wound of Judy’s arrogance on the golf course is an impending presence that Fitzgerald invokes to make the disillusionment of Dexter at the end of the story.

Dexter tries to escape from the temporary changes, and the passage of the seasons function as the background to the romantic possession. When the story begins, Dexter is fourteen years old and ultimately offers a quick summary of his rise and progression in life. However, when the story concludes, Dexter is only thirty-three years old. 

The character of Dexter is shown as an ironic juxtaposition in just a few paragraphs. From being a caddy to having his own caddies that run his club for him, Dexter’s life has progressed. The fluid sense of time off, as shown by Fitzgerald in the story, functions to highlight Dexter’s loss of youth and the gap that will increase with time and never get close. 

Fitzgerald’s story “Winter Dreams” is an account of the coming of age of two young people. However, the story also deals with a historical period that serves as a background of on and of the relationship between Judy and Dexter.  The time period, as shown in the story, is the early decades of the twentieth century – from the mid of the first decade to the early 1920s.

The early twenties were known as the Jazz and is more precisely known for the time of unchecked hedonism. Self-gratification was the most popular notion of the time. It was the era of opulent parties, grand social gestures, and fashion trends for the affluent people. It was the time when people were the least concerned about their past and even did not have any regard for the future. 

The time also saw many people endorsing a reckless embrace of the moment as America has emerged as a victorious country from World War I, and entered into extraordinary economic prosperity. Fitzgerald captured the spirit of the age in his image and emerged as the laureate of the Jazz Age. He also embodies freewheeling and hedonistic zeal in his personal life.

In the short story “Winter Dreams,” Fitzgerald tries to avoid the images of the stereotypical images of the time, such as gangsters, speakeasies, and flappers. However, he only deals with certain types of characters. 

The character of Judy embodies all types of girls who are selfish, fickle, and histrionic rich girls. She controls her body and throws over men so as to navigate her way through the social world through her charm and beauty. Judy is so much involved in the moment and does not have much regard for the larger implications of her changes of heart.

On the other side, Dexter is a convert who represents the middle-class imposter standing outside the bars and seduced by the self-indulgence and wealth represented by the dancing couple. To Fitzgerald, those who are not able to escape the world, the pursuit of pleasures alienates them. The unofficial motto of the jazz babies, the flappers, and the idle rich people was “pleasure for pleasure’s sake.” In the character of Judy and Dexter, Fitzgerald tries to indicate the decadence of the Jazz Age.

The recurrent images, structures, and literary devices in a literary text are called Motifs. The emphasis on the idea helps develop the major themes of a work. The following are the motifs in the short story “Winter Dreams” by F. Scott Fitzgerald.

Throughout “Winter Dreams,” Fitzgerald uses the similes to make abstract notions appear concrete, more particularly at the beginning of the story’ for instance, drive to succeed and frustration of love. The similes also propose a harbor that separates reality from illusion.

For example, the first sentences describe some of the caddies, unlike Dexter, as “poor as sin.” Moreover, in winters in Minnesota, the golf course is covered with snow “like the white lid of a box,” and the winds are “cold as misery.” Fitzgerald employed these similes to set the unhappy tone for the story, which he is going to narrate. These similes are preoccupied with the depressing notion of poverty and misery.

With the help of similes, the abstract idea of Dexter’s winter dreams is clarified. His dream of success consists of undeveloped hopes for wealth and success, along with the happiness and satisfaction accompanying wealth. Even though Dexter translates his happiness into reality by becoming the richest man of his region, he is still dodged by the abstract notion, for instance, he is never able to find true love and accepts the responsibility of being in relationship with someone else.

When he meets the adult Judy for the first time, Dexter’s heart “turned over like the fly-wheel on the boat.” This simile employed by Fitzgerald establishes a relationship between the actual realm and abstract realm, illusion, and reality, and inevitable disappointments and love.

The title of the story refers to the desire for affluence and status. It suggests the snowy barrenness and also sets the gloomy tone of the story that unfolds. During the season of dormancy and death, Dexter forms the greatest goals of his life. Over here, Fitzgerald employed an irony suggesting that these goals will not be affirming as imagined by Dexter.

Both structurally and symbolically, winter is important to the narrative. When the story begins, it is winter, and when it ends, it is again winters. This suggests the whole journey of Dexter from ambitious youth to a successful businessman is in the form is a natural cycle, 

At the beginning of the story, the winters in Minnesota are described as something like a white lid of the box that leaves everything covered in snow. This site of snow, though, offends Dexter as the site of so much activity turns desolate, he passionately skies over the course. 

At this time, golf represents a part of the rarefied world, and he feels a part of it. However, the world only exists in summer. Just like his relationship to the golf course, the winter dreams of Dexter also appear to be delusional.

Abstract ideas and concepts in a literary text are represented by objects, characters, and figures. The following are the symbols in the short story “Winter Dreams” by F. Scott Fitzgerald.

In the story, the boat is not only the symbol of luxury but also shows that indulgence and emptiness in life lead to. The boat is a very prominent and memorable entrance in the story. When Dexter is enjoying the peaceful moment and solitude on the raft, Judy approaches him in her boat.

Dexter is lost in a dream and filled with the bliss of arrival as he has finally achieved the success he dreamt of long ago. At that moment, he is entertaining the most favorable of predictions when he looks forward to the future. Dexter is feeling a kind of satisfaction and contentment that he never experienced again with that intensity.

The roaring motor overpowers the thoughts of Dexter about the charming and prospering life ahead and abruptly interrupts his musing. Judy’s arrival in the boat foreshadows the profound ways that will impact the future happiness of Dexter through the ensuing passion of Dexter.

The boat functions as an escape from reality for Judy. Her suitors and admirers quickly learn that she is too fast to clasp and only lives for the sake of her own pleasure. When she tells Dexter to drive the boat for her, Dexter obeys her. It is the first of the series of commands that he will obey.

The boat is an object of wealth and affluence and suggests how remote Judy is from reality. Judy tells Dexter that she has abandoned men who idealize her and drive her boat to the raft. Thus one can say that the boat is her source of escape in which the opposite gender tries to fit her in their dreams and reflect their idealized visions of a perfect woman. 

Likewise, when she gets bored with the man in New York, she hides again in the boat. The boat appears to be the refuge for Judy from the men’s oppressive affections. It is an expensive toy that removes her from any commitment or responsibility for her actions.

The golf balls are part of the luxurious world of the country club. It symbolizes the harm of the idle life and severe requirements that one must adapt to so as to show that they belong to the upper class of society. Dexter is a self-made businessman. However, he desperately tries to acquire the habits of the upper class and blend with this affluent world.

The imagery of the golf ball appears twice in “Winter Dreams.” Both of the time, the imagery mirrors the ease of the upper-class that the game embodies. The golfers use red and black balls before the spring defrosts in the North Country. The red and black balls stand out in the patches of snow on the course. 

This imagery comes first in the story when Dexter is in his teens and works as a caddy. He is excluded from Judy Jones and her set only because he belongs to the middle-class and has limited resources. However, when he becomes a successful businessman, he sacrifices his own identity and individuality for the white balls he uses.

The tone of the short story “Winter Dreams” is wistful and nostalgic. For example, the wistful and nostalgic tone of the short story is depicted in the story when Dexter steals a date with Judy in section three:

“During dinner [Judy] slipped into a moody depression which gave Dexter a feeling of uneasiness. Whatever petulance she uttered in her throaty voice worried him. Whatever she smiled at — at him, at a chicken liver, at nothing — it disturbed him that her smile could have no root in mirth, or even in amusement.”

 The response of Dexter matters more than the reason for Judy’s sadness as it gives out important information about the character. Dexter has a feeling that something is wrong but is unable to figure out what is wrong. The issue is Dexter is not able to understand Judy, and that appears to be sad. Though he longs for her, he can never get her.

The language of the passage is worried, uneasy, and disturbed, and it makes the readers feel like they do not know what is going on. Fitzgerald’s use of such language makes the readers really anxious. However, he intently uses these words so as to reinforce the idea that Dexter will long for her but will never get her. 

Another example of this wistful tone is:

“The dream was gone. Something had been taken from him. In a sort of panic, he pushed the palms of his hands into his eyes and tried to bring up a picture of … her mouth damp to his kisses and her eyes plaintive with melancholy and her freshness like new fine linen in the morning. Why, these things were no longer in the world! They had existed and they existed no longer.”

There are repeated words such as “taken,” gone,” and “no longer” in the passage, which shows the wistful tone of the short story.

The genre of the short story “Winter Dreams” is literary fiction and coming-of-age. The story starts when Dexter Green, the protagonist of the novel, is fourteen years old. When the story ends, he is thirty-two years old. However, his coming-of-age experiences are not something positive. He has compromised his dreams and faces the resentments to lose his ideals.

The main interest of the story is in the psychology of Dexter Green, which indicates that the short story “Winter Dreams” is literary fiction. The melancholic tone and careful style of formal storytelling of Fitzgerald belong to the genre of literary fiction. 

Both structurally and symbolically, winter is important to the narrative. When the story begins, it is winter, and when it ends, it is again winters. This suggests the whole journey of Dexter from ambitious youth to a successful businessman is in the form is a natural cycle,

At the beginning of the story, the winters in Minnesota are described as something like a white lid of the box that leaves everything covered in snow. This site of snow, though, offends Dexter as the site of so much activity turns desolate, he passionately skies over the course. At this time, golf represents a part of the rarefied world, and he feels a part of it. However, the world only exists in summer. Just like his relationship to the golf course, the winter dreams of Dexter also appear to be delusional.

There are three main settings of the short story “Winter Dreams.” These are Black Bear, Minnesota, Sherry Island Golf Club, and New York.

Most of the action of the story happens at the Sherry Island Golf Club. It is the place when young Dexter sees young Judy Jones for the first time. It is the place when Dexter sees Judy as an adult for the second time, and he falls in love with her. It is the place where Dexter observes the lifestyle of rich and famous people and wants to attain the same lifestyle for himself.

The Sherry Island Golf Club is the best place for the story. For instance, the natural beauty and loveliness of the place link the notion of money and beauty together in the mind of young Dexter. He always thinks that where there is beauty, there is cash.

Moreover, Shelly Island also lets the readers imagine the class issue with respect to geography. For instance, the narrator mentions that Dexter belongs to Black Bear place; however, there is no description of the place. In Dexter’s imagination, the place has no significant importance. However, Dexter pays more importance to Sherry’s Island as the place is inhabited by rich people. 

The place makes Dexter feel like “magnificently attune to life, radiating brightness and glamour he might never know again.” It is the place where Dexter goes while dreaming of improving his financial standing and social life.

Moreover, Sherry Island is near to the place where Dexter grows up. This fact constantly reminds Dexter of his own class and background: though he is from the middle-class, he has a humble origin. Dexter wants to spend his time at Sherry Island, but he is never able to forget his background. Even though he becomes excessively rich, he still does not belong to the rich world that is symbolized by Sherry Island.

Fancy New York

New York City represents richness as symbolized by Sherry Island. Dexter starts in Minnesota, however, leaves the town and starts living in New York. Minnesota is the native town of Fitzgerald. He is well aware of the class and social difference between New York and St. Paul

Writing Style

The writing style of the short story is straightforward and lush. The short story moves between the relatively straightforward dialogues and descriptions and beautiful imagery. The dialogues between Dexter and business associates let his nightmare swim off Island as:

“The tune the piano was playing at that moment had been gay and new five years before when Dexter was a sophomore at college. They had played it at a prom once when he could not afford the luxury of proms, and he had stood outside the gymnasium and listened. The sound of the tune precipitated in him a sort of ecstasy, and it was with that ecstasy he viewed what happened to him now. It was a mood of intense appreciation, a sense that, for once, he was magnificently attuned to life and that everything about him was radiating brightness and glamour he might never know again.”

This short passage contains the gist of Fitzgerald’s writing style in the story. The passage gives a strong feeling of passing the time. While listening to the music standing outside the gymnasium and listening to the inside activities, Dexter thinks of the prom held five years ago.

Putting differently, Dexter is looking back to the time when he was on the verge of financial success, both literally and symbolically. He was outside the social sphere of college, and now he is actively participating in the rich social activities. The music makes him remember his place five years ago and now how far he has come. This style also contributes to the wistful and nostalgic tone of the short story.

The passage also deals with how Dexter links social success and wealth with natural beauty. Dexter feels like he is beautiful when he is around rich people. He feels wonderfully acclimatize to life when he sits in darkness and listens to music. For him, everything in the Sherry Island appears to radiate a “ brightness and a glamour he might never know again .”

The words such as “brightness,” “glamour,” and “ecstasy,” and the rich language of the passage depicts the beauty that Dexter links with the wealth and rich life. The passage is quite wordy and descriptive as it gives the readers some idea of the artistry that Dexter fantasies his wealth will provide. He really hopes for a high life.

Such moments sharply contrasts with the ordinary conversation that Dexter has with his partners at the golf club or with his business associates Devlin. The romantic idealism of Dexter comes from his own imagination as the actual interaction with rich people is extremely dull. 

In “Winter Dreams,” these people lack the fertility of these descriptive moments. To emphasize the difference between the dull reality of the business world and Dexter’s dreams in this world, Fitzgerald uses the contrasting straightforward and rich style.

Narrator Point of View

The short story “Winter Dreams” is narrated in third person point of view. The narrator of the story is limited and omniscient. The narrator talks about the life of Dexter Green as a third person. The narrator only emphasizes the impression, thoughts, and memories of Dexter only and gives detailed descriptions of his thoughts and impressions.

Even though the story is not narrated from the first-person point of view, the only three-dimensional character of the story is Dexter. This is why the narrator is called a limited omniscient. The narrator knows everything; however, his knowledge is restricted to only one person, and that is Dexter Green. All of the other characters appear to be flesh out of the character of Dexter, even the character of Judy Jones.

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analysis essay on winter dreams

Winter Dreams

F. scott fitzgerald, ask litcharts ai: the answer to your questions.

Fourteen-year-old Dexter Green is a caddie at the Sherry Island Golf Club, a popular summer destination for the wealthy citizens of Black Bear, Minnesota. Throughout the year, Dexter occupies himself with memories of previous summers at the club and looks forward to the next summer there. He is particularly lost in reverie during the Midwestern winters, which are long and dreary and leave the golf course covered in deep mounds of snow. His memories of summers at the club are often blended with “ winter dreams ,” including fantasies of being a man as prominent as Mr. Mortimer Jones , but even more wonderful, and an even better golfer than the club’s best athlete, T.A. Hedrick .

One day, Dexter has his first conversation with Mr. Jones, after Jones learns that Dexter will quit caddying at the club. What Mr. Jones does not know is that Dexter is quitting due to an incident on the course with Jones’s “beautifully ugly” eleven-year-old daughter, Judy Jones , which left Dexter feeling insulted.

The narration skips ahead nearly a decade. Dexter has returned to the golf club, but he now is playing on the course. He left Black Bear to go to an “older and more famous university in the East,” instead of the state university where he had expected to take “a business course.” He returns home to open a small laundry, which he expands into a chain of laundries. This makes him, at twenty-seven years old, the owner of “the largest string of laundries in his section of the country.”

While on the golf course, he reunites with Judy who, according to Dexter, has grown into an “arrestingly beautiful” twenty-year-old woman. Through his golfing companion, T.A. Hedrick (with whom he is now unimpressed), he learns about Judy’s reputation for promiscuity. Later that evening, while swimming in the lake, she comes upon him in her motor-boat and introduces herself. She invites him to dinner at her house the next evening, and Dexter envisions Judy in a glamorous evening gown with a butler presenting cocktails, though neither of these things happens.

During dinner, Dexter talks about his years at university and his newly found wealth, which puts Judy at ease. She dismissed her last beau after finding out that he was poor. Judy decides rather quickly that she has fallen in love with Dexter and he returns her affections, but soon doubts her sincerity after seeing her go off with other men. Their relationship is characterized by moments of intense ardor followed by a cooling of affections. Dexter asks Judy to marry him. She half-heartedly accepts, then becomes involved with a New Yorker whom she promptly dumps.

After Judy leaves town to travel, Dexter becomes engaged to someone else, Irene Scheerer , a “light-haired…sweet and honorable” girl whose family welcomes him. Still, he persists in thinking about Judy who “had treated him with interest, with encouragement, with malice, with indifference, with contempt.”

A week before announcing his engagement to Irene, he sees Judy again at a dance at the University Club. Her absence had allowed Dexter to believe that he could move on, but once he sees her again he is “filled with a sudden excitement.” They leave the dance in her coupe and spend the night together. He quickly breaks his engagement to Irene to become engaged to Judy, a commitment that lasts only for one month.

After several years of entertaining the possibility, he decides to sell his laundries and move to New York. His plans are briefly interrupted by the First World War, which he enters as an officer, but he finally moves back East.

The narrative relates a final incident in Dexter’s life which occurs when he is thirty-two. He has a visitor from Detroit, Devlin , a business associate who knows Judy, as he is best friends with her husband, Lud Simms . Judy moved to Detroit to be with Simms who “drinks and runs around,” despite her and their children. Dexter is surprised by the news and even more surprised by Devlin’s assessments of Judy – that she is too old for Simms and that her looks have faded. The knowledge is devastating and Dexter suddenly feels “[f]or the first time in his life…like getting very drunk.” The destruction of his illusion of Judy, whom he saw as an emblem of great beauty and a representation of the rarefied social world that he had strived to join, results in the evaporation of his winter dream. He watches the sun set and, with the loss of the day, feels the loss of his youthful ideals, which no longer seem to matter.

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Short Stories of F. Scott Fitzgerald

By f. scott fitzgerald, short stories of f. scott fitzgerald summary and analysis of "winter dreams".

Dexter Green is fourteen at the beginning of the story. His father owns the second-best grocery store in town and he works as a caddy at the golf club for pocket money.

The effect of winter on Green’s psyche is intense. He lapses into "profound melancholy." It appears that winter severely affects Green’s mental state: it makes him "tremble," "repeat idiotic sentences" and "command…imaginary audiences." In winter, he hallucinates – initially about golf games, which he plays "over the fairways of his imagination."

Fourteen-year old Dexter Green encounters an eleven-year old spoiled brat who instigates him handing in his notice at the golf club. She is Judy Jones – described as being unattractive in a way particular to ugly ducklings who are soon to grow into beautiful swans. Miss Jones is determined to get what she wants: Green to wait on her as her caddy. She drops her bag and marches off across the course. He quits his job rather than wait on her, a decision that surprises him as much as his employer.

Green’s desires are not to just be close to wealth, but to have it. He makes a success of a laundry business. He joins the golf club as a member at 23 and finally beats Mr. T A Hedrick, his opponent in his many fantasies. In so doing, however, he learns that Hedrick is dull and a poor golfer.

When he sees Judy again, she is playing golf and hits Mr. T. A. Hedrick in the abdomen with a ball. She shows no remorse. She is now beautiful, and he is immediately taken with her.

Green is later disturbed from a reverie at the beach by Judy Jones on her boat. She asks him to drive it so she can surf behind the boat. She loves the speed, and Green is captivated by her.

Judy invites Green to dinner. His background forces him to consider what he wears, as he does not have the security of ancestry to allow him to dress carelessly. Judy tells him that she has discovered that the man she is in love with is actually poor, though he had made the pretense of not being so. She is impressed that Green is wealthy and kisses him passionately.

Green is swept up in her and bends to her every whim. She, however, has a succession of suitors, which Green finds painful. But because he was so devoted to Judy, she began to take him for granted. Keen to change this, Green becomes engaged to another girl, Irene Scheerer. Despite his imminent marriage to Irene, his passion for Judy remains. When Judy says “I wish you’d marry me,” Green is confused. He does not tell Judy about Irene, and resumes his relationship with Judy.

Judy and Green are together for only a month. Even on reflection, it still takes Green a long time to actually regret this decision. His relationship with Irene is over, as is his friendship with her family. He finally understands that he loved Judy but could not have her. Green sells up his businesses and goes to war, in an attempt to escape his feelings.

Seven years later, Green is talking to a business acquaintance when Judy’s name comes up. She is now Judy Simms; unhappily married to a brute who treats her poorly. When he is told also that Judy is no longer beautiful, Green is distraught. The version of Judy, young and beautiful, who he had loved, was no longer real.

Green seems to have a compulsion to act in certain ways around women – Judy Jones in particular – although there is no consistency in his responses. Green refuses to caddy for Judy on their first childhood meeting, but is then compelled to give in to her at every other opportunity. It is clear that he wants to possess Judy, rather than just love her. As with many of Fitzgerald’s protagonists, "he wanted not association with glittering things and glittering people – he wanted the glittering things themselves."

When Green hears the tune from his prom, he is at his happiest. It is before Judy has drawn him in fully, and he remains an optimistic and confident young man, "magnificently attuned to life, and …everything about him was radiating a brightness and glamour he might never know again." These words are ironic as he is never again this assured of himself. As Green drives the boat for Judy, he is as zealous in his feelings as he was the first time they met; illustrated by the simile "his heart turned over like the fly-wheel of the boat." His reactions to Judy do seem somewhat mechanical, in that he seems to react involuntarily to her.

Judy epitomizes the tragic beauty of the age when she expresses her frustration at her loneliness – ‘“I’m more beautiful than anybody else,” she said brokenly, “Why can’t I be happy?”'

Green’s deep regret is that he will never possess Judy: "He loved her, and he would love her until the day he was too old for loving – but he could not have her." This causes him to "taste…deep pain," just as he had experienced "deep happiness."

When Green’s dream is "taken from him," his disappointment is not in learning that Judy is unhappy. Green had cherished his idea of Judy as perfect, beautiful, unattainable. But, as Gatsby learns upon reunion with Daisy that "no amount of fire or freshness can match what a man will store in his ghostly heart," Green is crushed to learn that Judy was no longer the girl he loved. It is similar to his experience golfing with Hedrick, who turned out to be a mediocre opponent after years of dreaming of defeating him. With the knowledge that Judy's beauty had faded, for Green it was as if she had died.

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Short Stories of F. Scott Fitzgerald Questions and Answers

The Question and Answer section for Short Stories of F. Scott Fitzgerald is a great resource to ask questions, find answers, and discuss the novel.

What is the them of this short story

I'm sorry, which of Fitzgerald's short-stories are you referring to? In addition, did you mean "them" as written above or theme?

Winter Dreams

Dexter's interest in Judy has as much to do with fulfilling his own aspirations, as it does to his attraction to her. Dexter is no longer smitten, but rather, determined. He doesn't want Judy merely because she has a pretty face, but rather,...

Dexter opens a successful laundry business and acquires wealth... he also becomes a member of the golf club.

Study Guide for Short Stories of F. Scott Fitzgerald

Short Stories of F. Scott Fitzgerald study guide contains a biography of F. Scott Fitzgerald, literature essays, quiz questions, major themes, characters, and a full summary and analysis of selected short stories.

  • About Short Stories of F. Scott Fitzgerald
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  • Character List

Essays for Short Stories of F. Scott Fitzgerald

Short Stories of F. Scott Fitzgerald essays are academic essays for citation. These papers were written primarily by students and provide critical analysis of F. Scott Fitzgerald short stories.

  • Negative Views on Memory in "Babylon Revisited"
  • The New Woman of the 1920's in 'Winter Dreams' by F. Scott Fitzgerald
  • Fitzgerald's “Winter Dreams”: Chasing Dreams
  • Luminosity In "Winter Dreams": The Art and Elegance of Fitzgerald's Prose
  • Time Passes, and Much Else Changes: "The Curious Case of Benjamin Button" and Its Film Adaptation

Lesson Plan for Short Stories of F. Scott Fitzgerald

  • About the Author
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  • Introduction to Short Stories of F. Scott Fitzgerald
  • Relationship to Other Books
  • Bringing in Technology
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Wikipedia Entries for Short Stories of F. Scott Fitzgerald

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analysis essay on winter dreams

Winter Dreams

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Discussion Questions

Describe Fitzgerald’s use of paradox throughout the story. What subtext does it bring to the story?

How does Fitzgerald convey the disparity between dreams and reality—that is, the theme of illusion and disillusionment?

How would you describe Dexter’s winter dreams? Using evidence from the text, explain the content of Dexter’s winter dreams and what actions he takes to pursue them.

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  1. Analysis of F. Scott Fitzgerald's Winter Dreams Essay

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  2. "Winter Dreams" by F. Scott Fitzgerald Analysis

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  1. Analysis of F. Scott Fitzgerald's Winter Dreams

    By NASRULLAH MAMBROL on April 27, 2022. Winter Dreams presents situations and themes that would preoccupy F. Scott Fitzgerald's famous novel The Great Gatsby, which also embodies American aspirations for social legitimacy and existential self-worth in the form of a longing to possess a desirable woman. Much like that work's, its account of ...

  2. Winter Dreams Study Guide

    Key Facts about Winter Dreams. Full Title: Winter Dreams. When Written: 1921-1922. Where Written: St. Paul, Minnesota. When Published: December 1922 in Metropolitan magazine; February 1926 in Fitzgerald's third volume of stories, All the Sad Young Men. Literary Period: Modernism.

  3. Winter Dreams Analysis

    In ''Winter Dreams,'' Fitzgerald does not name his character, but his presence is felt nevertheless. The first time his voice emerges is at the opening of Part II, where he tells readers ...

  4. "Winter Dreams", analysis of the story by Fitzgerald

    Published in 1922, Winter Dreams is a play on the American Dreams ideal perpetuated in that era and is a study of class, aspirations and relationships and obsessions through infatuation. Dexter Green is the character around which the story is based. Son of a grocer in Minnesota, Dexter caddies at the local golf course during the Summer months ...

  5. "Winter Dreams" by Scott Fitzgerald: Analysis

    Major Themes in "Winter Dreams" by Scott Fitzgerald. 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.

  6. Winter Dreams by F. Scott Fitzgerald: Analysis

    Fitzgerald wrote his short story "Winter Dreams" while he was drafting The Great Gatsby, which became one of the most celebrated novels of all time. ... Presenting Analysis, Context & Criticism on Commonly Studied Short Stories, Volume 15, F. Scott Fitzgerald, Published by Gale, 2002. Wendy Perkins, Critical Essay on "Winter Dreams," in ...

  7. PDF ANALYSIS "Winter Dreams" (1922)

    ANALYSIS "Winter Dreams" (1922) F. Scott Fitzgerald (1896-1940) ... New Essays on . The Great Gatsby (Cambridge U 1985) 10-11 "It is not until 'Winter Dreams' in 1923 [1922] that Fitzgerald explicitly connects the themes of love and money. In this story, Dexter Green, a figure straight from the work ethic of Horatio Alger, loses Judy

  8. Winter Dreams Section 1 Summary & Analysis

    Winter Dreams: Section 1 Summary & Analysis. While some of the other caddies at the Sherry Island Golf Club are poor, Dexter Green 's father owns the second-best grocery store in Black Bear, MN. Dexter, therefore, caddies every summer for the wealthy patrons of the Sherry Island Golf Club not because his family needs the income, but rather ...

  9. Winter Dreams Story Analysis

    Analysis: "Winter Dreams". "Winter Dreams" takes place mostly in Minnesota, which is known for its cold, gloomy winters. The title evokes longing for the spiritual rebirth associated with spring: "Winter dreams" look forward to glistening light and warmth amid the dullness of winter. The story unfolds in the third-person limited ...

  10. Winter Dreams Summary and Complete Study Guide

    These "winter dreams" are also known as the American Dream. Even though Dexter attains great success and becomes a successful businessman, he pays a great price for it. The social mobility that Dexter attains as a result of wealth, it heavily restricts his capacity for happiness. Dexter comes from a humble background.

  11. Winter Dreams Essays and Criticism

    Analysis PDF Downloads Lesson Plans ... Source: Wendy Perkins, Critical Essay on ''Winter Dreams,'' in Short Stories for Students, The Gale Group, 2002. Perkins is an instructor of English ...

  12. Winter Dreams Full Text and Analysis

    F. Scott Fitzgerald's "Winter Dreams" initially appeared in the periodical Metropolitan in 1922, during the peak of the American Modernist period that would last until the end of World War II. Considered one of Fitzgerald's greatest short stories, the narrative explores the painful loss of romantic illusions through his portrayal of Dexter Green's struggle to acquire wealth and ...

  13. Winter Dreams by F. Scott Fitzgerald Plot Summary

    Winter Dreams Summary. Fourteen-year-old Dexter Green is a caddie at the Sherry Island Golf Club, a popular summer destination for the wealthy citizens of Black Bear, Minnesota. Throughout the year, Dexter occupies himself with memories of previous summers at the club and looks forward to the next summer there.

  14. Short Stories of F. Scott Fitzgerald "Winter Dreams" Summary and

    Short Stories of F. Scott Fitzgerald essays are academic essays for citation. These papers were written primarily by students and provide critical analysis of F. Scott Fitzgerald short stories. Negative Views on Memory in "Babylon Revisited" The New Woman of the 1920's in 'Winter Dreams' by F. Scott Fitzgerald

  15. Winter Dreams Themes

    Discussion of themes and motifs in F. Scott Fitzgerald's Winter Dreams. eNotes critical analyses help you gain a deeper understanding of Winter Dreams so you can excel on your essay or test.

  16. Themes in Winter Dreams

    The conflict between romantic illusion and reality is a major theme in the story. Dexter's youthful illusions about the elite upper class and his associating it with grace, style, beauty, glamour, and excitement have faded with his exposure to it through his relationship with Judy once he had become a financial success. However, he fails to ...

  17. Winter Dreams Essay Topics

    for only $0.70/week. Subscribe. By F. Scott Fitzgerald. Thanks for exploring this SuperSummary Study Guide of "Winter Dreams" by F. Scott Fitzgerald. A modern alternative to SparkNotes and CliffsNotes, SuperSummary offers high-quality Study Guides with detailed chapter summaries and analysis of major themes, characters, and more.

  18. Winter Dreams, F. Scott Fitzgerald

    Winter Dreams, F. Scott Fitzgerald - Analysis. F.Scott Fitzgerald's "Winter Dreams" documents the life of Dexter Green, "a young man from a modest background who strives to be a part of the exclusive world inhabitated by the women he loves" (Perkins 1). The work regards a period in Dexter Greens life, from the age of fourteen to ...