"Winter Dreams" (easier PDF version to read)
Study Questions for "Winter Dreams"
One. How does the story introduce social class anxieties into Dexter’s personality?
Dexter’s dad is “second best,” the owner of a second best grocery store, evidencing working class roots.
Dexter works as a caddie, a servant to the upper classes, and he finds this humiliating.
He reads the bleak weather as an omen of his doom while living in the underclass, working as a servile caddy for professional players and tastemakers, people who matter.
He feels irrelevant and irrelevance stirs resentment and depression in his veins.
He sees life as extremes, those who have and those who have not; the dreary Northern spring and the gorgeous fall.
He creates this false binary universe: We call this the All or Nothing Fallacy.
After the depression of spring, October brings him hope and November brings him “ecstatic triumph.”
We see Dexter’s vaulting ambition to get away from the lowly caddy job. He’s “too old” for it, he thinks, at 14.
Two. What compelled Dexter to hurry away from his caddy job?
An 11-year-old girl, Miss Jones, described as “beautifully ugly” and “who are destined after a few years to be inexpressibly lovely and bring no end of misery to a great number of men.”
Indeed, beauty can unhinge men and dislocate men from reality, as we shall see in the story.
But not just beauty—beauty combined with the aura of upper class money: This is the noxious cocktail that will undermine Dexter Green.
The girl addressed Dexter as “boy,” a sign of his lowly servitude, and this has an emasculating effect on him.
His sense of emasculating is further reinforced when the caddy-master shows up and says to Dexter, “What you standing there like a dummy for? Go pick up the young lady’s clubs.”
He quits from compulsion: “The enormity of his decision frightened him. He was a favorite caddy, and the thirty dollars a month he earned through the summer were not to be made elsewhere around the lake. But he had received a strong emotional shock, and his perturbation required a violent and immediate outlet.”
His perturbation is the great anxiety that makes him compulsive and unhinges him. He’s high-strung and compulsive.
We read a warning of his compulsive nature: “As so frequently would be the case in the future, Dexter was unconsciously dictated by his winter dreams.”
Three. We read a famous passage: "But do not get the impression, because his winter dreams happened to be concerned at first with musings on the rich, that there was anything shoddy in the boy. He wanted not association with glittering things and glittering people -- he wanted the glittering things themselves.” What does this passage mean?
Dexter believes he can, through hard work, embody “glitter,” that is to say the apotheosis of success. America is not a country; it’s a dream. America is “Winter Dreams,” the idea that we find personal fulfillment, meaning, and higher purpose through the attainment of “glitter.” It is this very sick idolatry that will undermine Dexter Green.
We also read that while he become successful in business, he suffered certain “denials,” and that the story is about one of those denials, and that would be the denial of acquiring Judy Jones, who for Dexter is the highest example (apotheosis) of “glitter,” of Dexter’s “Winter Dreams.”
Four. As we read about Dexter’s rise in the laundry industry and the rich patrons who frequent his establishments, we learn what about old and new money?
Old money has a certain aura, a certain “heritage,” and a snobbery attached to it. On the other hand, new money, the rags to riches story such as Dexter’s, has humble beginnings and class insecurity attached to it even as the person of new wealth amasses riches because in part he will always feel a bit like a fish out of water and he will always have memories of his poor beginnings. Moreover, he may not know all the codes and linguistic tics that the old rich use in their arsenal of being smugly rich. He may have some of his old caddy behaviors, which he thinks about when he returns to play golf at his old course—not as a caddy but as a man who’s “made it.”
We can surmise perhaps that Dexter is not just desperate to be rich but is desperate to have an identity of being rich, of not being looked down upon by those with old money, and his delusion is that winning the affections of old-money Judy Jones with all her intoxicating beauty is his ticket to happiness.
But much of his quest is in his own imagination. Therefore, his quest is an illusion or a chimera, and it is this chimera that will unhinge him.
Five. One of the brilliant things in this story is the way Fitzgerald quickly exposes Judy Jones’ personality at the golf course where she hits a golf ball into Mr. T.A. Hedrick’s abdomen. What do we learn about her in such a brief passage?
Judy Jones is self-centered, entitled, and used to not being accountable for anything. In other words, she is somewhat of a cipher and wastrel. She makes messes and expects others to clean them up. She can hurt others, but feel no empathy for her actions. In other words, she’s an empty-headed, repellant narcissist.
And here lies the story’s tragedy: Dexter Green has hinged is whole notion of happiness on going on a Love Quest for Judy Jones, a Narcissistic Cipher. His “winter dreams” are futile, delusional, and empty. They will bring him nothing but a handful of ashes and dust.
Another important observation from this scene is that Dexter watches the old-money golf players gawk and admire Judy Jones’ beauty, doing so with a certain misogyny and lasciviousness.
Their remarks make her all the more a compelling “trophy.” Dexter is diseased by the need to create an image through the amassing of trophies, what in Latin is called the libido ostentando. Dexter’s lust for ostentatiousness will blind him from the fundamental emptiness that defines his existence.
Six. After seeing the adult beauty Judy Jones at the golf course, Dexter goes on a night swim and hears piano that he associates with the correct life path he has taken: “The sound of the tune precipitated in him a sort of ecstasy and it was with that ecstasy he viewed what was happening 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 a brightness and a glamour he might never know again.”
How does the above passage speak to The Trickster as part of Dexter’s Quest to find his Winter Dreams?
“Winter Dreams” is essentially a chimera story: A man quests for his chimera and is crushed by the emptiness of his dream. Therefore, a chimera can be called a Trickster. A Trickster is a character or an idea that carries us through the four levels of emotion: earthly, angelic, mystical, and demonic.
The Trickster must give us hope and promise of finding a land of milk and honey only to throw us down from the heavens and into the inferno of our own making.
Seven. In Part III, how do we see Dexter as a committed student of social class?
While Dexter asserts his superiority over the old-money rich due to his hard work ethic, he wants his children to grow up as old money, and Dexter wants to learn the codes of old money: casual dress, facial expressions (hauteur and superciliousness), and all the consumer secrets the old rich enjoy. The rich have a secret code of conduct that sets them apart from the rest, and Dexter wants to be an expert on this code.
Dexter must “keep to the set patterns” so that his peasant background will never be revealed and thus bring shame to him and his future family.
Further, he lies about his origins, tells the rich he’s from Keeble, not the working-class Black Bear Village.
Eight. Even though Judy Jones is a flirt and a shallow coquette, she inadvertently asks Dexter an existential question during their first dinner: “Who are you, anyhow?” How does her question touch on one of the story’s major themes?
As an American, Dexter believes he can re-invent himself anyway he wants. He is a chameleon, and he is free to dream himself into the kind of person he wants to be. The idea that we can become our dream is uniquely American.
The irony is that in many ways he doesn’t know who he is since his energies have created a façade to others and to himself.
In fact, his answer to Judy’s question is unwittingly true. He says, “I’m nobody. . . . My career is largely a matter of futures.” In fact, he only lives in the future, not the present, and this is part of his unhinged character: to be disconnected and disengaged from the present as he looks to the future when he will finally be worthy of achieving the American Dream. But he will never be worthy. His hope is a chimera that pushes him to constantly look ahead into the future and never in the present moment.
When he assures Judy he is not poor and she kisses him, her kisses arouse a “surfeit that would demand more surfeit.” In other words, his desires will always outrun his capacity to fulfill them, and Judy Jones is the embodiment of his excess desires or concupiscence.
What we have, then, is a mutually self-destructive symbiosis or interdependence. What’s scary is that that unhealthy symbiosis is the very foundation of Dexter’s “Winter Dreams.”
Nine. Much of the story chronicles Dexter’s addiction to Judy Jones like a junkie hooked on drugs. Explain.
We read, “Dexter surrendered himself to the most direct and unprincipled personality with which he had ever come into contact.”
The unhinged man is so needy and compulsive that he surrenders his self-interest to an unethical, morally bankrupt force in the name of his carnal and monetary idolatry.
He has no moral combat to save him from pursuing someone as unprincipled as Judy Jones.
We can further explore Dexter’s unhinging with Judy Jones by looking at her as a drug. She is less human to Dexter and more of a substance of his addiction. And in turn Judy Jones is addicted to the power she has over men by her power to intoxicate them. She in turn is addicted to seeing men addicted to her.
We see that Dexter is no needy for Judy Jones that he sacrifices his dignity and self-respect to pursue her. For example, he knows she loves other men in her shallow capricious way and that she sometimes “loves” in the same pathetic, superficial manner, and she even tells him so, but rather than be upset he accepts her imperfect, disloyal love. We read, for example, that after telling him that she was in love with another man earlier the same day as they lie in bed, he finds her words “beautiful and romantic.”
When she lies to him and says she did not kiss a man earlier the same day, Dexter knows she’s lying, but he’s okay with that because he is “glad that she has taken the time to lie to him.”
Because Judy Jones is aware that he has no standards of behavior that she must adhere to, she knows she can get away with anything. Deep down, she can’t love him because he lacks self-respect, but she herself lacks self-respect because if she had it, she would not be in a relationship with someone she doesn’t respect. Both of them are degraded in the relationship, a fact that neither wants to see. Both are unhinged in this manner.
As you read the story, you will see that the narrative has many parallels with drug addiction as it pertains to Dexter Green’s relationship with Judy Jones.
Over and over again, we see that Judy Jones, the consummate Trickster, sends Dexter into hell through neglect and infidelity, but then gives him just enough honey so he’ll come back to her. She does this to many men, not just Dexter. We read, “Whenever one showed signs of dropping out through long neglect, she granted him a brief honeyed hour, which encouraged him to tag along for a year or so longer.”
She is clearly a sick person and the men who become addicted to her are just as sickly. They live in a demimonde of no-respect and emptiness.
Like a drug addict, Dexter becomes unhinged and cannot be civil to others when she unexpectedly disappears at a social event. He panics and is overcome with anxiety that causes him to lose his polite facade.
We read that Judy Jones is not a self-possessed person in her compulsion to torture men: “Judy made these forays upon the helpless and defeated without malice, indeed half unconscious that there was anything mischievous in anything that she did.”
Even the “strong and the brilliant, “play her game and not their own.” She always has the upper hand.
Her beauty is her power, but as we shall see, using beauty for power and identity is a sure failure because beauty is transitory.
For example, I know a man who used to look like Paul McCartney, but as this celebrity wannabe aged, his face bloated and his distorted features no longer gave him the cachet he enjoyed in his youth. He now lives in his mother’s basement where he traipses around in a robe and eats Hot Pockets while trolling on the Internet.
But while her beauty is in its prime, she is Dexter’s drug, as we read: “The helpless ecstasy of losing himself with in her was opiate rather than tonic.”
When you think about the above line, many of us love the drama of a tormented obsession, and we therefore choose to stay entrapped in our torment because to lose that drama would force us to face the abyss or the existential vacuum that defines our empty existence.
In many ways, the story teaches us that we are our own worst enemy. Sadly, many of us “unhinge” ourselves from reality for lack of anything better to do.
Another way of looking at Dexter’s “Winter Dreams” is that he was feeding off the sick energy of desperation that Judy Jones created between her and her bevy of lovers.
Dexter knows he’s an addict, at least on an unconscious level. This makes him a divided soul: Part of him wants to escape his addiction to Judy Jones. He even gets engaged to another woman as a hopeful “cure” for his disease. Imagine getting engaged to someone you don’t love as a “cure” for a love addiction. That is a cogent sign of being unhinged.
His Judy Jones substitute is Irene Scheerer. Unlike Judy Jones who is described as a refined beauty, we read little of Irene’s physical charms except that she is “a little stout.”
We have to wonder if the world is full of Judy Jones archetypes that enchant men, leave them, and damage the men so that they can never love other women because these damaged men are forever fixated on their own personal “Judy Jones.” Perhaps we can call this the Angelina Jolie Factor: One look into her eyes and you’re permanently damaged, unhinged, and ready to abandon reality as you know it.
Even as he tries to love Irene, he keeps thinking about the manner in which Judy Jones beckons, torments, and insults him, and he is desperate to convince himself that he cannot pursue Judy Jones any longer. But as an unhinged man, as a man possessed by the IDEA of what Judy Jones represents—complete power, ecstasy, and abandonment—he finds his drug addiction incurable, and as such he hates himself and he hates Judy Jones—the very woman he cannot free himself from.
At night, he argues with himself about Judy Jones, going over a laundry list as to why she’d be a horrible wife. But that is the cortex in his brain. The limbic part of his brain, where emotion and reptilian desire reside, continue to rage a protest for acquiring Judy Jones.
He sees Judy Jones at a dance and he realizes that he had long ago been “hardened against jealousy.” He still wants her. He’s twenty-five, he has devoted 14 years to obsessing over Judy Jones, and he is about to marry Irene Scheerer.
About to get married to Irene, he still obsesses over Judy Jones, wondering if she still cares about him, and Irene is nothing but a backdrop to his life, “no more than a curtain spread behind him.” She will be part of a marital façade, but his demonic possession will still rage on.
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