Can you explain Dexter's "winter dreams" in the story?

In “Winter Dreams” by F. Scott Fitzgerald, Dexter spends the winters of his youth musing over the lives of the wealthy members of the country club where he is a mere caddie. He sees himself playing matches with and against the club members, winning the club championship, and driving an expensive car. He longs not only to be like these men, he longs for the things they have. In his dreams, he is a man of prestige and accomplishment.

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 merely snobbish in the boy. He wanted not association with glittering things and glittering people—he wanted the glittering things themselves.

Judy Jones enters his life when he is only fourteen years old, but she steers the course of his life into his thirties. His winter dreams focus on his obsession with this beautiful but fickle young lady. When he is with her, his dreams are fulfilled.

She simply made men conscious to the highest degree of her physical loveliness. Dexter had no desire to change her. Her deficiencies were knit up with a passionate energy that transcended and justified them.

Unfortunately for him, Judy moves from one man to the next without a thought for their feelings. As the seasons change, he begins to realize that he cannot have her and he tries to move on, even becoming engaged to another. “When autumn had come and gone again it occurred to him that he could not have Judy Jones.” But again, Judy appears and his stability is torn away once more. In spite of his success as a businessman who fulfilled his original winter dreams, Dexter is unable to let the dream of Judy die.

War intervenes, and upon his return, he builds his business in New York. During a business meeting, he learns of Judy's marriage. According to an acquaintance, she is in a difficult marriage, and her looks have dwindled. Only after hearing this does Dexter realize that although he attained his youthful “winter dreams,” he sold his soul for Judy Jones.

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.

"Long ago," he said, "long ago, there was something in me, but now that thing is gone. Now that thing is gone, that thing is gone. I cannot cry. I cannot care. That thing will come back no more."

Why does Dexter find spring dismal and fall hopeful in "Winter Dreams"?

Dexter finds the spring "dismal" because it means he must return to his work as a caddy, and abandon his "winter dreams." The fall, however, is "gorgeous" because then he can reflect on his "fleeting brilliant impressions" of summer and imagine himself, for example, a champion golfer, easily able to defeat the wealthy men for whom he caddies.

These "winter dreams" all have to do with the acquisition of things. The narrator explains that: 

He wanted not association with glittering things and glittering people—he wanted the glittering things themselves. 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.

Another way to understand the "dismal" nature of the spring is to associate it with the "mysterious" denials of real life. Dexter is a person who seems able to make his dreams come true; he becomes wealthy very young, and soon is living out his fantasy of playing at the club where he once caddied. Yet Judy Jones is one thing he cannot have. She is his most persistent "winter dream," a vision of loveliness that, like a dream, consistently eludes him. The reality of Judy is a bit more complicated, however. Whether Judy really is "the best" or not is beside the point—for Dexter, she is one of those "glittering things" he wants, and his inability to get her points out his own emptiness. The fact that Dexter desires her but cannot have her suggests that the "hope" he finds in the fall could be as empty as the "dismal" spring. 

In "Winter Dreams," what feelings does Dexter associate with each season?

The winter in Minnesota is bleak for Dexter; he describes living in it as "a feeling of profound melancholy." Nonetheless, it offers him time and solitude to reflect on the direction he wants his life to take.

Counterintuitively, spring, for Dexter, is no better; for him, there is "something dismal" about it.

The fall, October and November, "filled him with hope" and an "ecstatic triumph," and energized him greatly.

Summer is recalled as a "fleeting brilliant impression" that fed his grandiose imagination, but it is also the season that drives him to pursue the dreams he indulged in during winter: to do more than observe and cater to the rich—to become one of them. The day he quits being a caddy on the summer golf course changes the direction of his life. The imagined life he concocts in his winter dreams becomes his reason for being, and his wealth begins with the humble purchase of a laundry.

In "Winter Dreams," what feelings does Dexter associate with each season?

It is clear from the title of this excellent short story by Fitzgerald that the seasons, or at least winter, will have a serious role in the action. It is in the opening paragraphs that we are given a description of how the seasons impact Dexter and which seasons are more important to him. Note how the changing of seasons changes Dexter:

Dexter knew that there was something dismal about this Northern spring, just as he knew there was something gorgeous about the fall. Fall made him clinch his hands and tremble and repeat idiotic sentences to himself, and make brisk abrupt gestures of command to imaginary audiences and armies. October filled him with hope with November raised to a sort of ecstatic triumph...

It is clear then that fall, with the hope of the approaching winter, makes Dexter feel more than he is - it makes him feel that he is an important man of value and commanding respect and loyalty from "imaginary audiences." It is no wonder then that because of this affinity he has with winter that he chooses to attach his "dreams" to this season - cold and elusive as they will turn out to be.

Can you provide a direct characterization of Dexter in "Winter Dreams"?

Authors accomplish direct characterization when they closely describe characters's looks and traits. Sometimes it is the narrator who provides it, or it can be the words of another character in the work.

Dexter Green has a decisive and self-confident personality, seen first on the day that he abruptly quits his job as a caddy. He tells Mr. Jones, who pleads with Dexter to caddy for him, that "I decided I was too old." Dexter's winter dreams lead him to sidestep the then-conventional worlds of the stock market and sales to become a self-made businessman. He "borrowed a thousand dollars on his college degree and his confident mouth, and bought a partnership in a laundry."

Once Dexter has prospered, he returns briefly to the golf club where he had caddied as a boy and finds that he "was impressed by the tremendous superiority he felt toward Mr. T. A. Hedrick, who was a bore and not even a good golfer any more." Dexter has surpassed the men whom he had formerly held in awe.

Fitzgerald builds the characterization of Dexter Green through descriptions of his confident decision-making and unshakeable belief in himself. Dexter is widely regarded as a good catch because "he was an eligible young man, now, and popular with down-town fathers."

Can you provide a direct characterization of Dexter in "Winter Dreams"?

This is such a wonderful story. All of F. Scott Fitzgerald's writing evokes such clear images, and his characterization becomes very clear from his use of language. For example, as the narrator says, "as so frequently would be the case in the future, Dexter was unconsciously dictated to by his winter dreams.’’ Dextor is frivolous but maybe only in what he places value on. He cares for wealth, pretty girls, and status. This is played out in his relationship with Judy and the way he lives his life. His winter dream (his idea of a perfect life) emcompasses wealth, pretty girls, and status, and it is for that reason that he is chasing those things. This is why he takes the fact that Judy has lost her beauty so seriously. The loss of her beauty is the loss of his dream.

What do Dexter's dreams suggest about his future desires in "Winter Dreams"?

Dexter's "Winter Dreams" seem to focus on his obsession with being rich and embodying the trappings of wealth.  Growing up relatively middle class, he understands from an early age that there is "something different" about how the rich are.  He gains this insight from being their caddy.  His first exposure to Judy helps to reveal this, in terms of being able to possess an understanding that they carry themselves differently.  Dexter believes this is because they are rich.  His dream of gaining and being able to display his wealth manifests itself in being able to play in a foursome with the same people for whom he used to caddy, or being invited to an exclusive country club.  His dream lies in being able to "rub elbows" with those who are wealthy.  This might be why he is so captivated by Judy, as she is a part of this world.  The way in which she carries herself, interacts with men, and displays an attitude that poor people simply could not display is why he is so entranced by her. It is also the reason why he weeps at the end because she is so far removed from that world at the end of the story.

What are Dexter's feelings about winter in "Winter Dreams"?

Dexter's general feeling about winter is that it engulfs and shadows the beauty of summertime. In the story, we read that Dexter usually breaks out his skis when 'the long, Minnesota winter shut(s) down like the white lid of a box.' As he skis, he notices the remnant evidence of a summer past. It makes him sad and angry all at the same time; the destructiveness of winter haunts him, and he feels trapped.

At these times the country gave him a feeling of profound melancholy--it offended him that the links should lie in enforced fallowness, haunted by ragged sparrows for the long season. It was dreary, too, that on the tees where the gay colors fluttered in summer there were now only the desolate sand-boxes knee-deep in crusted ice.

In the story, this winter portrait foreshadows the loss of Dexter's dreams, of marriage to Judy Jones and of happiness in his personal life. Both his dreams and the delectable Judy's youthful beauty are destroyed by pain, suffering, and loss. Like the dreary Minnesota winter Dexter detests, the summer of young, infatuated love is but an illusion.