Dexter pursues his “winter dreams” as though they will come true exactly as he envisioned them at fourteen. While the dreams provide him with the drive to become successful, they never bring him happiness—if they come true, he is dissatisfied, and if they fail to materialize, he is unfulfilled. Therefore, for Dexter, happiness is always just out of reach. His inflexibility and his fixation on illusions of perfection prevent him from being satisfied with any aspect of his life.
Over the course of the story, several of Dexter’s winter dreams do come true. For example, he defeats T.A. Hedrick—the Sherry Island Golf Club’s best athlete—during a game of golf, which he had fantasized about since he was fourteen. However, the win is less satisfying than he had imagined, since his very ability to defeat Hedrick seems to signal to Dexter that Hedrick was not a worthy opponent. Instead of relishing his victory, Dexter dismisses Hedrick as a poor golfer and begins looking towards his next challenge that he thinks will satisfy him by proving his worth. Dexter’s constant reaching for the next rung of prestige and success is also evident in his college experience. His winter dreams dictate that he should go to a more famous university in the East instead of enrolling at a business course at the state university, as he originally intended. He is accepted to the school, which enables his dream of living among northeastern elites, but it’s not enough—once there, he cannot help but compare himself to other students who are wealthier than he. Though his father’s business is prospering and he is living a life about which he could once only fantasize, he is “bothered by his scanty funds.”
Despite that, time and time again, Dexter is dissatisfied by his dreams coming true, he never comes to understand that realizing his next goal might also leave him unfulfilled. In other words, Dexter is possessed by the dreams that remain unattained, obsessing over them rather than acknowledging reality and finding satisfaction with what is available to him. This is clearest in his relationship to Judy. Dexter wants to marry Judy because he thinks that she is the most beautiful girl in Black Bear. In his imagination, she is one of the “glittering people” he wants to become, and he thinks that, if he marries her, he will be happy. This erroneous belief causes Dexter to chase after her for most of his twenties, believing—despite all evidence to the contrary—that one day she will change her ways and commit to him. The destructive nature of this behavior is apparent when he breaks up with his fiancée, Irene, who is kind, wealthy, and stable. Though he finds Irene less exciting than Judy, he feels a “tranquility” with her that he knows could lead to domestic contentment. Despite this life being available to him, he throws it away to take one more chance with Judy, who then breaks up with him after a month.
Dexter’s inability to link his constant dissatisfaction with the pursuit of his winter dreams seems rooted in his fundamental inability to recognize happiness. During dinner at Judy’s home, for instance, he is “disturbed” to find on her face a smile that has “no root in mirth, or even amusement.” However, instead of understanding that this is a sign that something is wrong, her false smile only makes him want to kiss her. If Judy’s own happiness is only a front, then it’s delusional to think that marrying her would make Dexter happy. However, Dexter doesn’t seem to distinguish between genuine happiness and the achievement of his dreams—he never considers what it would take to make himself, or anyone else, feel satisfied or fulfilled. Dexter’s struggle to reconcile his illusions to reality, therefore, is a result of his dreams preventing him from noticing and appreciating reality. No wonder he is so shocked and broken at the end of the story when he learns that Judy is in an unhappy marriage and that her beauty has faded—he has always expected the world to conform to his vision, and when he learns that this expectation has always been a fantasy, he realizes how little he has.
Dreams, Happiness, and Reality ThemeTracker
Dreams, Happiness, and Reality Quotes in Winter Dreams
Some of the caddies were poor as sin and lived in one-room houses with a neurasthenic cow in the front yard, but Dexter Green’s father owned the second best grocery-store in Black Bear—the best one was “The Hub,” patronized by the wealthy people from Sherry Island—and Dexter caddied only for pocket-money.
He became a golf champion and defeated T.A. Hedrick in a marvelous match played a hundred times over the fairways of his imagination, a match each detail of which he changed about untiringly—sometimes he won with almost laughable ease, sometimes he came up magnificently from behind. Again, stepping from a Pierce-Arrow automobile, like Mr. Mortimer Jones, he strolled frigidly into the lounge of the Sherry Island Golf Club—or perhaps, surrounded by an admiring crowd, he gave an exhibition of fancy diving from the spring-board of the club raft….
“I think I’ll quit.” 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. It is not so simple as that, either. As so frequently would be the case in the future, Dexter was unconsciously dictated to by his winter dreams.
Now, the quality and the seasonability of these winter dreams varied, but the stuff of them remained. They persuaded Dexter several years later to pass up a business course at the State university—his father, prospering now, would have paid his way—for the precarious advantage of attending an older and more famous university in the East, where he was bothered by his scanty funds…. 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. It is with one of those denials and not with his career as a whole that this story deals.
He did not consider it necessary to remark that he had once carried Mr. Hart’s bag over the same links, and that he knew every trap and gully with his eyes shut—but he found himself glancing at the four caddies who trailed them, trying to catch a gleam or gesture that would remind him of himself, that would lessen the gap which lay between his present and his past.
One minute he had the sense of being a trespasser—in the next he was impressed by the tremendous superiority he felt toward Mr. T.A. Hedrick, who was a bore and not even a good golfer anymore.
Next evening while he waited for her to come down-stairs, Dexter peopled the soft deep summer room and the sun-porch that opened from it with the men who had already loved Judy Jones. He knew the sort of men they were—the men who when he first went to college had entered from the great prep schools with graceful clothes and the deep tan of healthy summers. He had seen that, in one sense, he was better than these men. He was newer and stronger. Yet 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.
He could have gone out socially as much as he liked.... His confessed devotion to Judy Jones had rather solidified his position…. Already he was playing with the idea of going East to New York. He wanted to take Judy Jones with him. No disillusion as to the world in which she had grown up could cure his illusion as to her desirability.
He knew that Irene would be no more than a curtain spread behind him, a hand moving among gleaming tea-cups, a voice calling to children…fire and loveliness were gone, the magic of nights and the wonder of the varying hours and seasons…slender lips, down-turning, dropping to his lips and bearing him up into the heaven of eyes…. The thing was deep in him.
A sort of dullness settled down upon Dexter. For the first time in his life he felt like getting very drunk. He knew that he was laughing loudly at something Devlin had said, but he did not know what it was or why it was funny. When, in a few minutes, Devlin went he lay down on his lounge and looked out the window at the New York sky-line into which the sun was sinking in dull lovely shades of pink and gold.
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 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. And 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.
For the first time in years, there were tears streaming down his face. But they were for himself now…. The gates were closed, the sun was gone down, and there was no beauty but the gray beauty of steel that withstands all time. 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.