Take a look at this passage, from Section 3, when Dexter finally nabs a date with Judy:
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. (3.7)
The reason for Judy's sadness matters less than Dexter's response to it (though it does tell us something about her character). He can see that something is wrong. But Dexter cannot for the life of him figure out what it is. The problem is, Dexter can look at Judy all day long. He just doesn't understand her. That, in and of itself, is pretty darn sad. He longs for a Judy he'll never have.
The language of the passage makes us feel like we don't actually know what's going on ("uneasiness," "worried," "disturbed"). Fitzgerald's use of all of these anxious words makes us anxious as readers. And we'd bet that was intentional. The tone in this passage helps reinforce the idea that Judy is to be longed for, but never to be had. She's a dream, but she is also an unreachable goal.
How about one more example, with an equally wistful tone:
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. (6.34)
What's going on here? Check out the repeated words of loss: "gone," "taken," "no longer." The narrator practically beats us over the head with it: Dexter has lost something – his dream, to be precise. And when he realizes this, he longs for what he's lost downright desperately. All he has now are memories, of a woman he never really had, and of dreams he never really achieved.
Dexter Green starts "Winter Dreams" at age fourteen and ends it at thirty-two, so he clearly comes of age over the course of the story. But Dexter's coming-of-age is not a positive triumph over his obstacles. He has to face the bitterness of losing his ideals and compromising his dreams.
The story's interest in Dexter's psychology (rather than in some exciting plot line with lots of twists and turns) indicates that "Winter Dreams" is an example of literary fiction. Fitzgerald's careful style and melancholy tone are formal storytelling elements that belong to literary fiction rather than to, say, the superhero story or the detective novel. (Dex would probably make a really lousy superhero anyway.)
You know the saying that in spring, "a young man's fancy lightly turns to thoughts of love"? Well, this is a story about a young man and his thoughts of love, but as the title tells us, it is certainly not set in spring.
All of Dexter's fantasies about a brighter future come to him during the bitter Minnesota winter instead of the spring and summer, when the poets tell us we are supposed to daydream. Basically, Fitzgerald is slapping us across the face and telling us that he's doing it differently. So take that. This is a new kind of story about dreams, different from the classic poetic associations between dreaming and spring.
For more on the symbolism of the title "Winter Dreams," check out our section on "Symbols, Imagery, Allegory."
Throughout "Winter Dreams," we are under the impression that this is the story of Dexter Green's love for Judy Jones. But at the end of the story, once Dexter finds out that Judy has lost her charms and settled into a bad marriage, we begin to wonder if this story is about something else entirely. Dexter does not weep for Judy. He weeps for himself, for the young man he once was and for the illusions he once held. Deep stuff.
Dexter thinks, "Long ago […] long ago, there was something in me, but now that thing is gone" (6.36). We can't be totally sure what Dexter means by "that thing," but we'll take a stab at it. Dexter falls in love with Judy the same day that he quits the Sherry Island Golf Club. It's at that moment that he decides he is going to be one of the rich and famous men who go to golf courses, and not the kid who helps them.
Our guy associates Judy with that dream of a rich and fabulous future. So once she loses her looks and falls into a marriage with a cheating alcoholic, Dexter loses the last of his illusions about the romantic life of the upper class.
And as for Dexter, he realizes that his pursuit of those dreams at all costs have left him with a big fat nothing. He has given up the idealistic feelings of his youth in favor of his hard-minded business sense. And now he can't recapture "the richness of life" (6.35) that he appreciated as a younger man. Not a very uplifting ending, to say the least.
Most of the action in "Winter Dreams" takes place at the Sherry Island Golf Club. It's there that young Dexter first sees even younger Judy Jones; it's there that Dexter falls for Judy Jones a second time as an adult; it's there that Dexter sees the lifestyles of the rich and famous, which he wants for himself. Who knew country clubs were the center of so much action?
Sherry Island is actually the perfect place for this story. First, the natural loveliness of Sherry Island ties the ideas of beauty and money together in young Dexter's mind: where there's beauty, there's dough (true enough of Judy Jones!).
Second, Sherry Island allows us to imagine the class issues of the story geographically. In other words, Dexter is from Black Bear Village. We are sure that Black Bear Village is a very nice place, but it gets essentially no description from the narrator. It is a place of no importance in Dexter's imagination. On the other hand, Sherry Island – where all the rich people live – makes Dexter feel "magnificently attune to life […] radiating a brightness and a glamour he might never know again" (2.28). Sherry Island is the place where Dexter goes when he is dreaming of improving his social and financial standing.
The fact that Sherry Island is close to the place Dexter grows up reminds us of Dexter's own class background: he is middle class, but his origins are humble. He wants to spend all of his time at Sherry Island, but he can never forget that he comes from somewhere else. He does not (yet) belong in the rich world that Sherry Island symbolizes for Dexter.
The comparison between Sherry Island and Black Bear Village is similar to the comparison between New York and Minnesota. In other words, like Sherry Island, New York City (and specifically, Wall Street) represents this space of richness in comparison to Minnesota. Dexter starts off in Minnesota, but just as he left Black Bear Village, he moves on to bigger and better things. As a Minnesota native himself, Fitzgerald is highly aware of the social differences between St. Paul and New York. For more on this topic, check out our "Symbols, Imagery, Allegory" section.
F. Scott Fitzgerald writes clearly, with lots of cool images to make it easier to imagine the people and places he describes. But even if Fitzgerald's word choice often seems simple, he likes to use symbols and metaphors, so there's still some careful reading to do.
"Winter Dreams" switches back and forth between beautiful imagery and relatively straightforward dialogue and description. For every brisk exchange we get between Dexter and his business associates, we also get a passage like this one, as Dexter goes for a nighttime swim off Sherry Island:
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 attune to life and that everything about him was radiating a brightness and a glamour he might never know again. (2.28)
There sure is a lot of style packed into that short passage. First of all, we have this strong sense of time passing. As Dexter listens to the music, he thinks of a prom five years ago, when he had to stand outside the gymnasium to listen to the activity inside. (Sad night, eh?) In other words, Dexter looks back to a time when he was just on the edge, both physically and symbolically, of financial success. He was just outside his college's social sphere. Now Dexter is participating actively in the social lives of the local rich. He has even played golf with – oh yes – T.A. Hedrick. The music that he hears reminds Dexter of where he was five years ago and of far he has come today. We can see how the style very nicely contributes to the wistful, nostalgic "Tone."
This passage also reminds us that Dexter associates wealth and social success with artistic appreciation and with beauty. Basically, whenever he's around rich people, he thinks life is beautiful. Superficial much? As Dexter listens to the music and sits in the darkness, he feels "magnificently attune to life." Everything on Sherry Island seems to be "radiating a brightness and a glamour he might never know again." The rich language of this passage, which emphasizes "ecstasy" and "brightness" and "glamour," easily shows us the beauty that Dexter associates with the rich life. These wordy, descriptive passages give us some taste of the artistry that Dexter wants out of his fantasies of wealth. He really has high hopes for what living the high life will feel like.
Moments like this contrast strongly with the ordinary conversations that Dexter has with his golfing partners or with Devlin. All of Dexter's romantic idealism comes from his own imagination, and all of the actual scenes of rich people interacting are strikingly dull. They lack the lushness of these descriptive moments in "Winter Dreams." Fitzgerald uses these contrasting rich and straightforward writing styles to emphasize the difference between Dexter's dreams of high society and the humdrum reality of the business world that he wants to enter. It's not all it's cracked up to be.
The Sherry Island Golf Course is probably the most obvious symbol in "Winter Dreams." When we think about golf, we think about money. Belonging to a country club is a long-standing sign of privilege in American society.
Dexter goes to the golf course to earn some extra cash as a caddy, but he doesn't really need that extra dough. What he really wants from the Sherry Island Golf Club is a chance to watch the daily habits of the rich and successful. Dexter's job at the golf course provides material for his winter dreams.
At the beginning of "Winter Dreams," the Sherry Island Golf Club represents everything that Dexter wants to achieve. The golf course – and Dexter's eagerness to be on it – symbolizes wealth and high status. By the second section of "Winter Dreams," the golf course has become a transitional space where newly-rich Dexter tries to remember what it was like to be a boy caddying there. What happens once Dexter finally has the chance to golf on the course? Is it everything he'd hoped and dreamed?
During the cold Minnesota winters (and we mean cold – trust us), when the golf course is frozen over and Dexter can't interact with the upper class people he envies, all he has left are his winter dreams. These dreams are the metaphor that Fitzgerald uses to refer to Dexter's ambitions for the future. In section one of "Winter Dreams," Fitzgerald writes:
October filled him with hope which November raised to a sort of ecstatic triumph, and in this mood the fleeting brilliant impressions of the summer at Sherry Island were ready grist to his mill. He became a golf champion and defeated Mr. T. A. Hedrick in a marvellous 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. (1.4)
Dexter's specific dream in this case is to play golf with Mr. T.A. Hedrick and win. Beating a rich dude at golf is his big dream? Well, yeah, but it's more about what it would mean: if he could do it, Dexter would have really, truly joined that wealthy world he only observes from a distance as a caddy.
And remember, these dreams become more and more "ecstatic" as the winter continues. As the winter gets colder, Dexter gets more excited about what the "brilliant impressions" that summer will bring. The fact that Dexter's imagination only runs wild when he is not actually hanging out with the people he caddies for in summer is a pretty good hint that his romantic ideals about the rich life are not based in reality. Being rich isn't all that grand, it seems.
Dexter's winter dreams are fantasies. They have no real grounding in truth – much as Judy Jones' beauty does not necessarily reflect her character underneath the surface. The final proof of this contrast between Dexter's winter dreams and reality comes at the end of the story, when Dexter appears to have achieved everything he has ever wanted. But he has lost those dreams of grace and beauty that he used to have as a boy in Minnesota.
In a lot of ways, Fitzgerald uses "Winter Dreams" to comment on the American myth of the self-made man. He's basically saying, yes, it is possible for an American to come from nowhere and make tons of money; but don't expect perfection. This self-made man may find it disappointing (and soul-destroying) once he's reached his goals.
But here's the thing: Fitzgerald also doesn't present the United States as a giant, unified block. There is some major regional difference in this story. The East Coast represents old money and high finance, while the Midwest (or "Middle West") represents energy and ambition. Do you think Fitzgerald is making a judgment call here? Is one better than the other?
Dexter comes from Minnesota, but in order to feel like he is really gaining social status, he has to go to college at an elite institution back East. Even though Dexter makes it big as a businessman in the cities of Minnesota, he has not really proven himself financially until he can take his cash to Wall Street, in New York. But Dexter's origins outside of the East Coast are also what make him "the rough, strong stuff from which [the upper class in the United States] eternally sprung" (3.1).
Once Dexter gets to Wall Street, his business associate Devlin comments, "So you're from the Middle West […] That's funny – I thought men like you were probably born and raised on Wall Street" (6.3). Now that Dexter has succeeded in New York, it's like his origins in the Midwest (where he dreamed his winter dreams) have faded away. So Fitzgerald is drawing a comparison between Dexter's boyhood dreams and Minnesota. With his success, Dexter has, in a sense, lost both of them. The closer he has grown to that American center of finance, Wall Street, the further away he has traveled from the ideals of the boy he once was. Wait, we thought Los Angeles was the city of lost dreams...
The narrator of "Winter Dreams" talks about Dexter Green in the third person, so we know we're looking at a third-person narration here. But here's the kicker: the narrator focuses all of his descriptions of thoughts, impressions, and memories on Dexter. Even if this is not a first-person story told from Dexter's point of view, it often feels as though Dexter is the only realistic, three-dimensional character in "Winter Dreams." This is why we call it a limited omniscient narrator: he knows everything there is to know, but his knowledge is limited to one person, Dexter Green. All the other characters, even Judy Jones, mainly appear to flesh out Dexter's own character.
At the start of "Winter Dreams," Dexter Green is a fourteen-year-old Minnesotan kid. He spends every winter waiting for the sun to melt the snow on the Sherry Island Golf Course so that he can caddy for the summer. Dexter has a natural attraction to the world of the wealthy. We know that he is better at mingling with the upper class than the other caddies because, when he quits his caddying job, Mr. Mortimer Jones says that Dexter is "The best — caddy I ever saw" (1.10).
The main conflict of "Winter Dreams" is that Dexter dreams of joining the ranks of the rich. But when he sees Judy Jones – the lovely daughter of one of Sherry Island Golf Club's members – on the golf course, he realizes that he has been going about it all wrong. He cannot become rich by earning extra pocket money here and there. He decides to remake himself entirely, so that he will be worthy of someone as lovely as Judy. Once Dexter sees Judy for the first time, his "winter dreams" of fame and fortune become definite ambitions that he will give anything to achieve.
Dexter Green has been busy remaking himself. It's been nine years since he quit his job at the golf course, he has gone to college on the East Coast, and he has come back to Minnesota to make some smart investments in the laundry business. Dexter is already an up-and-coming rich guy. He now plays golf with the men he used to caddy for back in the day. Just as it seems as though all of Dexter's dreams are coming true, Judy Jones comes back into his life. He meets Judy on a swimming platform in the middle of Black Bear Lake, near the Sherry Island Golf Club. Dexter realizes that he has always wanted Judy – but Judy doesn't want Dexter back in the same way. So even though Dexter's business life is running smoothly, his romantic dream of Judy Jones remains out of his reach.
We know that the introduction of Irene Scheerer into Dexter's life probably isn't going to alter Dexter's feelings for Judy. After all, the adjectives that Fitzgerald uses to describe Irene – "sturdily popular" (4.18) and "solid" (4.18) – are not the stuff of romance. We are just waiting for Judy to come back on the scene. And indeed, before we know it, Judy reappears and Dexter's on-again-off-again affair with her starts up once more.
We know that Dexter's relationship with Judy is doomed to failure (since she just is not that into him). How is this going to jive with the big dreams he has? What will happen next?
Failing in both his relationships with steady Irene and fickle Judy, Dexter gives up on women all together. He registers for the Army when the U.S. joins World War I in 1917. And then he moves to New York to make even more money. Dexter dedicates himself to becoming as rich as he possibly can – and he leaves behind his romantic illusions of Judy Jones for good.
By the end of the story, Dexter has apparently achieved all of his goals: he is rich and successful. In fact, he is so well off that "there were no barriers too high for him" (6.2) to overcome. At this point, Dexter has not been back to the Midwest for seven years. Those years pining after Judy Jones are long past. But it is not until his business associate, Devlin, mentions in passing that he knows an unhappily married woman named Judy Simms (maiden name Jones) that Dexter realizes how far he has come from the romantic boy he was in Black Bear, Minnesota. In his pursuit of money, Dexter has forgotten the ideals of romance and grace that led him to try to become wealthy in the first place. He has grown hard-minded and unemotional. Not even the news that Judy has ruined her life with a bad marriage can truly move him. Dexter weeps when he realizes there is nothing left of the boy he once was. Weirdly, Dexter's success has killed off his winter dreams.