1. Often he reached out for the best without knowing why he did 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.
This quotation, from part II, underscores the ways in which denial informs the story, as the wealthy characters in “Winter Dreams” are forced to confront the fact that the complexities of happiness are difficult, even impossible, to master. Dexter’s life, as portrayed in the story, spans his mid-teens to early thirties and is marked by a flurry of business activity but little introspection. His winter dreams of money and comfort are as insubstantial as the snow he skis across as a young man, fantasizing about a life of ease and admiration. But Dexter never pauses to examine what motives and desires actually drive his actions. Because Dexter has not analyzed his instinctive grasping for “the best,” the news of Judy’s unhappy marriage and compromised beauty affect him all the more profoundly.
In this quotation, Fitzgerald sets up a dichotomy between the personal realm and public arena, where Dexter makes his most profound mark. Although Fitzgerald is attempting to isolate one aspect of Dexter’s varied life, he is also suggesting that the story’s preoccupation with the rich is merely a ruse, meant to expose the hollow core of a world that is often too obsessed with the material trappings of success. The denial Dexter faces reverberates on many levels, referring not only to Judy’s fickle affections but also to the more profound denial of happiness that emotionally cripples Dexter at the end. Finally, the quotation is noteworthy because it shows that Fitzgerald is assuming an analytical stance that his protagonist does not. Fitzgerald attempts to guide the reader to the wisdom and insight that he was hoping to convey. He acknowledges that his story is exactly that—a story—and that it serves as a cautionary tale for readers.
2. “Who are you, anyhow?”
“I’m nobody,” he announced. “My career is largely a matter of futures.”
This exchange between Judy and Dexter takes place at the end of part III, when the couple is talking on the sun porch. The exchange is seemingly innocuous, but Dexter’s answer reveals his essential failing and the personal obstacle he is never able to overcome as he searches for identity and meaning. As an individual, shorn of class distinction or the mark of worldly success, Dexter has a limited grasp of who he is. His winter dreams primarily concern rising above his station in life, ignoring the intangible aspects of happiness and personal development, which flounder in his drive for wealth. Dexter is a “nobody” who turns to the professional world and his own success for self-definition. However, when it comes to establishing his presence as a fully realized individual, Dexter lingers on the edge of himself, as when he hovers in the shadows of a party held at the club where he lives, watching the dancing couples. He is unable to penetrate the heart of not only this world of frivolity but of himself as well.
Happiness with Judy and then Irene eludes Dexter as he looks to these objects of his desire to define him. Judy in particular is a disastrous choice, a female complement to his persona of a lost wanderer unable to firmly root himself in his life. Judy’s question reveals her often shallow way of relating to those around her. While the question smacks of abstract concerns of identity, Judy is simply slyly asking Dexter whether he is of adequate financial means. Her follow-up question of “Are you poor?” shows the true nature of her inquiry and reveals the extent to which she is interested only in a man who can provide her with material goods. If her partner is devoid of personal character, a state Dexter dangerously flirts with, she doesn’t much care.