How do Dexter's views on the American dream change throughout "Winter Dreams"?

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In the beginning of "Winter Dreams" by F. Scott Fitzgerald, Dexter's view of the American dream is to become rich and famous. By the end of the story, however, his view of the American dream has become caught up in his desire to win Judy Jones.

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At the beginning of the short story "Winter Dreams" by F. Scott Fitzgerald, Dexter's views about the American dream are connected with ideals of fame and fortune. When he is still a caddy, he envisions himself as a wealthy and admired man who owns an expensive car and earns admiration by winning golf games and performing fancy dives off the springboard of the club raft.

Eventually he borrows money, starts a laundry business, and becomes rich. He is able to visit golf clubs as a player instead of a caddy in the company of wealthy men whose golf equipment he used to carry. This is Dexter's first vision of the American dream, but it all changes when he meets Judy Jones as an adult. He drives her boat while she uses the surf-board, and then she invites him to dinner. Fitzgerald writes that "her casual whim gave a new direction to his life."

After that meeting with Judy Jones, the American dream for Dexter is no longer fame and fortune. Instead, it is to win Judy. She has many boyfriends and has received proposals multiple times. She meets and discards boyfriends casually, without any regard for the hurt she might be causing them. Still, for Dexter she is the embodiment of the American dream: a beautiful, wealthy, privileged woman who can take her pick from among the men who court her.

Dexter and Judy have an off-and-on affair. He is aware that she is seeing other men at the same time. He asks her to marry him, but shortly after that, she becomes involved with someone else. Dexter's engagement to Irene Scheerer is in the nature of a compromise. He has not forgotten about Judy. Realizing he can most likely never win her, he opts for Irene as a source of reasonable happiness and stability. However, when Judy reappears and proposes to Dexter, he instantly cancels the engagement and goes back to Judy. It still doesn't work out, but Dexter does not regret the interlude. He realizes that "he loved her, and he would love her until the day he was too old for loving."

We see then, that at first Dexter's view of the American dream is acquiring fame and fortune, but later it becomes the winning of Judy Jones.

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Though it is true that Dexter does not merely want proximity to the "glittering people and the glittering things" but wants to be one of those people and own those things, his standards are derived from those whom he believes are his betters.

While caddying at the club, he fantasizes about beating T.A. Hedrick, one of the members of the Sherry Island Golf Club, in "a marvelous match played a hundred times over the fairways of his imagination" and giving "an exhibition of fancy diving from the spring board of the club raft" before an "admiring crowd." He also envisions himself "stepping from a Pierce-Arrow automobile, like Mr. Mortimer Jones," perhaps the wealthiest inhabitant of Black Bear, Minnesota, and the father of Judy Jones, whom Dexter claims to love. It is arguable that Dexter's love of Judy is at least partly influenced by his desire to fit in among the wealthier members of town. When he visits her home, he imagines "the men who had already loved Judy Jones," men who had gone to "great prep schools." He knows that, as the child of an immigrant, he is "newer and stronger," but "he wishes his children to be like them"—established and at ease in their status.

Dexter's desire to be among particular members of high society does not stop in Black Bear; he decides to forgo a business program at the state university to attend a "more famous university in the East, where he was bothered by his scanty funds." Despite his father's prosperity as a grocer, he could not stop measuring himself against those who had more. This is one of Dexter's pitfalls—his inability to be satisfied with any of his accomplishments because the idea is that one can always have something more or better. He abandons his plans to marry Irene Scheerer, a nice and attractive young woman from a prosperous family, because he believes that Judy Jones is better. This tendency is one of the pitfalls of the American Dream and one that Fitzgerald illustrates more eloquently at the end of The Great Gatsby: a tendency to strive constantly toward something indefinable but always on the horizon.

I would also say that Dexter's dream does not change, and that this is the root of his problem—his inability to evolve or adapt. It devastates him when his associate, Devlin, tells him about Judy's aging and her unhappiness. This is not because he feels particularly bad for her, but because his idea of her and of what he could be with her at his side (prominence and official membership in the upper class) evaporates. In other words, his view does not change, but the world around him does. Therefore, at the end of the story, he realizes that he can never go back to the golf club; he cannot repeat the cycle he established earlier in the story by going back home, resuming his relationship with Judy, and then setting back off into the world as though nothing would change.

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When Dexter is a young man, his "winter dreams" about success are not about social climbing. He determines that he is not interested in becoming a member of the club in which he caddied as a boy. In his mind he decides: "he wanted not association with glittering things and glittering people—he wanted the glittering things themselves." Dexter's first iteration of the American dream is materialistic. He wants, literally, to acquire, not just be near, the finer things in life.

By the end of the story, Dexter is utterly disillusioned. He has achieved success in business and acquired all that he had desired. The news of Judy Jones's diminished beauty and desirability is the catalyst that leads him to conclude that all of the markers of achieving the American dream are ultimately meaningless. The superficiality of how Dexter had defined the American dream deflates him and lead him to sadly observe that

Long ago . . . 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.

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How do Dexter's views about the American dream change from beginning to the end of the story "Winter Dreams"?

Dexter is shown progressing from adolescence to middle age. The character of Judy tantalizes him at every stage but in a different way at each stage of his life. His version of the American dream is caught up in his obsession with this unattainable girl. Although Dexter achieves professional success and becomes a very wealthy businessman, he largely takes those achievements for granted. He cannot be honest with himself and admit that the things he has gained really have no value and his unease arises from having wasted his life. Instead, he attaches his dissatisfaction to the inability to possess the woman of his dreams. Those dreams are ultimately revealed to be cold and unappealing, as Dexter finally realizes that even Judy is ordinary and ages like everyone else.

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