What is the symbolism behind the title "Winter Dreams"?

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The title "Winter Dreams" is symbolic of Dexter Green's future ambitions that are never realized, but which always occupy his mind.

Winter is a season when much of nature lies dormant. Likewise, in a sense, Dexter's dreams never really bloom and ripen; they always remain in a dormant state, or if they do germinate, the dreams do not live to fruition. 

Dexter's dreams lie dormant for some time after his initial encounter—the "strong emotional shock"—with the little rich girl, Judy Jones. So strongly is he taken with this "beautifully ugly" girl that Dexter dreams of nothing else but becoming wealthy so he can be on her economic level and earn her attention. He is "dictated to by his winter dreams."

Dexter achieves his dream of becoming rich, but his success is rather fortuitous. When he sees Judy nine years later, he is taken with her dazzling beauty, and the old dreams return. Again his heart is taken by another of her casual whims as she invites Dexter into her life, and he marries her after her rejection of a man she has just learned is poor. Thus, Dexter apprehends that Judy is "entertained only by the gratification of her own desires...." Nevertheless, his love for Judy is renewed. After a while, however, Dexter loses the dreams of grace and beauty, and Judy as well. Ironically, Judy, too, has lost.

F. Scott Fitzgerald uses the setting of the different seasons to convey Dexter's changing state of mind. The "winter dreams" symbolize his hopes of success, which vary and change. Often they are too brief and disappointing. Thus, the title "Winter Dreams" is symbolic of Dexter Green's future ambitions that are never realized, but which occupy his mind. Only the solid realities are left to Dexter. Just as each winter season varies from others, Dexter's "winter dreams" are at times shortened and insufficient, or they are prolonged with only brief moments of happiness.

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The use of the word "Winter" in the title of this F. Scott Fitzgerald story hides several meanings. There is the surface meaning: the main character has met the woman of his "dreams" in wintertime. Symbolically, winter is usually used to indicate aging and death. Throughout the story, the protagonist ages and the reader follows along with him through his journey. By the end, he has experienced a kind of "death": the death of his youthful idealism, his "winter dream". The woman that he was so enamored with has left him far behind, and he finds out that she is not the girl that he once knew: in fact, a part of her has died as well. Fitzgerald's title shows us that the dreams of the protagonist have withered with his age.

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What's the "winter dreams" that the title refers to?

"Winter dreams" are Dexter's fantasies of wealth and success, to which he frequently returns later in life, even after he attains the money and status that he craves. As Dexter grows older, his idealizations of the people for whom he caddied at the Sherry Island Golf Club become more lackluster when he gets to know them and discovers, for example, that T.A. Hedrick is not such a great golfer, after all. Though he does not yet know it, he is slowly reaching the realization that comes to him in the epiphany at the end of the novel: having money does not make one either happy or special.

It is true that, at the end of the novel, Dexter becomes disillusioned when he learns from his colleague Devlin that Judy, who has moved to Detroit and married a drunken never-do-well, has lost her beauty and, according to Devlin, may not have been so extraordinary looking to begin with. However, contrary to what the previous Educator writes, I do not think that the problem was ever with Judy to begin with. Though it is true that her affections for Dexter were fickle, his reasons for wanting to be with her have less to do with who she is and more to do with the status that Dexter believes he would have gained through a marriage to Judy Jones—daughter of the wealthy Mortimer Jones, one of the premier clients at the golf club.

The problem is that Dexter believed that after acquiring the "golden" things and becoming one of the "golden" people (Judy is frequently depicted in a golden light in the story), he would be happy. When he finds out that the girl who epitomized this ideal has fallen into a life of misery, his delusion, or "winter dream," of perfect happiness through materialism unravels.

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What's the "winter dreams" that the title refers to?

Winter refers to getting older, but it also refers to Dexter's feelings at the end of the story. He no longer cares or feels about anything when he realizes that Judy Jones isn't now or ever was worth having. Judy's beauty deteriorates over time, and Dexter realizes that his dream was just an illusion because Judy was shallow and spoiled. She was incapable of a real commitment. He wanted to be like the men at the golf club where he caddied, and he wanted to be good enough to marry Judy Jones. Dexter achieves material success, but he realizes money doesn't satisfy him. Only Judy Jones can make his dream come true.

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