What are Dexter's responses when Judy keeps appearing in his life in Winter Dreams?

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When Dexter Green first sees Judy Jones, she is only eleven; however, he is struck by the beauty of this girl and "winter dreams" of attainable beauty and of being rich begin to dictate his life. For the first time, Dexter begins to "reach out for the best without knowing why"; he wants "the glittering things." Much like Jay Gatsby of Fitzgerald's novel, Dexter believes that if he attains those "glittering things," he can then have whatever he wants. 

After Dexter becomes wealthy from owning a large chain of laundries, he goes to the Sherry Island Golf Club and plays with some pretentious men. When one of the men loses his ball in the rough, "an enormous thing" happens to Dexter:  he encounters again the beautiful Judy Jones, who "plays through" her golf ball that has come flying past them. Later that day, Judy passes by him in a motor-boat; she invites Dexter to drive it so that she can ride her surfboard behind, and "for the second time, her casual whim gave a new direction to his life."

The next evening Dexter has a dinner date with Judy at her home. After dinner they sit alone on the sun-porch because her parents are gone. Judy explains her "moody depression" during the meal as caused by a man's revelation to her of his poverty when she had not suspected it, and it only shocked her because he had concealed it. As the evening continues, she kisses Dexter and he decides "that he had wanted Judy Jones ever since he was a proud, desirous little boy."

Further, Dexter "surrendered a part of himself to the most direct and unprincipled personality" he has ever encountered; he becomes one of many who receive attention from this beauty. As a result, Dexter becomes frustrated and dissatisfied. When he asks her to marry him, she replies emptily about someday,yet Dexter continues to find her desirable. After a while, he realizes that Judy has become indifferent to him, so he becomes interested in Irene Scheerer as a substitute for his loss, and eventually he proposes to her.

One night when Irene has a headache that puts her to bed, Dexter stands casually in a doorway at the University Club and Judy appears as part of a warm breeze that blows through the room; Dexter "could have wept at the wonder of her return" because everything that was mysterious had left with her; Judy is yet associated with all Dexter's "winter dreams." As they talk, Judy confuses Dexter by saying, "I wish you'd marry me" even though she knows of Irene. Overcome with emotion that his "beautiful, his pride" has returned, Dexter again surrenders to the dreamlike hold Judy has upon him, and he enters her house when she invites him after driving her home.But, Dexter cannot keep her and Judy terminates their engagement. So, he enters the war with a sense of relief, "welcoming the liberation from webs of tangled emotions."

Seven years pass and Dexter has relocated in New York. One day a man named Devlin comes to the office on business; coincidentally, this man's best friend has married Judy Jones. Devlin tells Dexter that Judy was once very beautiful but having a husband who acts "outrageously" has had an affect upon her. As Devlin describes the mundaneness of Judy's life now, Dexter becomes aware that a "sort of dullness settled down" upon him. "The dream was gone." An animation is taken from Dexter and he can never return to it; Dexter cries at the loss, knowing that he "could never go back any more" to his youthful illusions:

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.

An emptiness strikes at the core of Dexter as that idealization of beauty and love is now gone.

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Winter Dreams

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