What motivates Dexter to fall in love with Judy in "Winter Dreams"?

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Much like F. Scott Fitzgerald himself, Dexter maintains the perception of the rich as possessing some magical quality; thus, he is easily motivated to fall in love with Judy in order to experience such magic.

When he first sees Judy at age fourteen, she is a younger girl, and he notices the "passionate quality of her eyes." Her smile, too. arrests him: it is "radiant, blatantly, artificial--convincing." Later on, Dexter describes this smile to himself as "preposterous." In a way Judy is Dexter's muse; that is, she inspires Dexter to become rich so that he can have a chance with her.

However, because Dexter's vision of Judy is unrealistic, serving only to inspire his own fantasies, his "winter dreams" become illusory and fated as he is "unconsciously dictated to by his winter dreams." While he does attain wealth, the magical quality is lacking, and Dexter is disappointed in his renewed relationship to Judy after he abandons Irene. For, she is

...entertained only by the gratification of her desires and by the direct exercise of her own charm.

Yet, tenaciously Dexter holds his dreams of Judy, and it is only when he learns years later of Judy's loss of beauty and her mistreatment by her husband, that Dexter sadly realizes that she, too, is made of clay. "The dream was gone. Something had been taken from him" when Dexter hears of Judy's mundane life that lacks any animation. Dexter has lost his "winter dreams."

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In "Winter Dreams," what motivates Judy to behave as she does in her relationships with Dexter and others before she is married?

It's fair to say that Judy's a bit of a spoiled brat. She comes from an elite, privileged background where everything's been served up to her on a silver platter since she was knee-high to a grasshopper. What Judy wants, Judy gets, and that extends to the men in her life. She likes to be in control, and toying with men's affections is a great way to do that. Judy's wealth and privilege allow her to play the field before she gets married in a way that would not have been thought acceptable for women at that time. In effect, Judy's taking on the role traditionally associated with men. This is reflected in her penchant for golf, which then and now was a predominantly male-dominated activity.

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In "Winter Dreams," what motivates Judy to behave as she does in her relationships with Dexter and others before she is married?

Judy may be beautiful and rich, she is also cold-hearted and shallow. She loves to toy with the affections of both Dexter and the other men who fall for her. She is only interested in a particular male for a short time. Her motivation seems to be an unhealthy need to be the center of attention and to fill a void in her life. She has always had everything she needed, and has never been challenged enough to have to fight for what she wants. This has left her without feelings for others and a belief that her beauty is enough for any man. As she says,‘‘I'm more beautiful than anybody else … why can't I be happy?’’ But beauty is fleeting and, one would think, Judy is in for a rude awakening some day.

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