What action does Dexter take after his first meeting with Judy Jones and what happens during their second meeting?

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Early in the story, after Dexter's winter daydream of becoming golf champion, he decides to stop caddying because he is too old. Fitzgerald implies that Judy Jones is at least part of the cause of his quitting with the paragraph beginning, "The little girl who had done this was eleven--beautifully ugly as little girls are apt to be who are destined after a few years to be inexpressibly lovely and bring no end of misery to a great number of men." 

Dexter is fourteen and this is his first encounter with Judy. Although Judy was so young, he foresaw that she would be very beautiful in later years. When the caddy-master demands that Dexter pick up Judy's clubs and caddy for her, he definitively quits because such a gesture (possibly in defiance of the adults and an alliance with Judy) felt necessary after his encounter with Judy. That is to say that Dexter felt he needed to quit because of the "strong emotional shock" he'd just experienced. 

Nine years later, (Part II) while golfing with Mr. T. A. Hedrick, Mr. Sandwood, and Mr. Hart, Judy hits a ball behind them that strikes Mr. Hedrick in the abdomen. Later that afternoon, Dexter sees Judy while he is swimming. She asks him to drive her boat so she can ride behind on a surf board. He complies. She asks him to dinner and he accepts. Dexter soon realizes that he must compete for Judy's attention with other men. He finds himself in a position of being Judy's shoulder to cry on as well as a potential mate. Having all these men to choose from, Judy alternately encourages and discourages Dexter. He eventually finds another girl: Irene. (However, this would not be the end of his infatuation with Judy.) 

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What actions does Dexter take as a result of his first two meetings with Judy in "Winter Dreams"?

Through meeting Judy Jones, Dexter has gained a brief insight into how the rich and privileged behave. There's something remarkable about Judy's impetuosity, which to the untrained eye would look like a spoiled brat throwing a tantrum, but which to Dexter seems like an admirable display of real passion. Not only is Dexter hopelessly smitten by Judy, he's also now resolved to live his life by the same rules; he wants to do his own thing.

His sudden resignation from his caddying duties is a way of showing solidarity with Judy. More than that, it's the only way he knows how of expressing the intense emotions that this spoiled little rich kid have unaccountably inspired in him. In any case, Dexter now feels, like Judy, that he's a damn sight better than those around him, and that he must follow his own path in life. The downside of this resolution is that, unlike Judy, Dexter will have to work hard to get where he wants to be.

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What actions does Dexter take as a result of his first two meetings with Judy in "Winter Dreams"?

Dexter's first meetings with Judy Jones are the impetus for his "Winter Dreams." A lowly caddy, Dexter meets the haughty little girl, all of eleven years old, on the golf course. Her derision of him makes him rethink his life. When Judy bangs up her clubs in a fit of temper, the caddy-master demands, "What are you standing there like a dummy for? Go pick up the young lady's clubs."

Instead of suffering her insults, Dexter impetuously declares:

"I think I'll quit.

The enormity of the decision frightened him. He was a favorite caddy and what he earned through the summer was not to be made elsewhere in Dillard. But he had received a strong emotional shock and his perturbation required an violent and immediate outlet.

Dexter works hard to prove to Judy Jones that he is one of the elite, if not by birth, and her equal. By the end of the story though, Dexter realizes how hollow, like a dry twig in winter, that his lifelong dream, has been.

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What action does Dexter take as a result of his first meeting with Judy Jones?

An argument can be made that Dexter recognizes what he covets when he first sees Judy.  In many ways, Dexter only fully recognizes what he wants out of his own life when he sees Judy and what she represents.  Her sense of style or panache, and the manner with which she carries herself without fear, without any hesitance, and, most importantly, with much in way of money helps to animate Dexter's own vision of coveting wealth and wanting to belong to a social setting where its trappings are dominant.  Dexter is not repulsed when he sees Judy. Rather, he is taken with her and her representation of a world of wealth and privilege that he is not able to partake at the time, but one to which he certainly seeks to belong upon seeing her.

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