Describe Dexter's goals, what motivates him to reach these goals, and whether he succeeds in doing so.

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Dexter thinks of himself as a practical person whose ambition and hard work will enable him to achieve his goals. Deep inside, however, he is also a dreamer. Dexter sets reasonable goals such as success in business, largely out of desire to distance himself from his lower-middle-class, small town roots,...

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Dexter thinks of himself as a practical person whose ambition and hard work will enable him to achieve his goals. Deep inside, however, he is also a dreamer. Dexter sets reasonable goals such as success in business, largely out of desire to distance himself from his lower-middle-class, small town roots, but he does achieve these goals.

Dexter’s secret desires, however, are for glamorous, “glittering things" and people. He largely accepts these superficial things at their face value. Dexter is not particularly introspective. When he gets the chance to become Judy’s partner, albeit temporarily, he seizes that opportunity. In that case, he is more of a passive receiver of Judy’s favors, which is not a typical role for a go-getter like him. The dreamer part of him apparently wishes that the golden years of youth or summer could last forever. While his practical self knows that is a futile hope, his dreamer self weeps in recognition of winter’s having overtaken summer.

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The start of the story's second section addresses your questions best:

"But do not get the impression, because his winter dreams happened to be concerned at first with musings on the rich, that there was anything merely snobbish in the boy. He wanted not association with glittering things and glittering people--he wanted the glittering things themselves. Often he reached out for the best without knowing why he wanted it--and sometimes he ran up against the mysterious denials and prohibitions in which life indulges. It is with one of those denials and not with his career as a whole that this story deals."

 

Dexter wanted to be rich, and to possess everything that the rich get to have. This includes beautiful women, like Judy Jones.

 

Does he get everything he wants? No. He gets the wealth, and lots of it, but fails to gain true love.

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