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Having somewhat suddenly and rather dramaticaly ended his job working as a caddie at the golf course where he met Judy, Dexter clearly sets himself on a course to greatness. This is shown through his decision to go to an older and more respected university, which is also more expensive, rather than a newer, less prestigious (and therefore cheaper) university. What Dexter determines he will achieve in life is not simply the kind of lifestyle that is associated with the rich and famous, but the possession of wealth itself, as the following quote makes clear:
He wanted not association with glittering things and glittering people--he wanted the glittering things themselves.
How Judy embodies his "winter dreams" is that she, in the text, is described to be one of those "glittering things." Note the repeated reference to gold in her dress and appearance. It is clear that Fitzgerald presents her as being one of those objects of great wealth and desire that Dexter associates with success and the American dream, and with her breeding and attitude, she becomes the centre of his focus as Dexter seeks to be successful.
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