In "Winter Dreams," how does Dexter Green come to realize the "American Dream" is an illusion?

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Susan Hurn | College Teacher | (Level 1) Educator Emeritus

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From the time he is a poor boy caddying for rich people at the Sherry Island Country Club, Dexter's version of the American Dream is to live a life of  beauty and glamour that he believes he can achieve through money. He wants to be wealthy--to escape his ordinary life and the social class into which he was born. These are his romantic winter dreams.

Dexter works hard to achieve his dream. He scrimps to attend a college more expensive than he can really afford. He graduates, starts a business, expands it, and then sells out, making a lot of money. He is wealthy. Along the way, he has learned to speak and act and dress like members of the upper class. Dexter has money, but he does not have beauty and glamour in his life until he meets Judy Jones, whom he had known when she was a child.

After one gorgeous evening on the lake, Judy becomes Dexter's dream, all the beauty and glamour he has hungered for since he was a boy. His affair with Judy does not last long because her love was an illusion. Despite his pain, Dexter does not regret having loved her. He carries his memories of Judy with him always, still cherishing her beauty and reliving their affair. His memories are all that he has left of her. He lives for them.

The story ends when Dexter learns that Judy is no longer beautiful. She is unremarkably ordinary. His memories of her dissolve as he tries desperately to keep them. Her love had been an illusion. His memories have been lies. He is left with nothing.