The story develops around a man called Dexter Green, son of the owner of the second best grocery store in Black Bear. Dexter is a boy that comes from an upper class family, yet still knows the importance of working for riches and is fully prepared to do so. He is a caddie to the more wealthy men who meet at the club to play gulf Dexter at his 14 years old is typical good mannered young boy who dreams of one day being wealthy enough to have his own caddie. He is a hard working boy, that is known and respected as one of the top caddies of the golf course in Black Bear.
One day he meets Judy Jones, a wealthy , beautiful girl who all the men feel attracted to her at the club where he worked. He felt very attracted to her and soon realized that if he caddied for the young girl, he will never be able to have her because of his "inferior" conditions. That's how Judy becomes an embodiment of Dexter's illusions and dreams of entering into a higher social status, a world full of glamour and brightness. Caddying would show his lower social standing and therefore in her mind he would not have a chance.
He chooses to quit his job rather than caddy, but this was not only because of Judy but for his own dreams of becoming successful his "winter dreams" . Later after meeting, both had their first moment alone together and for Dexter it is something out of a fairy tale. "There was a fish jumping and a star shining and the lights around the lake were gleaming" Time stands still for him as he is with her, everything is perfect as the description of the lake and surroundings suggest. But what a surprise is to find out that Judy only wants him to drive the motor boat so she can go surfboarding.
At the beginning of the story it was Dexter's social status that kept him from Judy, but as the story continues yet he has become a successful business
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