Dexter's dream that begins, then flourishes, but becomes unattainable in the end, exemplifies F. Scott Fitzgerald's corrupt idea of the typical American Dream. Society as a whole believes the American Dream consists of the freedom of individuality, material wealth, better landscape, and religious idealism. They look for the idealistic concept of what they want it to convey, rather than what it actually is. "Winter Dreams- portrays different thoughts of Fitzgerald's, particularly from events that happened in his own life during the Jazz Age.
The beginning of Dexter Green's dream happens around 1911 at a golf course in Minnesota that he caddied for at the age of fourteen. A young girl of eleven, "beautifully ugly as little girls are apt to be,"" arrives to golf with her nanny when Dexter is instantly charmed by the girl's beauty. For Dexter, the girl appears "to be inexpressibly lovely- and will "bring no end of misery to a great number of men- (590). However, this girl uses her status to boss Dexter around. Instead of acting as nothing more than a caddie for the girl, Dexter quits his job. He can now direct his attention towards her and nothing else.
As the years pass by, Dexter's dream becomes a reality. As a recent graduate from college, Dexter now runs his own laundry business. He receives an invitation to the golf course that he worked for so many years before. At this point, Judy, the girl from Dexter's teenage years, has blossomed into a lovely young woman. By accident, these two cross paths while on the golf course. When Dexter inadvertently asks her to dinner, it marks the beginning of their relationship. However, Judy is never content with one man. She enjoys the company of many others. Jealousy comes upon Dexter, but then it became old after a while. He cannot accept Judy's lack of commitment. Time moves on and Dexter and Judy only come in contact a few times. Dexter longs for her and knows he will never find satisfaction without her.
