In "Winter Dreams," how do Dexter's "winter dreams" reflect discontent? Does this discontent subside when he becomes rich and respected?
From the time he was a boy, Dexter was restless and discontented, reaching for a larger life than the working middle-class life into which he was born. He longed for a life of romance, beauty, and glamour; he wanted wealth and the "glittering" lifestyle money could buy. When he was young, Dexter escaped his limited personal circumstances through his dreams, imagining scenarios in which he was the star, the hero--one who was admired by the same wealthy people he encountered while working summers at the private and elite Sherry Island Golf Club. Dexter grew up as an outsider who longed to be an insider.
After scrimping to attend one of the "top" Eastern universities, Dexter built a fortune for himself through hard work and ingenuity. He returned to Sherry Island as a guest, not an employee. He had arrived, but in a substantial way, Dexter was still the outsider, and he was still enchanted by Judy Jones and the glamorous world she represented for him. He fell into a love affair with her, one that ended very painfully for him.
Going on with his life, Dexter became engaged to Irene, a fine young woman, but one who could not begin to compete with his memories of Judy. When Judy came into Dexter's life again, he dropped Irene instantly to pursue Judy anew, again with painful results.
Even as a wealthy, successful young man, Dexter continued to display--and to make life choices--as the result of his basic restlessness and discontent. It was his essential discontent, his need to reach for a romantic and more vibrant existence, that fed Dexter's obsession with Judy. She became the incarnation of all his fearly winter dreams, and he lived in them and for them for the remainder of his life, until the day in New York when Dexter's romantic dreams were destroyed by reality.