The new status also brings Dexter new meeting with Judy Jones, with whom he has strange and complicated relationship: once they are together, but then they break up, Dexter and Judy struggle with contradictions between reality and fantasy. Nevertheless it is Judy Jones who is the second main dream of Dexter, as she represents to him the best in a woman. Frustration and failure in love has become fatal for the hero, and he can’t become happy despite his wealth. That is why Dexter leaves his business and his love, and goes to fight in the World War I.
The resolution of the conflict has become final part of the story, when Dexter lives in New York and is very successful. Though news about Judy again make him suffer, as he understands that his illusions and dreams of Judy are finally destroyed. He feels great frustration about his past and his lost youth, when he lived in dreams which never came true.
The story “Winter Dreams” primarily tells us about the dreams of the main character, who basically lives in his illusions and dreams. From early childhood Dexter’s life is characterized by his dreaming: the first very aim of his life is to achieve wealth and success, to have all the best of everything; and the second dream has become Judy Jones, whom he has been in love with through all his life. But in fact Dexter faces numerous contradictions between his dreams and reality, and finally frustration of that dreams becomes the biggest disappointment in life.
In “Winter Dreams” Fitzgerald has shown the theme of his time, as the problem of “American dream” and its failure was inherent to many Americans in the early 20th century. The desire for wealth and beautiful life, glitter and glamour attracted thousands of young people. Fitzgerald in his hero showed the essence of illusory American dream of wealth and status. Dexter with his dreams of success is embodiment of his generation, who saw unlimited opportunities in the new century, but had false dreams and aspirations.
Bruccoli Matthew J. The Short Stories of F. Scott Fitzgerald: A New Collection. Scribner, 1995