Winter Dreams by F. Scott Fitzgerald

In the short story Winter Dreams, Fitzgerald uses the character Dexter Green and Judy Jones to highlight some context of the early American society just prior to First World War and slightly after the war. He uses the interactions between the characters to highlight the rise of the United States to a powerful economic position after the war. In fact, it will take a keen eye to recognize that Dexter represents the middle class in both social and economic aspects of the society largely. Even so, Fitzgerald’s characters are also used to analyze some values and beliefs of the early American society.

As the story begins, Dexter is an adolescent boy working part-time as a caddie in order to raise some pocket money. His father is represented as the proprietor at one of the grocery stores that is doing significantly well in the town. While attending to his duties as a caddie, Dexter has a crush on Judy Jones. Dexter later quits his job to avoid working for Judy for whom he has openly fallen One may observe that although Dexter appears to an ambitious young boy during this time, Fitzgerald uses him to represent both the generation of Americans who set their eyes on a goal and do everything to achieve that goal. That was a goal Dexter was going to gamble with, and as in business, he was the entrepreneur who took uncalculated risks.

He later meets Judy after college while he was in Sherry Island Gold Club. Later, an evening encounter with her seals a date with her. Again, Fitzgerald uses this encounter and the date to highlight the youthful passions and materialistic tendencies as revealed in the character of both Dexter and Judy Jones. Even so, the gamble and the competition soon overwhelm him and since Judy’s heart is still undecided, Dexter settles with Irene. He becomes to her eighteen months later.

However, the return of Judy Jones rekindles the old passions and flames, driving Dexter to break his engagement with Irene. His sacrifice is probably not worth it since Judy once more dumps him a month down the line. His frustrations lead him to join the army to fight in WWI. Dexter becomes successful after the war. Through his friend Devlin, he learns of Judy’s woes. He remembers his youthful mistakes and swears at the end of the story that he wishes not to travel that path again.