This essay analyzes F. Scott Fitzgerald's short story "Winter Dreams" to explore how the protagonist Dexter equates romantic success with social advancement and wealth. Through his interactions with Judy, a woman from an established wealthy family, and his engagement to Irene Scheerer, Dexter reveals his belief that true success requires acceptance by "old money" families. The paper argues that Dexter's ultimate disillusionment stems not from losing Judy herself, but from recognizing that even the most idealized symbol of old money can become ordinary, exposing the fundamental flaw in equating human relationships with material wealth and social status.
The American Dream is a concept uniquely American, suggesting that if a person is willing to work hard enough, they can climb up from their birth station and achieve success. However, this ideal contains a critical limitation: a self-made person—someone born poor who became rich through effort—will never be accepted into groups that focus on "old money." Old money families are those who have been rich for generations and intend to remain so. F. Scott Fitzgerald's short story Winter Dreams exposes this contradiction through the character of Dexter, a young man who pursues wealth only to discover that financial success alone cannot guarantee acceptance into the established wealthy class. Dexter learns to associate true success with winning the heart of Judy, a wealthy woman from an old money family. Through his interactions with women—his initial wooing of Judy, his engagement to another woman, and Judy's subsequent marriage to someone else—Dexter demonstrates that he measures his own worth by the status of the women he pursues and whether they accept him.
At the story's beginning, Dexter is a poor man working as a caddy at an expensive golf course. He meets Judy, the daughter of his employer, and one day is assigned to caddy for her. Unable to accept this role, he announces: "I think I'll quit" (Fitzgerald). This statement is crucial because it reveals that Dexter abandons his only means of support rather than accept a subordinate position in front of Judy. For him, she represents an aspiration, and being seen in a lowly position would force him to admit that he deserves to remain in the lower class.
Dexter's only route to social mobility is to escape his role as a caddy. The confrontation with Judy forces him to take action, marking the moment when ambition overtakes economic necessity. His dramatic gesture—quitting—serves as his first step toward the wealth and status he believes will eventually make him worthy of someone like Judy. In this moment, Dexter equates the woman with the goal itself; winning her becomes inseparable from achieving success.
The next time a woman becomes equivalent to money in Dexter's mind is when he becomes engaged to Irene Scheerer. By accepting Irene, Dexter gains the ability to create a family and home life that should make him happy. However, Irene is not Judy, and she is far easier to win. Her willingness to marry him causes her value to diminish in his eyes because she has not presented a sufficient challenge. Without the difficulty that Judy demanded, Irene compares unfavorably to the symbolic icon of old money that Dexter sees embodied in Judy.
The narrator makes this point explicit: "The fact that Judy's flare for him endured just one month seemed of little importance. Nor did it matter that by his yielding he subjected himself to a deeper agony in the end and gave serious hurt to Irene Scheerer and to Irene's parents, who had befriended him" (Fitzgerald). Though Irene is wealthy, she represents a middle-class existence rather than the vast riches that marriage to Judy would signify. Dexter breaks his engagement and pursues Judy again, proving that he cannot settle for anyone outside the wealthiest families. Class consciousness overrides his capacity for gratitude or loyalty.
Finally, Dexter learns that Judy has married someone else. More devastatingly, he discovers that Judy has lost her beauty and now lives as an ordinary housewife. Yet Dexter's tears do not stem from his inability to have Judy herself. Rather, he weeps because she has revealed herself to be as common as any other woman. The narrator states: "The dream was gone. Something had been taken from him" (Fitzgerald). The dream Dexter mourns is not Judy as a person, but the fantasy of a woman so perfect and mysterious that no man could win her.
"Judy's ordinariness destroys Dexter's fantasy of perfection"
Fitzgerald, F. Scott. "Winter Dreams." Web. 12 Nov. 2012. http://www.sc.edu/fitzgerald/winterd/winter.html
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