Winter Dreams

“Winter Dreams” takes place mostly in Minnesota, which is known for its cold, gloomy winters. The title evokes longing for the spiritual rebirth associated with spring: “Winter dreams” look forward to glistening light and warmth amid the dullness of winter.

The story unfolds in the third-person limited perspective of Dexter Green, a young man who aspires to win over the beautiful and seductive Judy Jones. From its outset, “Winter Dreams” draws a distinct contrast between the caddies who are “poor as sin” and Dexter Green, who “only caddie[s] for pocket money” (662). This juxtaposition introduces a key theme of the story: the social significance and power tied to wealth. Dexter’s employment at the club also provides a clue to the content of Dexter’s winter dreams, as Dexter imagines becoming a golf “champion” and gaining the admiration of golf club patrons such as Mr. Mortimer Jones.

Dexter’s dreams of wealth and fame are inseparable from his pursuit of Judy Jones. When Judy is first introduced, she is presented as commanding and controlling. Not only does she mistreat her nanny, but she addresses Dexter condescendingly as “Boy!” Also pertinent is the nanny’s remark that Mrs. Mortimer Jones sent them to play golf, which hints that Mr. Mortimer Jones, one of Dexter’s clients and a man whom he emulates, is Judy’s father. Although Dexter has already achieved success a caddy and earned the respect of golf club patrons by never losing a ball, he receives a “strong emotional shock,” from his encounter with Judy Jones (664). Subconsciously, Dexter quits his job because he does not want to caddy for Judy. After all, if he were a caddy for Judy, he would never have a chance of marrying her.

From this point forward, Dexter strives to become the very best and forms the habit of comparing himself to wealthy and powerful men. For Dexter, Judy represents eternal wealth, youth, and beauty. Although Dexter does not say it outright, Judy becomes an idealized embodiment of American success, and winning her over would mean he has “made it.”

When Dexter returns to the Sherry Island Golf Course at age 23, this time to play a round of golf rather than serve as a caddy, Judy Jones reappears, now a beautiful young woman. Although her callousness is clear—she accidentally hits one of Dexter’s golf partners in the abdomen with a golf ball and does not appear bothered by it—many of Dexter’s acquaintances speak of her physical attractiveness, and this social approval enhances her appeal to Dexter.

When Judy approaches Dexter on her boat, she indicates she is avoiding a man because he referred to her as his “ideal.” Dexter too regards Judy as his ideal: Although he feels superior to other men, he is subject to the same illusions as they are. His dinner with Judy underscores the parallels; Dexter is disappointed to find Judy wearing a “blue silk afternoon dress” rather than “something more elaborate” (666). His expectations of cocktails and a butler similarly go unfulfilled. Dexter expects the most romanticized version of his evening with Judy (and of his relationship with Judy in general). The disparity between Dexter’s dreams and reality is an ongoing theme throughout the story.

This disparity becomes even clearer when Judy “slips into a moody depression” (667). After dinner, Judy not only acts in a manner contrary to the loveliness Dexter expects, but she complains about the “shock” of finding out a man she cared about is “poor as a church-mouse” (667). In the ensuing conversation, both characters emphasize the value of wealth. Judy overtly asks Dexter whether he is poor, and Dexter responds by describing himself as wealthy, successful, and capable of achieving even more in the future.

That Judy kisses Dexter once she finds that Dexter is wealthy highlights the superficiality of the so-called American dream, in which wealth takes precedence over love. By suggesting that Judy’s kisses arouse “surfeit” in Dexter, Fitzgerald compares them to money or material possessions. Judy’s kisses are a status symbol. The more a person has, the more a person wants (and the more embedded wealth and status are into the person’s sense of self). For Dexter, the moment when he and Judy are together is a “moment he control[s] and own[s]” (667), but his sense of security and wealth is fleeting. The text later says of Judy’s kisses that “[t]he helpless ecstasy of losing himself in her was opiate rather than tonic” (668). In other words, Judy’s love is addictive. It demands more and more fuel and brings distress to the person with the addiction. Dexter’s sense that he may finally control and own the glittering persona of Judy Jones comes crashing down when Dexter realizes Judy is seeing other men as well.

Left to reconcile his winter dreams with the reality of Judy’s aloofness, Dexter ultimately decides to settle for a woman who is kind and sweet but, in his eyes, ordinary. Again, Judy has caused Dexter to make a rash decision; figuratively, he quits being Judy’s caddy again, as he decides to stop following and catering to her. In trading “an old penny’s worth of happiness for this bushel of content” (669), Dexter demonstrates that despite his winter dreams, he is ultimately a realist who would rather pursue a more contented and balanced life.

On the night Dexter reunites with Judy at the University Club, he is again “unconsciously dictated to by his winter dreams” (664). In essence, Judy is an extension of his own egoic pursuit of wealth, status, and transcendence, as he believes she is “his girl, his pride” (671). Although his actions hurt kind people such as Irene and Irene’s parents, Dexter does not experience remorse, and when Judy and Dexter’s short engagement falls through, Dexter does not blame Judy. He moves on and continues to achieve financial success, feeling that “no barriers [are] too high for him” (671). However, Dexter continues to look back fondly on his moments with Judy. Because Judy’s appeal is based not on her personality and actions but on her wealth, youth, and beauty, the breakup does not diminish her allure. Dexter continues to cherish memories of Judy and is on his way to becoming one of the dozen or more men who carry “the memory” of Judy’s smile “into middle age” (663).

Dexter’s belief that Judy exists somewhere as he remembers her is akin to Gatsby’s symbolic green light in Fitzgerald’s The Great Gatsby. It is Dexter’s beacon of hope and faith: his religion and his sense of spirituality. Learning that Judy’s beauty has faded and that she has become ordinary taints Dexter’s memories and destroys his dreams. It mocks him by indicating that Judy was never transcendent or special to begin with, and it undermines Dexter’s sense of exceptionalism by extension. Dexter feels like “getting very drunk” to counteract the sobering reality of this realization (672). The almost oxymoronic image of the sun sinking “in dull lovely shades” juxtaposes the dullness of reality with the loveliness he remembers (672); it evokes the sense of winter returning, with Dexter’s dreams no longer alive to palliate the death and decay the season brings.