In "Winter Dreams," Dexter Green's life is shaped by his ambitions and affections, which intertwine with the changing seasons and his encounters with Judy Jones. Dexter's journey spans from his youthful days as a caddy, dreaming of success, to his later years as a businessman grappling with the loss of his dreams. His story is a reflection on ambition, desire, and the bittersweet nature of maturity.

Early Aspirations

At fourteen, Dexter Green works as a caddy at the Sherry Island Golf Club. Unlike his peers, Dexter's time there is not driven by necessity; his father owns a thriving grocery store, second only to the best in Black Bear. The wintertime transforms the golf course into a snow-covered expanse, where Dexter often skis, feeling a deep sense of melancholy. As he glides over the fairways, he dreams of becoming a champion golfer, imagining himself besting the affluent club members. His departure from caddying is sudden, sparked by an encounter with an eleven-year-old Judy Jones, whose dismissive behavior compels him to quit on the spot.

Ambitious Transitions

Several years pass, and Dexter makes a bold choice to reject the state university his father offered to fund. Instead, he sets his sights on an esteemed college in the East, despite financial constraints. The narrator emphasizes Dexter's focus on acquiring wealth, rather than merely mingling with the elite. Armed with a college degree, Dexter borrows money and invests it in a laundry business, driven by his entrepreneurial spirit. His hard work pays off, and by age twenty-seven, Dexter has succeeded in building a successful chain of laundries.

Rediscovering Judy

At twenty-three, Dexter is invited to play golf at the Sherry Island Golf Club, reconnecting him with his past. During the game, Judy Jones inadvertently hits a fellow player with her ball, leading to another encounter. Later, as they swim, Judy invites Dexter to join her boating, and he finds himself once again captivated by her charm. An invitation to dinner the following night leaves him feeling as if her whims have once again altered the course of his life. After a magical evening together, Dexter realizes that he has been infatuated with Judy since childhood.

The Allure and Elusiveness of Judy

Over the ensuing weeks, Dexter and Judy spend considerable time together, yet her attention remains fleeting. Judy's tendency to flirt with other men becomes apparent, revealing her fickle nature. After a year and a half, Dexter resigns himself to the fact that Judy cannot commit, and he turns his attentions to Irene Scheerer, whom he finds "sweet and honorable." As spring arrives, Dexter plans to announce his engagement to Irene, but a chance meeting with Judy at the University Club reignites old feelings. Despite his attempts to remain composed, Judy's declaration of love persuades him to break off his engagement with Irene in favor of rekindling his romance with Judy.

Illusions Shattered

Judy’s renewed interest in Dexter proves short-lived, lasting merely a month, yet Dexter harbors no ill will towards her. Soon thereafter, he moves to the East with intentions of settling in New York, only to enlist when World War II erupts. The war offers Dexter a reprieve from his emotional entanglements, freeing him from the confusion Judy left behind.

Confronting Reality

Seven years post-war, Dexter has returned to New York, boasting even greater success than before. A business meeting introduces him to a man named Devlin, who mentions that Judy married his best friend. Devlin's offhand comments reveal that Judy's husband mistreats her and that she remains at home caring for their children. The news that Judy's beauty has faded hits Dexter hard; the "pretty girl" of his memories now appears diminished. Faced with this change, Dexter feels the painful loss of his "winter dreams," realizing that his youthful ideals have crumbled. Overwhelmed, he mourns not for Judy, but for the demise of his dreams, understanding that "that thing will come back no more."