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In winter, Dexter Green, son of the owner of the second-best grocery store in Black Bear, Minnesota, skis across the snowed-in golf course where he caddies in the warmer months to earn his pocket money. In April, the spring thaw begins and the first golfers brave the course. Unlike the dismal spring, the autumn and winter empower Dexter and stimulate his imagination. Dexter imagines beating the golf club’s most esteemed members. At work, he crosses paths with Judy Jones, who, attended by her nurse, asks Dexter to carry her clubs. Dexter can’t leave his post, and Judy throws a tantrum and tries to strike her nurse with her clubs. When the caddy-master promptly returns and Dexter is free to be Judy’s caddy, he quits. Hastily ending his employment as a caddie is the first in a lifelong series of impetuous acts that would be dictated to Dexter by his so-called winter dreams, which drive him to desire material success.

Dexter foregoes state school for a more esteemed eastern university, where his financial resources are stretched. He still longs for luxury, but his desires are often denied. After college, Dexter, articulate and confident, borrows $1,000 off the strength of his degree and buys a partnership in a laundry. By age twenty-seven, he owns the largest chain of laundries in the upper Midwest. He sells the business and moves to New York.

We learn more about a period of time during Dexter’s rise to success. At age twenty-three, Dexter is given a weekend pass to the Sherry Island Golf Club by Mr. Hart, for whom Dexter used to caddy. Dexter feels superior to the other competitors but also that he does not belong in this world. At the fifteenth green, while the group searches for a lost ball, Mr. Hedrick is struck in the stomach by Miss Jones, who wishes to play through and doesn’t realize that she has struck another player. She hits her ball and continues on, as the men alternately praise or criticize her beauty and forward behavior. Later that evening, Dexter swims out to the raft in the club’s lake, stretching out on the springboard and listening to a distant piano. The sound of the tune fills him with delight at his present situation. The peaceful scene is disturbed by the roar of Judy’s motorboat. She has abandoned a date who believes that she is his ideal, and she asks Dexter to drive the boat so that she can water-ski.

Waiting for Judy to arrive for their date the next evening, Dexter imagines all the successful men from esteemed backgrounds who had once loved her. He has acquired polish and sophistication despite his humble origins. Judy arrives in modest clothes, tells the maid that dinner can be served, and informs Dexter that her parents will not be in attendance, which is a relief for Dexter. After dinner, on the sun porch, Judy asks Dexter whether it is all right if she cries. A man she was dating has confessed he is poor. When she asks Dexter what his financial standing is, he tells her that he is most likely the richest young man in the entire region. They kiss, and Dexter’s passion for her increases. Dexter continues his pursuit of Judy, but during a picnic she leaves with another man. She claims that nothing has happened between her and the other man, which Dexter doesn’t believe.

Judy toys with the various men who seek her affections. The summer ends, and Dexter takes up residence at a club in town, showing up at the dances when Judy is in attendance. He still desires her and dreams of taking her to New York to live. He eventually forces himself to accept the fact that he will never possess her in the way he wants. He throws himself into work and becomes engaged to Irene. One night, just before the engagement is to be announced, Irene’s headache forces her to cancel her plans with Dexter. He return to the University Club, where Judy, back from her travels, approaches him. They go for a drive. Judy flirts with him, telling him he should marry her, and they discuss their former passion. She asks to be taken home and begins to cry quietly. She repeats her desire to marry him. She asks him in, and he relents. Later, he does not regret that Judy’s ardor cools after a month, that Irene and her family were deeply hurt by his betrayal, or that his reputation in the city has been compromised. He loves Judy above all. Leaving for the East with the intention of selling his laundries and settling in New York, the outbreak of World War I calls him back west, where he transfers management of his business to a partner. He enters basic training, welcoming the distraction of combat.

In New York seven years later, when Dexter is thirty-two, he is more successful than ever. Devlin, a business associate, informs Dexter that Judy married a friend of his, a man who cheats on her and drinks heavily while Judy stays at home with the children. She has also, according to Devlin, lost her looks. Dexter feels the loss of her beauty and spark personally, because his illusions of Judy are finally and irreparably shattered. He cries, mourning the past and his lost youth, which he will never be able to reclaim.