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Dexter Green is a fourteen-year-old caddy at the Sherry Island Golf Club in Black Bear, Minnesota. His father owns the second best grocery store in town, so Dexter is solidly middle-class—comfy, but by no means rich. One day, when he is caddying at the golf course, he meets the lovely(ish) Judy Jones. At the sight of Judy, he decides to quit his caddying job. He resolves to follow his "winter dreams" to become the kind of man who would fit into Judy Jones' wealthy world.
Years later, after college, Dexter invests in a laundry business in the city nearest to Black Bear. It's not the sexiest job in the world, but he makes a boatload of money and starts hanging out with the wealthy families of Sherry Island. He meets Judy Jones a second time, when she accidentally hits one of Dexter's golf companions in the chest with a golf ball (ouch). Later that evening, Dexter bumps into Judy on a raft in the middle of Black Bear Lake. She asks him to join her for dinner, and Dexter eagerly accepts.
At dinner, Judy confesses that she is a bit blue because a man she really liked turns out to be poor. The horror! When Dexter assures Judy that he is well-off, she leans over to kiss him. Dexter realizes that he has wanted Judy Jones every since he was a teenager.
At this point, Dex is head-over-heels in love with Judy. Even though he knows that she has other lovers, he puts up with it. But after a year and a half, Dexter finally gets it: Judy doesn't actually care about him. At all. She will never return his feelings. So he gets engaged to Irene Scheerer, a nice (but slightly less attractive) girl with a friendly, welcoming family. But not so fast: when Judy turns up again asking Dexter to marry her (not cool, Judy), Dexter practically trips over Irene to begin, once again, his affair with Judy Jones.
Judy and Dexter's rekindled romance only lasts for a month. He moves east to New York the following year, and when the Americans join World War I, Dexter signs up for the Army. He is glad to have a distraction from his pathetic personal life. The poor guy actually prefers trench warfare to "webs of tangled emotion." (5.4)
Flash forward seven years from Dexter's failed engagement to Judy. Dexter is thirty-two. He hears from one of his business associates that Judy Jones has become Judy Simms. Mr. Simms apparently drinks too much and cheats on her. Oh, and one other thing: she's not the cutie patootie she once was. Dexter is horrified to hear that Judy's beauty has faded. He understands that his "winter dream" has gone forever: he is no longer the idealistic young man who loved Judy Jones.