What major events happen in each season that reflect Dexter's moods in "Winter Dreams"?
Dexter meets Judy Jones for the first time in the spring on the golf course at the Sherry Island. She is a spoiled little rich girl; Dexter is a poor caddy. Dexter quits his job rather than "work" for her. Dexter rejects his social class. In his winter dreams, he longs to be a part of the rich and "glittering" life Judy represents.
Dexter meets Judy for the second time years later in the summer--again on Sherry Island. Dexter has graduated from college and made money in business. He is at the club as a guest now, not as a caddy in service to the rich. His time on the lake in the moonlight with the sound of piano music drifting across the water fills him with "a sort of ecstasy" as "everything about him was radiating a brightness and a glamour he might never know again." The romance and glamour he had dreamed about surround him. It is at this moment that he meets Judy again as she appears out of the darkness in a speed boat. She becomes part of the glamour he always sought.
Dexter begins his relationship with Irene in the autumn more than a year after Judy had moved on to another man. His dream of her remained alive, but he had accepted that he would never have her.
In the winter, Dexter and Irene become engaged, planning to announce it in June and be married three months later. That winter lasted a long time for Dexter, prolonging itself "interminably." It took that very long winter for Dexter to develop "a certain tranquility of spirit" in his life without Judy. However, he still had not given her up in his heart; she had become synonymous with all his winter dreams:
The thing was deep in him. He was too strong and alive for it to die lightly.
Ironically, Dexter meets Judy once again in the spring, just as he had met her for the first time in the spring. Breaking his engagement to Irene, Dexter goes back to her. Judy's interest in him lasts only one month, but Dexter did not regret his time with her:
He loved her, and he would love her until the day he was too old for loving . . . he tasted the deep pain that is reserved only for the strong, just as he had tasted for a little while the deep happiness.
Dexter's relationship with Judy kept him on a continuous emotional roller coaster, from beginning to end. Finally, he has only his memory of her, but he loses that, too, in the story's sad conclusion.