What does Judy represent for Dexter in "Winter Dreams"? Does Dexter really love her?
For Dexter, Judy Jones is the epitome of the "glittering things and glittering people" of the world of wealth that he covets. It is around her that Dexter creates his "winter dreams." When he first sees the young Judy, Dexter comprehends the power that wealth seems to bestow upon all it touches.
After Dexter makes his fortune, he returns and circumstances bring Judy into his life again, but his dream is ephemeral as she pours kisses upon him when she learns that he is rich, but then flirts with other men. Nevertheless, Dexter "surrendered a part of himself to the most..unprincipled personality with which he had ever come in contact." Judy possesses an excitability that Dexter finds exquisite, but she is only entertained by having her own desires gratified. Despite his disillusions with Judy's world, Dexter cannot be cured of his illusions about Judy.
After Dexter finally despairs of marrying Judy, he becomes engaged to Irene Scheerer; yet, Dexter meets Judy again one night when Irene has a headache. Judy has returned from Florida, and seemingly humble, bemoans that she cannot be happy. "I'd like to marry you, if you'll have me, Dexter." carried off by emotion, Dexter commits himself to his dream. However, it is only a short time before the marriage is over, and Dexter experiences deep pain.
It is several years later before Dexter hears anything about Judy; when he does, it is from a man named Devlin who describes Judy as a faded beauty who is ill-treated by her husband, but she takes the abuse. Angry and feeling a tremendous sense of loss as though something has been taken from him, Dexter recalls the beauty of her neck, the old promise of her kisses, the "plaintive melancholy" of her lovely eyes--"the dream was gone," that certain magic that the rich held for him is lost, and only the solid realities are left to Dexter Green.
Judy represents the uninhibited drama of youth. She is the epitome of carefree, selfish indulgence, and as a result Dexter is more in love with the image of Judy than her real self.
Judy raises a passion within him, which forces him to break off his engagement for a wild liaison when they meet again as adults. They were never really meant for each other, and as he leaves for further adventure in the army, she marries a man who is cruel to her, and she ages badly as a result.. When he learns of Judy’s poor fortunes, his words suggest that he mourns more for the feelings which accompanied her rather than Judy herself:
I cannot cry. I cannot care. That thing will come back no more.
The “thing” is more likely to be youthful passion than a derogatory reference to Judy herself.