1. 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.
2. Judy Jones is an attractive woman who receives attention from many men throughout the story. Despite her beautiful appearance, she is superficial and callous. She is also an aggressive woman who goes after any man she desires but is not a joyful person. Judy is a fickle woman who is never satisfied. Her beauty is only skin deep, and she turns out to be an unhappy person.
3. To a great extent, insight has been gained into Dexter through their last interactions. Dexter understands that Judy will not change and that there will not be much in way of a real relationship between both of them. Dexter recognizes that physical separation is the only way he can be "cured" of his fascination with Judy. Fitzgerald coincides this with the break of war, suggesting that Dexter was "welcoming the liberation from webs of tangled emotion." This helps to bring to light how Dexter needed a massive break with his reality laced with Judy. At this point, the realization gained is that Dexter will end up living his life in some form without Judy. It will also set up the invariable ending, which, in true Fitzgerald fashion, elevates tragic conditions in the realm of subjectivity. In terms of what is gained about Judy, the short answer would be that little has changed within her. She is still the same woman she was in terms of her effect on men and the self- indulgence with which she carries herself. In terms of both of them, the reader gains the insight that they are meant to pass as two ships in the proverbial emotional night.
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