Dexter strongly associates money with love in "Winter Dreams." He thinks that if he has money, he can win the love of Judy Jones. One tiny problem: he doesn't get that having money might somehow replace love in his emotional life. So when he dedicates himself to earning money, his ability to love dies away without him even knowing it. He is left instead with "the gray beauty of steel that withstands all time" (6.35). Not even the loss of Judy can get to him. The great irony of Dexter's life is that, as a boy, he links money and love together. But in Fitzgerald's world, money and love are actually mutually exclusive. No one who has a real talent for making money can hang on to their romantic ideals.
By making Judy Jones a two-dimensional character, Fitzgerald emphasizes that Dexter's attraction to her is not personal, but just a symbol of his desire to achieve upper class status.
Dexter's character in "Winter Dreams" suggests that love and desire for money are incompatible. For Fitzgerald, it appears that business success kills off human feeling.