Let's think about this for a second. Judy Jones is a central character in the story, but what do we really know about her?
Well for one thing, Judy is horrible. We're just going to come out and say it: she is selfish and spoiled – straight out of Gossip Girl. But she pays for all of the casual cruelty of her youth by the end of the story. So in the end we feel sorry for her (even though we still hate her).
We also know that Judy Jones is Dexter's ideal, his inspiration. When he first sees her show up at the Sherry Island Golf Club when she is eleven and he is fourteen (creepy!), he can already see the signs of the great beauty that she is going to be when she grows up. When she throws an absolute hissy-fit and actually tries to hit her nurse on the chest with a golf club, Dexter doesn't think: what a brat! (We do.)
Instead, he decides that he can't be her caddy. He just can't. She obviously thinks that servants are the kind of people she is allowed to hit with golf clubs. If Dexter wants to woo her someday – and boy, does he – he has to join her social class. He has to be a millionaire. He has to quit his job at the golf club and throw himself into the business world ASAP.
So Judy Jones' eleven-year-old tantrum directly inspires Dexter's ambitions to achieve his winter dreams of greatness. And she spurs those dreams on when they meet again when Dexter is twenty-three and Judy is nineteen. Dexter has made a name for himself; now he can court her, and she does seem to be attracted to him. But Dexter soon realizes that he will never be able to call Judy his own.
The problem is, Judy's beauty and money guarantee that she has everything she wants. Because she can (and does) have all that she desires, she is fickle. She's never quite satisfied because "She was entertained only by the gratification of her desires and by the direct exercise of her own charm" (4.5).
In other words, Judy is super self-absorbed. Because Judy never has to try for anything, she doesn't understand real value. She is perfectly happy to keep Dexter hanging around for a bit, but he is always one of many other lovers, whom she kicks to the curb whenever she wants. Eventually, Dexter wises up and decides that he needs a more lasting relationship and leaves Judy behind.
But Judy won't be denied. Sometime later, Judy reappears in Dexter's life and she seems unusually sad for some reason. She weeps, "I'm more beautiful than anybody else […] why can't I be happy?" (4.61). Wait a minute. Judy is unhappy? How can the girl who has everything be unhappy?
Judy's sudden despair points out the basic problem of "Winter Dreams." In a way, Judy has already achieved Dexter's winter dreams. She has everything she wants – cash and sex appeal – but there is still some nameless longing in her heart. Like Dexter, she has this desire for something different; she just can't imagine what it is. Her winter dreams lack a goal, which begs the question: are they even dreams at all?
Judy tries again with Dexter. Perhaps she's thinking that if she's not alone, she'll be satisfied. But she breaks off their engagement after just a month. Whatever Dexter has to offer, it can't fill the emptiness at the core of Judy's character.
What makes her so restless? Why can't she settle with Dexter, who certainly has a lot to offer?
Here's a theory. Judy has been brought up in a system of consumption. Let's explain: not only is she a consumer, who can buy whatever she wants, but she is also consumed. She's an object of desire for all the men around her. Everyone wants to sleep with her, and she has had dozens of lovers. She knows and uses the power of money and her beauty. But she doesn't seem to know anything about herself, about what she wants outside of all of these men and all of these material possessions.
To put it another way, Judy is a blank character. She is a screen onto which men like Dexter project what they most want to see: beauty, romance, soul. We never really see what she's like when she's alone and not being watched by desiring men. In some ways, she is as two-dimensional a character as her father or T.A. Hedrick: she's just there to spur on Dexter's own fantasies.
In the end, all we really know about Judy is that her endless search for satisfaction seems to burn itself out by the end of the story. She marries a businessman from Detroit, Lud Simms. She has lost her looks and devoted herself to her children. Her husband drinks too much and sleeps around.
Judy may be happy and she may not be. Who knows? Certainly, Devlin, who reports all this news to Dexter, feels "sort of sorry for her" (6.7). But the real point is that the fact that Judy has settled down into this lackluster existence makes Dexter realize that he is also no longer searching for a better life. He has given up his own romantic ideals, too. He's settled for less that what he aimed for.
Judy Jones, the symbol of Dexter's larger-than-life dreams has now become boring Judy Simms. She's the dream disappeared. And because she is never fleshed out as a real, three-dimensional person, we can't muster much sympathy for her. We're more focused on Dexter, who at last has to face up to the fact that the dream he has been chasing for all these years has always been an impossibility, no matter how much money he's made.Timeline