What happens to Dexter and Judy's engagement in Winter Dreams?
I'm not sure Judy ever took their engagement seriously. She flirts with other men and frequently goes off alone with them. After more than a year of watching this kind of behavior, Dexter finally realizes that she is not going to make a serious commitment to him. He breaks off their relationship and becomes engaged to another girl.
However, Judy is, while not ready to settle down, is not ready to let him go either. One night when Dexter goes alone to the club, he runs into Judy again, and the old feelings stir. She convinces him to break off his engagement and renew his relationship with her. But she is no more ready to marry him now than she ever was. After just one month, she breaks things off again.
No one can describe Judy better than the author himself:
She plays the mating game by her own rules, ‘‘entertained only by the gratification of her desires and by the direct exercise of her own charm.’’ Yet, at her core is a hollowness, which she notes when she declares, ‘‘I'm more beautiful than anybody else … why can't I be happy?’’