personality, Dexter describes it as "the most direct and unprincipled . . . with which he had ever come in contact." Judy is assertive, unlike many women of the era (including Dexter's fiancee, Irene Scheerer) and goes after whatever she wants "with the full pressure of her charm." He also notes how Judy makes men conscious "to the highest degree of her physical loveliness." On the other hand, she is not a woman who can be "won," and, when men come on to her too strongly, she loses interest. Judy goes through numerous suitors, including Dexter. With Dexter, she has an on-again–off-again affair which culminates in an engagement that never results in marriage.

Judy is aware of her beauty, which she thinks is greater than that of any other woman in her town, but neither her beauty nor her wealth make her happy. The subject of Judy's beauty, however, is entirely determined by who is looking upon her. For Dexter, there is no one more beautiful or more coveted than Judy (though, for him, so much of Judy's beauty and charm is determined by her class status).

Judy may very well have been the most beautiful girl in Black Bear, Minnesota, but Dexter's associate, Devlin, finds that she was "a pretty girl when she first came to Detroit" but is merely "all right" now. Devlin's comment about Judy's looks disillusions Dexter and helps him realize that he idealized Judy as part of his dream that he could hold on to the past and regard himself, still, as a young man with plenty of time to create more future plans. For Dexter, those plans involved owning all of the "glittering things" which belonged to the upper class, including Judy. When Dexter learns that Judy has aged and leads an unhappy life with an alcoholic, he realizes that he, too, is growing older and that his career is no longer "largely a matter of futures." He also realizes that his image of Judy as a coveted object never accounted for her humanity.

In Fitzgerald's short story "Winter Dreams" Judy Jones is presented to the reader as a spoiled little brat who becomes a spoiled teenager and woman. But despite her behavior, Judy continually draws people to her because of her beauty and wealth. ("She has a ghastly reputation but is enormously popular.") However, in the end she is lonely and unfulfilled. Her money gives her no comfort or companionship, and the bloom of youthful beauty has wilted.

Judy has "married well" but Dexter learns how hollow and dissatifying her life has become. Through a third party, Devlin, Dexter discovers Judy has a terrible marriage, has to stay home with the kids, and has lost her looks.

It is startling news to Dexter, who recalls Judy (and anywhere Judy happened to be) as being "mysterious and gay" and "pervaded with a melancholy beauty."

As for Dexter, his dreams of becoming weathly have come true, but he is just as lonely as Judy. He toils in a drab office building. He has not won Judy nor any other beauty. All of his "winter dreams" have faded and died, never to know the light of Spring.