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.