The world shown in "Winter Dreams" places a primacy on being young. Dexter is at the pitch of prosperity as a young man. Judy Jones controls the gaze of other people as a young woman. Even when Dexter is poor, it is the firm determination of his youth that enables him to better himself. The characters in Fitzgerald's creation place a great value on being young, and youth is synonymous with opportunity, the time of life to make emotional commitments, and a sense of no boundaries.
Aging is shown to be something entirely different. Fitzgerald illuminates the social expectation and attitude towards becoming old. As an older man, Dexter is accompanied only by the pain of his "winter dreams." For Dexter, being old means "that thing is gone." Judy suffers the most as she gets old. Judy's husband Lud Simms drinks too much and cheats on her while she stays home with their children. It does not escape Fitzgerald's perception that women lose more as they get older than men.
Dexter becomes older and must deal with emotional loss. Judy becomes old and finds that her beauty has evaporated with age. In "Winter Dreams," Dexter and Judy find that a world predicated upon external success and appearances does not look kindly upon becoming old.