“Winter Dreams” analyzes the motivations and frustrations of two young people coming of age, but it also examines the historical period that is the backdrop to the on-again, off-again relationship between Dexter and Judy. The action in “Winter Dreams” spans the early decades of the twentieth century, from the middle of the first decade to the early 1920s. The so-called Roaring Twenties, the Jazz Age was for some people a time of unchecked hedonism. Self-gratification ruled the day, and for the affluent, it was an era of opulent parties, fashionable trends, and grand social gestures. One critic intimated of the period that it was a time in which people had little concern for the past and even less regard for the future. The time period saw many young people endorse a reckless embrace of the moment, as America emerged from World War I and entered a new and unprecedented economic boom. Fitzgerald emerged as the laureate of the Jazz Age, capturing the spirit of the decade in his fiction while embodying its hedonistic, freewheeling zeal in his personal life as well.
In “Winter Dreams,” as in his fiction in general, Fitzgerald avoided many of the clichéd images of the period, such as flappers, speakeasies, and gangsters. However, in his hands, a certain type of character emerged. Judy embodies all that is stereotypical of the fickle, selfish, and histrionic rich girl. She is in full possession of her beauty and thrall over men, navigating her way through her social world by the force of her charm. She is all appetite, too embroiled in the moment, with little regard for the larger implications of her changes of heart. Dexter is the convert, the middle-class imposter standing outside the dance in the gymnasium and seduced by the wealth and self-indulgence the dancing couples represent. In Fitzgerald’s world, the pursuit of pleasure alienates those who are unable to indulge in escapist acts, which distract from the essential hollowness and isolation that many of his characters try to avoid. Pleasure for pleasure’s sake was the unofficial motto of the flapper, the jazz babies, and the idle rich who helped the twenties achieve its mystique of hedonism and decadence in the major cities of Europe and the United States. In Dexter and Judy, Fitzgerald subtly indicts Jazz Age decadence.