- How and why do the terms Jazz Age and Roaring Twenties relate to Fitzgerald’s writing?
- Are there any autobiographical notes in Winter Dreams? If yes, then which?
- Did you sympathize with Dexter Green in his tangled feelings for Judy Jones? Explain why or why not.
- What details does Fitzgerald use to persuade us that Dexter is an ambitious young man? What does the story suggest are Dexter’s motivations? Explain how Dexter’s actions reveal his deepest motivations and conform to what the narrator and the other characters say about him.
- In Richard III, Shakespeare refers to “the winter of our discontent.” How do Dexter’s “winter dreams” reflect his discontent? Does his sense of deprivation subside when he fulfills his ambition to become rich? Explain.
- What makes Dexter “newer and stronger” than the wealthy people he meets? Why, then, does he want his children to be like those people?
- A recurring theme of Fitzgerald’s work is the pursuit of the American dream. Based on this story, explain what you think Fitzgerald saw as the American dream. (Be sure to include Dexter’s quest for Judy as part of your answer.) What, if anything, do you think is left out of his vision?
- Why do you think Dexter feels a profound sense of loss when he hears about Judy at the end of the story?
- Do you think Dexter would have been happier in the end if Judy had married him? Why or why not?
- Do you think the themes of this story are universal and timeless, or is this a story that could only have happened in its specific time and place? Explain.
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