Bring on the tough stuff - there’s not just one right answer.
Fitzgerald spends a lot of "Winter Dreams" looking at Judy Jones. We get tons of descriptions of her physical appearance and her manners. But we never get much of a sense of what she is like on the inside. Can you imagine "Winter Dreams" from Judy Jones' perspective? How might her point of view change the overall tone of the story? How do you think Judy might describe Dexter Green?
How would "Winter Dreams" be different if it maintained the exact same rags-to-riches plot line, but with a woman protagonist instead of a man? Would such a plot be possible for a short story written in 1922? What would Fitzgerald have to change to make "Winter Dreams" work with a female main character?
Fitzgerald has said that "Winter Dreams" was the beginning of his idea for his most famous novel, The Great Gatsby (1925): ambitious guy from the Midwest tries to make it in East Coast high society, and all for love of a (rather cruel) girl. But The Great Gatsby's plot departs from "Winter Dreams" in a couple of key ways. How does the introduction of Nick Carraway as the frame narrator affect The Great Gatsby's tone? What are the similarities and differences between Dexter Green and Jay Gatsby? Why might Fitzgerald have made these changes in revising "Winter Dreams" into a much longer novel?
"Winter Dreams" is technically a third-person story. Dexter is described as "he," rather than speaking as "I." But the story very much focuses on Dexter's personal experiences and feelings. How much would "Winter Dreams" change if it were told directly from Dexter's point of view? How would the tone of the story be different if it appeared from a truly objective third-person perspective? Do you think this style of narration generates more or less sympathy in the reader for Dexter?
"Winter Dreams" portrays Dexter's disappointment with East Coast high society by showing us his heartbreak at the fall of his ideal woman, Judy Jones. But there are other ways that Fitzgerald could choose to depict Dexter's disappointment: for example, he could lose all his money or face social discrimination for his lower class origins. How would the message of "Winter Dreams" change if there were no love plot in the story? Why might Fitzgerald choose to tell a story about social class using romance?
How would "Winter Dreams" be different if Dexter had married Irene Scheerer after all? Would he have been able to achieve his life's ambitions with Irene by his side? Why or why not? What might Fitzgerald be saying about the relationship between a happy family life and ambition?