“Winter Dreams” by F. Scott Fitzgerald – Study Questions p. 604
Reading Check
a. How does his first meeting with Judy Jones lead Dexter to quit his job?
b. How does Dexter encounter Judy again after nearly a decade?
c. Why does Dexter break his engagement to Irene? Is he sorry later?
d. AT the end of the story, what has happened to Judy?
1. Did you sympathize with Dexter Green in his tangled feelings for Judy Jones? Explain why or
why not.
2. 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.
3. 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.
4. When they meet again as adults, Dexter decides that he has “wanted Judy Jones ever since he
was a proud, desirous little boy” (page 593). What does Judy represent to Dexter? Explain why
you think he really does or does not love her.
5. What makes Dexter “newer and stronger” (page 592) than the wealthy people he meets? Why,
then, does he want his children to be like those people?
6. 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?
7. Why do you think Dexter feels a profound sense of loss when he hears about Judy at the end of
the story?
8. (This is really question #9) – Do you think Dexter would have been happier in the end if Judy had
married him? Why or why not?
9. (This is really question #10) – 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.
