“Winter Dreams” by F. Scott Fitzgerald – Study Questions
Due by midnight, Friday, April 3

You may type directly on this file, save it, then attach it (use the paper clip icon on your school email), and send it back to me via email. You may also use Genius Scan (free app) or your phone camera to fill it out by hand and text it to me. You have my cell number. Don’t hesitate to contact me if you need help or just to say hello. I miss you guys!

1. Reading Check
a. How does Dexter’s 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?
d. Is Dexter sorry later that he broke off his engagement to Irene?
e. At the end of the story, what has happened to Judy?

2. Did you sympathize with Dexter Green for his tangled feelings toward Judy Jones? Explain why or why not.

3. What details does the author, Fitzgerald, use to persuade us that Dexter is an ambitious young man?

4. What does the story suggest are Dexter’s motivations?

5. Explain how Dexter’s actions reveal his deepest motivations and conform to what the narrator and the other characters say about him.

6. In Richard III, Shakespeare refers to “the winter of our discontent.” How do Dexter’s “winter dreams” reflect his discontent?

7. Does Dexter’s sense of “not having it all” die down when he fulfills his ambition to become rich? Explain.

8. When they meet again as adults, Dexter decides that he has “wanted Judy Jones ever since he was a proud, desirous little boy.” What does Judy represent to Dexter?

9. Explain why you think Dexter really does or does not love Judy Jones.

10. What makes Dexter “newer and stronger” than the wealthy people he meets?

11. Why, then, does Dexter want his children to be like those people?

12. 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.)

13.. What, if anything, do you think is left out of Fitzgerald’s vision of the American Dream?

14. Why do you think Dexter feels a profound sense of loss when he hears about Judy at the end of the story?

15. Do you think Dexter would have been happier in the end if Judy had married him? Why or why not?

16. 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.

17. Most people can identify with this story because they’ve experienced an infatuation with someone who didn’t really return the interest, or worse, acted interested, then disinterested, then interested again, like Judy was to Dexter. Write a paragraph or two about a friend or yourself (do not identify anyone, please) who could not get over a crush on someone, even when that crush mistreated this friend (or you) over and over again.