Literary Analysis Questions – “Winter Dreams”
Directions: In your small group, discuss and answer each question. You will have a time keeper, a
recorder, a speaker, and someone to find the textual evidence. You will only need to have one
answer sheet with all group members’ names on it.
1. What is a winter dream? Is the title appropriate for the story? What is/are Dexter‘s dream(s)? Why? Do his
dreams fit his reality?
2. What, exactly, are Dexter’s winter dreams? Explain.
3. The first line of the story states that “Some of the caddies were poor as sin.” What does this suggest about
the characters and how does it help to establish a theme for the story?
4. After quitting his job as a caddy, the narrator tells us that “the enormity of his decision frightened him.”
Explain this comment. Why did he quit his job anyway?
5. What type of person is Dexter? How does the narrator feel about Dexter?
6. “Careless” is a word frequently used in the text. Discuss how this word plays into the meaning of the story.
7. Dexter says he is newer and stronger than the careless, wealthy people he meets. What makes him so? Why
then does he want his children to be like the careless, wealthy people?
8. How does Judy function in the story? Explain, providing examples from the text. Perhaps focus on Dexter’s
comments about her, the narrator’s commentary, and her own actions/voice throughout the text.
9. Explain how the narrative voice functions in this text. Look through the text and find examples of the
narrator’s voice and notice how he/she is speaking to us, the reader. What affect does this have and why
does Fitzgerald include or write the narrator this way?
10. Dexter refers to Judy using a series of metaphors: “He knew that Irene would be no more than a curtain
spread behind him, a hand moving among gleaming tea-cups, a voice calling to children...” What do these
metaphors suggest about how Dexter views Judy?
11. Why is Judy Jones usually referred to by her first and last name?
12. Explain what makes Dexter cry at the end of the story.
13. Explain the role that dreams played in Dexter’s life and the way that the loss of these dreams has affected
him (not the fact that he cried, but affected his views about life/existence, etc.). Pay special attention to the
last page and Dexter’s closing comments here.
14. The story is divided into six parts. What is the significance of each part?
15. Fitzgerald uses anaphora in “Winter Dreams” to create meaning. Looking at the examples on pages 8 and 9,
explain how the anaphora adds emphasis and meaning to this section of the story.
16. Is “Winter Dreams” a cautionary tale, a moral lesson, or something else? Explain.