1. 1) 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?
2) What type of character is Judy Jones? Identify the many nuanced ways in which Judy Jones is described. How do the descriptions help to define her? (nuanced: a subtle difference or distinction in expression, meaning, response, etc / implication or hint)
3) Why is Judy Jones usually referred to by her first and last name?
4) What type of person is Dexter? How does the narrator feel about Dexter?

2. 5) What is a winter dream. Is the title appropriate for the story
5) 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?
6) Is “Winter Dreams” a cautionary tale, a moral lesson, or something else?
7) “Careless” is a word frequently used in the text. Discuss how this word plays into the meaning of the story.
8) 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?
9) The story is divided into six parts. What is the significance of each part?

3. Read the essay "What is The American Dream?"

4. Paragraph 1
Analyze the various ways in which the American Dream has been defined over the years.
Analyze how wealth and class and society relate to the idea of the American Dream.
Paragraph 2
Discuss F. Scott Fitzgerald’s commentary regarding the American Dream based on his portrayal of Dexter and his surroundings.
How does Dexter define the American Dream for himself and what sacrifices does he make to achieve it?