Consider stereotypes of masculinity in society today. How are these stereotypes enacted in Walter Mitty's dreams? How do these stereotypes differ from his everyday behavior?

Do you think Thurber's characterization of Mrs. Mitty is sexist? What sort of picture of marriage emerges in the story, and how does that picture compare with what is considered a "typical" marriage in American society today?

List the details which connect Walter's fantasies and his reality together. Analyze the significance of these details to the story's overall theme.

Investigate American society during the end of the depression and the beginning of World War II. Do you think Thurber accurately portrays middle-class life during that time in "The Secret Life of Walter Mitty"? Why or why not?