1. Discuss Anderson's attitude toward the small town. Is Winesburg, Ohio an exposé of small-town narrowness or a nostalgic re-creation of small-town virtues? (If you have read some other descriptions of small-town life you might want to compare them with Anderson's. Among possible choices for such a comparison, consider Edgar Lee Master's Spoon River Anthology, Edwin Arlington Robinson's poems about people in Tilbury Town, Sinclair Lewis's Main Street, or Thomas Wolfe's Look Homeward, Angel.)
2. Discuss how form and content are unified in Winesburg. Consider the form of the tales and, also, the book as a whole.
3. Discuss the use of symbolism in Winesburg, Ohio. (Consider darkness, hands, rooms, doors, snow, rain, etc.)
4. What elements in Winesburg might lead you to call it realistic? In what way is it not realistic?
5. Explain with examples from various stories what Anderson means by "grotesques."
6. Discuss the influence of Anderson's life on Winesburg, Ohio.
7. How does George Willard develop in Winesburg. Refer to specific stories to show what causes this development and how it is evidenced.
8. Discuss the reasons for isolation shown in the book and consider whether Anderson offers any solution to the problem.
9. Discuss Anderson's attitude toward each of the following: sex, religion, material success.
10. Is there any significance to the names of characters in Winesburg? Defend your answer.
11. Define irony and discuss its use in the book.