Discuss the portrayal of women in Winesburg, Ohio.
Compare and contrast Seth Richmond and Elmer Cowley, particularly in their attitudes toward Winesburg and George Willard.
Discuss the role of loneliness in the book. Who is lonely? Who isn't?
Are there any happy characters in Winesburg, Ohio? Who are they? Defend your answer.
Discuss the overall structure of the stories. Why do you think Anderson arranged them the way he did?
Discuss George Willard's relationships to women, particularly his mother, Kate Swift, and Helen White.
To what extent are the characters "grotesques"? How does this image play out throughout the book?