Olive Kitteridge

Content Warning: This section of the guide contains discussions of mental illness, illness or death, disordered eating, and emotional abuse.

Gather initial thoughts and broad opinions about the book.

1. The novel's structure reflects interconnected stories from different perspectives, all centered around Olive. How does this approach affect your understanding of both the character and the community of Crosby? Have you read other works that employ this narrative technique, such as Sherwood Anderson's Winesburg, Ohio?

2. Throughout the novel, the characters struggle with finding the balance between solitude and connection. Which character's approach to this struggle resonated most strongly with you, and why?

3. The novel presents a candid portrait of aging, loss, and mortality. How did you respond to this aspect of the story, and what do you think the narrative reveals about human resilience?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Olive often puts up emotional barriers (symbolized by her sunglasses) in order to protect herself. Can you relate to this tendency? How do you manage the balance between emotional vulnerability and self-protection?

2. The characters frequently grapple with how their past choices have shaped their present circumstances.