1. How does Elizabeth Strout use the character of Lucy Barton to explore the concept of empathy? What did you learn about your own capacity for radical empathy?

2. How does the murder investigation affect the dynamics between the characters, particularly Bob Burgess and Lucy?

3. Discuss the relationship between Lucy and her ex-husband, William. How does their past influence their current interactions? Have you ever been involved in a similarly complicated and shifting relationship, romantic or otherwise?

4. How does Strout explore the theme of isolation in the novel? Which characters do you think feel the most isolated, and why? How does this theme show up in your own life?

5. What role does the town lawyer, Bob Burgess, play in the unfolding events? How does his character evolve throughout the story?

6. How do Lucy Barton and Olive Kitteridge’s meetups reveal different aspects of their personalities? If you could ask either character any question, what would you ask?

7. What does the novel suggest about the nature of love and its various forms?

8. How do the characters grapple with the question “What does anyone’s life mean?” What are some examples of this?

9. Discuss the idea of “unrecorded lives” as presented by Olive Kitteridge. How does this concept resonate throughout the novel? What does this concept mean for you?

10. How does the author use silence and what is left unsaid to convey deeper meanings and emotions?

11. How does Strout use the theme of friendship to explore the complexities of human relationships?

12. In what ways do the characters seek to leave a mark on the world, and how successful are they in their endeavors?

13. How did this novel make you think about your own legacy?

14. How does the novel address the theme of healing and redemption? Which characters experience the most significant transformations?

15. If you’ve read other books by Elizabeth Strout, what was it like for you to see the characters’ universes converge? Which characters were you most eager to see again?