Spoiler Warning: These book club discussion questions reveal important details about Olive Kitteridge. Finish the book before reading on.
- Did you feel sympathy for Olive by the end of the novel? Did you like her?
- In "Pharmacy," why do you think Henry was drawn to Denise? Do you think he is right to feel guilty about his relationship with her?
- What are some of the themes about love and marriage that reappear in many of the stories?
- At the end of "The Piano Player," it says, "Angie...felt she had figured something out too late, and that must be the way of life, to get something figured out when it was too late" (60). What did Angie figure out? How does this theme of figuring things out too late resonate through other stories in the collection?
- Describe Olive's relationship with Christopher. Do you have sympathy for her as a mother? How would you describe her love for him?
- Why do you think it gave Olive "a little burst" to write on Suzanne's clothes and steal her shoe? Did you understand the concept of "little bursts?" What do you do to move you through life in the everyday?
- In "Starving," do you think Harmon ever left his wife? Do you think he is justified in leaving her?
- In "A Different Road," why do you think the things Henry and Olive said during the hostage situation were more traumatic than the violence of the situation itself?
- In "Winter Concert," Bob Houlton seems to love his wife despite his past infidelity? Do you understand why they stay together? Do you think people can commit infidelity even when they love their spouse? Could you forgive such a thing?
- Why do you think Olive visited Louise Larkin in "Tulips?"
- In "Basket of Trips," Olive thinks at the end that everyone has their own "basket of trips." Do you think this is true? Are these little lies people make in order to get by or is it an example of hope?
- Why do you think "Ship in a Bottle" has that title? What does it symbolize?
- In "Security," why does the butterscotch make Olive so mad? Does she overreact?
- Where is Rebecca going at the end of "Criminal?"
- Does "River" provide a glimmer of hope at the end of the novel?

