SPOILER WARNING: These book discussion questions are highly detailed and will ruin plot points, if you have not read the book.
Title: Olive Kitteridge
Author: Elizabeth Strout
Page Count: 286
Tone: Leisurely, haunting, character-driven
1. Olive Kitteridge is built from stories that jump through time to different characters’ points of view. What do you think of the “novel in stories” structure? Was it easy or hard to fall into the rhythm of this book? Would you have enjoyed this collection of stories more if it were a traditionally structured novel?
2. What is the difference between a novel in stories and a book of short stories?
3. How often did Olive Kitteridge appear in this book? Do you think she should have made fewer or more appearances?
4. Were there any stories you absolutely loved? What about stories that you disliked? Was there a story that you thought didn’t fit in the collection?
5. Olive Kitteridge won a Pulitzer Prize. Does the fact that Olive Kitteridge won a Pulitzer Prize make you feel the need to like it? Would your experience with this book make you want to read more literary prize winners?
6. Do you think “Pharmacy” was a good opening story for the book? Why do you think Strout picked it as the opener? Would you have started the collection with a different story?
7. In “A Different Road” Henry and Olive get held up by drug addicts in a hospital. Did you think this story fit in with the others? Was it too “overboard”?
8. What keeps Olive and Henry together over the years? Is there anything that almost tears them apart?
9. What specific moments make you like Olive? What specific moments make you dislike her?
10. Why did Olive steal and destroy some of Dr. Sue’s clothes during “A Little Burst”? Did you see any similarities between Olive and Sue? Did Olive’s behavior to Dr. Sue change your opinion of Olive? Why do you think Olive hates Dr. Sue so much?
11. Olive hears Dr. Sue and friends talking down about her at the wedding, why doesn’t she respond from her secret hiding place?
12. Why do you think Olive never committed suicide? First when her father died, next when Jim O’Casey died, finally when Henry died.
13. Why do you think Olive responds so fully to Nina in “Starving”?
14. In “Starving”, how did Harmon and Daisy go from casual sex to falling in love? Why do you think Harmon won’t immediately leave his wife? Do you think he’ll ever get divorced?
15. Why does Olive go to visit Louise Larker in “Tulips”?
16. In the story “Ship in a Bottle” Anita threatens to disown her daughter, Julie, if she lives with her boyfriend rather than marrying him. Is there ever a reason to disown a child? What about if you were in Louise Larkin’s position in the story “Tulips”?
17. In “Piano Player” Simon comes back to see Angie. Why does he bring up an awful memory about Angie’s mother coming to visit him?
18. In the story “Security” Olive goes to visit her son in New York City. Do you think Olive liked Christopher’s new wife, Ann? Would you have liked Ann?
19. Also in “Security,” what event caused Olive to want to leave Christopher’s home early? Did Olive choose to leave or did Christopher kick her out?
20. How does Olive view her relationship with Christopher? How does Christopher view his relationship with his mother? How do you think they came to be so disconnected?
21. Does your opinion of Christopher change, knowing that he only visited his father once in the nursing home, never called to check up on him and never offered to help his mother with the situation? What reasons do you think Christopher had for staying away from his parents?
22. Why did Strout include the story “Criminal”? Did you like the story – why or why not? How did it connect to Olive?
23. What is Olive’s relationship with Jack Kennison? Will their relationship last?
24. What does it say about Olive that not one time in her marriage did she ever say “sorry”?
25. Do you think Olive has changed by the end of the book? If so, how?
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