Characters & Relationships

1. The story opens with Jill suggesting a road trip to reconnect with Jack. What were your first impressions of their marriage? How did these impressions change as the story progressed?

2. Discuss the significance of Jill's yoga practice and her carefully maintained appearance. How does this exterior reflect or contrast with her interior life?

3. Jack plans to start a new life at Shady Canyon with Erica. How do you think his relationship with Erica differs from his marriage to Jill? What draws him to each woman?

4. Pickleball serves as both a social setting and a battlefield in the novel. How does Jill's first meeting with Erica during pickleball lessons set the tone for their relationship? What does the sport reveal about each woman's character?

5. Discuss the symbolism of Jill and Erica meeting through pickleball. How does the competitive nature of the sport mirror their eventual conflict?

6. How does their daughter Maggie's departure for college affect Jill and Jack's relationship? How might their marriage have been different if she had stayed home?

Setting & Atmosphere

7. The story moves between the pickleball courts, affluent Laguna Beach, the Utah desert, and luxurious Shady Canyon. How do these locations reflect the characters' emotional journeys?

8. Discuss the significance of the golf resort, beach community and pickleball community settings. How do these exclusive recreational environments play into themes of appearance versus reality?

9. What role does the road trip setting play in revealing the truth about Jill and Jack's relationship? How does physical isolation affect their dynamics?

Themes & Motifs

10. The novel explores the idea that "some secrets keep a couple together." Discuss the various secrets in the book. Were any of them justified?

11. How does social status and the pressure to maintain appearances influence the characters' choices? Consider both the Laguna Beach and Shady Canyon settings.

12. Discuss the theme of control in the novel. How do different characters attempt to maintain or gain control? Who ultimately has the most power?

Plot & Structure

13. At what point did you begin to suspect the truth about Jill and Jack's past? What clues did the author provide?

14. Consider the road trip's trajectory. How does the physical journey mirror the psychological unraveling of the characters?

15. Discuss the significance of the ending at Shady Canyon. Was it satisfying? What alternatives might you have imagined?

Social Dynamics & Power

16. How does the pickleball community represent the larger social dynamics of the novel? Consider the relationships, rivalries and alliances formed on and off the court.

17. Discuss how recreational activities (pickleball, golf) serve as status symbols and social currency in the characters' world. How do these activities influence their relationships?

Deeper Analysis

18. How does the novel challenge or reinforce our assumptions about marriage, love and loyalty?

19. Consider the title "Jill Is Not Happy." How does its simplicity belie the complexity of Jill's character? What different meanings might it have?

20. How does the author use the contrast between wealthy coastal California and the desert to enhance the story's themes?