1. In the first chapter, Meg must decide whether or not she can leave her family for a few days to go on a business trip to London. How does Meg’s identity as a mother and wife conflict with her career? Do you think she settled?

2. Kit, Sarah, and Meg are all in romantic relationships that make them unhappy, yet they can’t leave. Is this a common, universal situation? What are some other universal feelings like the fear of loneliness and need for security focused on in the novel that everyone can relate to?

3. Which Brennan sister do you relate to most, and why? What makes all these women similar? What makes them different?

4. As a teenager, Meg was babysitting when she delegated responsibility to Brianna, who turned her back and almost let a little girl drown in the family pool. In what way did that incident affect Meg’s relationships with her sisters? What about her relationship with her dad?

5. Meg’s sisters call her the rock of the family, nicknaming her “Sister Mary Margaret.” What kind of pressure does this put her under, both in the present and as they were growing up? Does she come to embrace that identity by the novel’s end?

6. Meg says, “If there’s anything she’d learned growing up in a big family, it’s that talking too much always led to trouble.” Describe the secrets the Brennans keep from each other, the secrets they gossip about amongst each other, and why.

7. Discuss the influence of religion and Catholicism in the story—including the role of guilt and shame as feelings often discussed in Meg’s narrative.

8. Describe how the different beautiful and scenic settings—the Napa Valley vineyards, London, the beach house in Capitola—influence Meg’s emotions and actions.

9. Meg doesn’t see herself as the confident, beautiful woman that Chad says he sees. Was Meg’s affair with Chad only physical? Is it possible he took advantage of her vulnerability, or do you believe Chad truly loved her?

10. Meg worked with Chad at the winery for years before starting the affair. In your mind, what was the turning point for her that started the affair? Does the author give us insight into this?

11. How is Meg’s love for Jack different than her love for Chad? How do those feelings change over time in each relationship?

12. How did Meg’s affair touch each person in her family—Jack, their kids, her sisters and parents?

13. Sarah and Boone’s relationship has never fully recovered from Boone’s affair. Meg says, “the seed of doubt had been planted. Sarah and Boone were together but Sarah was no longer secure.” Do you think Meg and Jack’s relationship will ever truly be repaired? Can a marriage ever truly recover from adultery?

14. Do you sympathize more with Jack or with Meg?

15. Jack’s side of the story isn’t revealed until the last chapter, when he has an honest conversation with Meg about their reconciliation in the kitchen. Does his defense and his apology change your view of Meg’s affair? Is only one person to blame, or do they share equal blame for the affair? Would you ever take back a cheating spouse?

16. In the beginning of the book, Meg’s sisters describe her as the dependable, responsible, bossy sister and even Meg says she is uptight and no fun. By the end of the story, has she changed? What does the last scene at the fair with Tessa and Gabi imply?

17. Meg believed that “good women were supposed to be strong and selfless.” What do you think makes a person “good”? Despite the affair, is Meg a good person? A good wife? A good mom, daughter, and sister?