1. Natalie's story is interwoven throughout the novel in the form of recollections -- memories that later come into question when her children read her story. Discuss the power of personal memories; how can they vary so drastically from one family member to another? Can you always trust your memories -- or do we all revise and alter our memories one way or another?

2. Which qualities make Olivia a good person to help Natalie write her memoirs? Her natural curiosity? Her fascination with the intricacies of family dynamics? Does the absence of Olivia's own family history help or hinder this process?

3. At first, Tess and Simon find themselves at odds with one another. Is this because Tess reminds Simon of the daughter he lost? Does Tess sense and subsequently feel threatened by the growing attraction between Olivia and Simon? Are Tess and Simon more alike then different -- outsiders in a world filled with people who do not understand their pain?

4. How is Olivia affected by her realization that the Seebrings aren't the perfect family she envisioned? Is Olivia disappointed by the choices Natalie made to save the vineyard? How practical were Olivia's expectations when she arrived at the vineyard? Is she realistic when she hopes that the Seebrings might become a pseudo-family?

5. Natalie and Olivia discuss the legitimacy of the expression "blood is thicker than water." (ms. p. 273) Do you agree or disagree with this sentiment? Is it possible to forge a family-like bond with friends when one does not have a family of their own? In the end, are family bonds stronger because they are permanent and enduring -- or does the process of choosing to be close to someone strengthen the bonds of friendship?

6. Discuss Natalie and Carl's lifelong love affair, and their ability to set aside their feelings for almost sixty years. Does their shared love for the vineyard exceed even their feelings for one another? Did the fact that they were able to live their lives side by side -- if only as employee/employer rather than husband and wife -- make their choice easier or harder?

7. Discuss the importance of the vineyard as a lifeline between everyone associated with the winery. Who loves the vineyard the most? Discuss how the vineyard becomes a character in its own right: its changing moods and its need to be loved and cared for if it's to thrive. Did the detailed information about grape growing for wine add to the pleasure of your reading experience?

8. Who paid the ultimate price for Natalie and Alexander's "marriage-of-convenience?" Natalie and Carl, who had to give up their love to save Asquonset? Alexander, who spent his life married to someone whose heart was taken by another? Greg and Susanne, whose needs were often overlooked for the sake of the winery?

9. Compare Natalie to Olivia's own absentee mother, and how each mother's parenting style affected her children. Which is more painful: having a mother who is physically present in one's life, yet emotionally remote, or having a mother who disappears altogether? Is Olivia's discovery of her mother's death tragic or liberating for her?

10. The major turning point in Simon's relationship with Olivia and Tess occurs when Buck gives birth to her kittens. Does this birth symbolize Simon's rebirth as a man, and his renewed hope for the future? Why is his first instinct to share this event with Olivia and Tess?

11. Discuss the role of women in The Vineyard. How did Natalie's gender affect the course of her life and the decisions she made? How did being a women help her? Did it make her life easier or more difficult? Would Natalie have been as happy if she'd also been the face of the vineyard as well as its brains and backbone, or was that job better left to Alexander?

12. Do you agree with Natalie's decision to keep Brad's true parentage a secret? How would the course of Natalie and Carl's lives have changed had Carl known all along that he was Brad's true father?

13. Carl and Simon enjoy an enduring, if quiet, bond as father and son. Did you want them to be more demonstrative toward one another, or does their relationship suit their personalities? How do you think their relationship was affected by the loss of their wives in the sailing accident?

14. Discuss Olivia's reaction to the death of her mother. Were you surprised by her relative composure, or did you expect a more volatile response? How did having the Seebring women near her for comfort affect Olivia's reaction? What did the blank diary owned by Olivia's mother symbolize?

15. Discuss the power of viewing history through the eyes of someone who lived it. How are personal memoirs different from straight historical accounts? Which ones are more accurate? Which ones are more interesting?