1. Why does Cathie feel the need to start a women’s group? What crossroads has she arrived at in her life? How does her children moving away from home change the way she feels about her place in society?

2. Cathie and Denise become fast friends, but their relationship is far from smooth, even at the beginning. In what ways do their personalities clash? In what ways do they complement one another? Why do you think their complex relationship ends up being so special?

3. Why does Cathie retell the story of applying for food stamps when her children are young? What does that story tell the reader about Cathie’s life as a young mother? What do we learn about her background, and how does it inform the woman we meet in the memoir?

4. Discuss issues of ownership as they are portrayed in the memoir (Cathie’s need to own a house, and Denise’s need to own garage sale bargains). What does owning material objects mean to each of the women? How do their different backgrounds inform this need?

5. Denise and John have unique and unconventional marriage. How does Cathie feel about their relationship? Do you think she envies them, or pities them? What about the marriage works for Denise, and in what ways does the arrangement fail her? Do you think John and Denise are in love? Why or why not?

6. Cathie had very complicated, mixed feelings about Denise’s illness. In what ways does Cathie let Denise’s MS affect their friendship? Would you say that Cathie takes care of Denise when she is ill? In what ways does Denise’s MS frustrate and disappoint Cathie?

7. Discuss Cathie and Denise’s trip to Jamaica and Cuba. In what ways is the trip a turning point for both women? What do they each discover about themselves on the trip and what do they discover about one another?

8. Why does Cathie include the story of her visit to New York to see where Denise grew up? What does visiting Denise’s home, and meeting the women she grew up with tell us about Denise and her upbringing? Why does meeting these women have such a profound effect on Cathie?

9. Toward the end of the memoir, Cathie writes about her own mother, and the struggles she faced raising Cathie and her siblings. Is Cathie anything like her mother? In what ways does Cathie escape her families’ legacy? In what ways does she continue where her mother left off? How does her family and her childhood haunt her into her adult life?

10. In the end, Cathie and Denise have a falling out and Cathie does not attend her friend’s memorial service. Do you think Denise orchestrated their rift to protect Cathie, as Cathie assumes? Do you think Cathie can really find closure?

11. Cheap Cabernet follows in a tradition of many great memoirs, novels, and movies about women’s friendships. How does this book fit in to that tradition? How is Cathie and Denise’s friendship unique from others you have read about or seen?