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- Both Kerrie (Olivia) and Jordan (Jordana) assume new, invented identities to move on from their pasts. Discuss each woman’s reasoning for assuming a new identity and how these reasons are similar or different.
- Early in the book, Kerrie shares something her Nana used to say: “Senseless revenge will whip its neck and snap you on the bottom.” Discuss the different revenge plots in the novel. Do you think Kerrie’s reasons for revenge against Jordana are sensible? By the novel’s end, do you think she succeeds in her revenge?
- As part of their work in the marriage concierge business, Jordana and Kerrie see their fair share of different relationships and arrangements. Describe what marriage and love look like in their industry. Of the couples and marriages represented, do any seem happy or healthy to you? Which ones? Why or why not?
- Financial security is a major motive for Jordana, which is juxtaposed with her role in serving clients for whom money is no object. Discuss the different levels of wealth among the characters. Do you agree with Jordana’s determination for financial security? Why or why not?
- Jordana says that “happiness isn’t always a choice.” Do you agree with this sentiment? Why or why not?
- As a group, discuss what a marriage means to you. If you are married, what defines your relationship with your partner? Do you have an overbearing mother/mother-in-law like Caroline? When planning your wedding, did you find yourself anxious over everything like Alexa? If you are not yet married, describe the relationship you hope to be in and what you value in a partner.
- When Kerrie comes clean and admits her reasons for being in New York to Sara, the two devise a plan. Discuss Sara’s willingness to be involved and her desire to return to work. Can you relate to her trouble finding work in her early years of motherhood? Has anyone in your book group taken time off to build or care for their family? Consider the pros and cons of giving up work to become a stay-at-home parent and vice versa.
- Further to the above, mothers and motherhood are represented in many forms in Pretty Revenge. As a group, compare and contrast the different family dynamics and relationships that exist. Is Caroline similar to Sara? Is Jordana’s mother similar to Caroline? Discuss how the characters view their parents or the act of parenting.
- Kerrie’s past with Jordana is finally revealed in Chapter 26. Are you surprised by what happened between them? Do you think Jordana is responsible for Kerrie’s grandmother’s death? Why or why not?
- Considering the dual nature of decisions and their impact, there are always two sides to every story and every memory. What do you think about Jordana’s decision to take the ring and money? Do you think Kerrie would have seen things differently if she were older, and if her grandmother had survived?
- Why do you think Jordana’s mother is so insistent on having her reunite with her father? Do you think Jordana is right to want to avoid it? Are you surprised when Jordana and her mother reconnect in the final scene?
- At the end of your discussion, consider Pretty Revenge in the context of other popular female-driven thrillers, like Gone Girl by Gillian Flynn and An Anonymous Girl by Greer Hendricks and Sarah Pekkanen.