Gather initial thoughts and broad opinions about the book.

1. How did the novel’s shift from domestic drama to high-stakes thriller feel to you as a reader? Did the transition feel natural, or did one genre ultimately overshadow the other?

2. How did you react to the portrayal of the ultra-rich art world? Did it remind you of other novels that expose the hidden lives of wealthy communities, such as Liane Moriarty’s Big Little Lies (2014)? What similarities or differences stood out to you?

3. Did you find the conclusion to Clare’s story satisfying, and what did her final actions suggest about the person she had become?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Clare feels she has to wear a “mother mask” that erases her former identity. Have you ever felt the need to adopt a “mask” for a particular role in your life, whether in family or at work? How did that affect your sense of self?

2. What makes a shared passion, like the love of art between Clare and Gabriel, such a powerful force for connection? Think about a hobby or interest that is central to your own identity and how it shapes your relationships.

3. Jed hides significant truths from Clare, believing he is protecting her. In your own experience, can hiding difficult truths from a loved one ever be justified? Where do you draw the line between protection and deception?

4. What did you think of Clare’s final confrontation with her controlling mother-in-law, Dorothy? How have you navigated relationships with people who use passive-aggression or social standing to exert influence?

5. The story begins with a single lie that snowballs into a criminal conspiracy. Think about a time a seemingly small decision had much larger consequences than you anticipated. How does the novel capture that feeling of losing control?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The novel uses shell companies and sanctioned oligarchs to explore how immense wealth can shield people from the law. What does the book suggest about the relationship between money, power, and justice in our world today?

2. MoCA’s decision to deaccession Longfin is a key plot point based on a real controversy. How does learning about this real-world context change your perspective on the museum’s actions in the story?

3. How does the novel critique the specific pressures placed on women and mothers within affluent, high-society circles? What does Clare’s journey reveal about the conflict between societal expectations and a woman’s desire for an authentic life?

Dive into the book’s structure, characters, themes, and symbolism.

1. How did your understanding of Longfin change throughout the novel? At what point did it become more than just a valuable painting, and what do you think it ultimately represents within the story?

2. At what point did your theory about Gabriel’s murder change the most? Which clue—or which character—caused you to rethink what you thought you knew?

3. By the novel’s conclusion, did you still view Clare as the story’s hero? Why or why not? How does her transformation compare to other morally complex protagonists, such as Tom Ripley in Patricia Highsmith’s novels? 

4. Which character changed the most between their first appearance and the end of the novel? Did this have more to do with character development or simply the revelation of new information by the narrative? Discuss specific moments that caused you to reassess your opinion of this character.

5. Which plot twist or red herring did you find most effective in the story? Looking back, did Andrews provide enough clues for readers to solve the mystery before the final revelations, or did the solution rely more on surprise than deduction?

Encourage imaginative and creative connections to the book.

1. If The Fine Art of Lying were adapted into a television series, which actor would you cast as Clare, Jed, Gabriel, Tasha, and Dorothy? Which scene would you be the most excited to see brought to the screen and why?

2. Imagine you are curating a museum exhibition inspired by the novel. Which five works of art—real or fictional—would you include alongside Longfin? What themes or ideas would connect them?

3. Suppose the novel continued for one more chapter set five years later. Which character would you most want to revisit, and what do you think their life would look like after the events of the novel?