1. The voice of The Improbability of Love shifts between sections. How does the oscillation between the removed third-person narrative and the “voice” of the painting contribute to the narrative progress? What does the painting’s voice reveal to readers? How would you characterize “him”?
2. The Improbability of Love provides readers with a glimpse into the high-stakes world of the art-buying market. How would you characterize the business? Discuss the tension between art for collectors (or capital gains) versus art for public consumption as explored within the novel.
3. How would you describe Annie’s personality in the beginning of The Improbability of Love? How does it shift over the course of the novel? When does she demonstrate the most self-confidence?
4. Deception and secrecy are found throughout the plotlines of The Improbability of Love. Which characters use deception to get ahead? Which people demonstrate the most authentic version of themselves to the world? Which secrets are most surprising?
5. Intrinsic to the discussion of the art market is the relationship between commerce and beauty. How is this relationship explored in the novel? For whom does art exist? What does the sudden public interest in The Improbability of Loveassert about trendiness in art?
6. Viewing a painting is a highly subjective experience, informed both by emotion and intellect. What initially attracted Annie to The Improbability of Love? How does her perception of the painting change over the course of the novel?
7. Discuss the various players who are vying after the painting and their intentions behind purchasing it. Whose intentions—if any—are pure? Whose motivations are capitalistic?
8. The dinner party scenes within the novel describe a world of unfettered lavishness. How do these scenes contrast with Annie’s day-to-day life? Did you find any of the meals appealing? Discuss the concepts of “consumption” and “excess” as described throughout The Improbability of Love.
9. How would you characterize Annie’s relationship with her mother? What information about their shared history helped shape your understanding of Annie’s views on love?
10. The “voice” of the painting provides important historical and aesthetic context throughout the novel. Trace the history of ownership for The Improbability of Love. What struck you about the painting’s provenance? Why do you think the author chose to utilize this unique stylistic choice?
11. Discuss the role of Barty in the novel and his service of shaping the social elite. How is he received by his clients, particularly the Russian oligarch? What are his “rules” for making a grand entrance into high society?
12. Discuss the exclusivity of the art world in relation to class. How does the acquisition of art translate into power for various characters within the novel? Describe how Watteau’s impoverished history is contrasted with the multi-million-dollar frenzy surrounding his painting.
13. How does Annie’s view toward love change over the course of the novel? Describe her initial meetings with Jesse. When do her feelings toward him begin to shift?
14. Discuss Rebecca’s role in the art world and in her father’s business. How would you characterize her professional persona versus her personal one? When is she most powerful? Describe her moral dilemma when she finds out the truth about her father.
15. Memling’s life story is inspired by Nazi art thieves and the horrors of the Holocaust. Are there some parallels between Memling and historical figures?
16. How familiar were you with the art world before reading this novel? Did your perception of the business change or shift throughout the reading experience? Can you recall any particular works of art, exhibits, or performance pieces that elicited the same sort of frenzy described around Watteau’s work in the novel?