Warning: May contain spoilers
1. In Dear Money, how is art juxtaposed with commerce? What are the similarities and differences between bond trading and writing novels? India and her husband are both artists; how do their paths diverge and what does that say about each of them?
2. Who are Will and Emma Chapman, and how do their roles evolve over the course of the book?
3. What does "keeping up with the Joneses" mean to India Palmer? In what ways might Will and Emma have felt that India and Theodor were "the Joneses"? How does this type of aspiration or competition affect friendship?
4. Why does Win take India on as his protégé? Discuss the relationship between Win and his boss, Ralph Radalpieno—what has money done to them? What kind of competition are they involved in, and what do they get out of it?
5. Dear Money reflects on the drive in our society to have more. Is this an accurate portrayal? Does anyone feel that they have enough in this story? Who seems to be the most satisfied with his or her life?
6. What does the house at Pond Point symbolize for the couples in the book—Emma and Will, India and Theodor? In what way is the Maine house a metaphor for India's career?
7. What would you be willing to sacrifice to have more money? How do you measure success? India Palmer was a wife, mother, teacher, and an award-winning novelist before she decided to become a bond trader. Did she consider herself a success?
8. Is Theodor's assessment of India on page 235 accurate? "You're an artist. No matter what you do, you'll always be an artist. You can't turn your back on who you are by nature." How is India an artist at her core? Is being a top bond trader a creative art?
9. Explore India's transformation. What were her motivations? What are the consequences of her path to more money? Think about George Bernard Shaw's Pygmalion, and Lerner and Loewe's My Fair Lady, and other tales of transformation you might be familiar with. How is India's development different from or similar to Eliza Doolittle's and others'?
10. The novel is set during the heady days of 2007, when there seemed to be no end to the money that could be made and few foresaw the financial crisis closing in. What do you think happens to India after the book's conclusion? What do we know as readers that India can't possibly conceive, and how does that knowledge affect your reading of the ending?
11. It is perhaps not an uncommon dream to wish for a different career or more money or a nicer house, but few people take such drastic steps to achieve that dream. What alternate life do you dream about? Do you think there could be a benefit to dreaming about something you know will never actually happen, or if not, what would you be willing to sacrifice to make that dream come true?
12. The novelist Joseph O'Neill calls Dear Money "a skilled, always gripping satire of our foolish age." In what ways is the book a satire? And how have we been foolish in—and blind to—our material pursuits?