1. Tad Friend opens his memoir with a scene in which his father, Dorie, is documenting the family house, which the author’s late mother, Elizabeth, had perfected in her own way. Why do you think Friend chose to open his memoir with this scene? How does this scene resonate through the rest of the book?

2. Friend notes on page 9 that his four grandparents constitute a Wasp compass: loquacious and madcap; brainy; haughty; moneyed and timid. Which of these four sets of characteristics seems most universal among Wasps? Which compass point does Friend himself seem to pursue?

3. Friend suggests that Wasps are defined less by skin tone and religion than by a certain cast of mind (page 12). How would you define that cast of mind?

4. In what ways does Tad Friend himself seem like a true Wasp? In what ways not?

5. What do you make of the Wasp affinity for mud that Friend details in chapter 2?

6. Friend’s relationship with his parents is sometimes problematic. How has their family dynamic been shaped by their broader heritage? What part of the Friend family dynamic seems to you typical of all families? What part seems peculiar to Wasps?

7. The book’s title is taken from a ritual from Friend’s childhood, in which good humor under duress or spontaneous helpfulness among the children was rewarded with a quarter. How might you relate this practice with other themes of the book?

8. When Tad Friend was in his twenties, he lived a fastpaced life in New York and fell in love with Giovanna Visconti --- a period he calls “the most hopeful chapter of my life” (page 116). Why do you suppose Friend considers this chapter his most hopeful?

9. Which Wasp characteristics do you most admire? Which would you rather not experience firsthand?

10. Near the end of the book, Tad Friend’s father takes issue with Tad’s portrayal of his mother. Do any other issues seem to underlie their confrontation?

11. By Friend’s own admission, he spent most of his inheritance on two decades of therapy. How might “the talking cure” have worked to alleviate some of the personal and cultural attributes that Tad was trying to leave behind?

12. In some ways, Cheerful Money is a record of the decline and fall of the Wasps. Given the course of American history, do you think this decline was inevitable? How would you compare the Wasps to other American tribes?

13. In what sense is it signifi cant that the key to the Friend family mausoleum has been lost (page 343)?

14. Which Wasp traits and traditions do you think are here to stay?