1. Why do you think it took Anderson and Gloria so long to have this kind of discussion? Does old age provide a kind of urgency for these conversations? Have you had a similar dialogue with a parent or grandparent?

2. Gloria writes, “My first reaction upon reaching ninety-one is surprise.” Have you had the same feeling upon reaching a milestone birthday? Do you think we feel frozen at a certain age? What age would that be for you?

3. Anderson writes that he assumed he wouldn’t live past 50, which is the age at which his father died. Is it hard for you to imagine living past the age at which a parent has died?

4. Great wealth can open many doors, but it can also be a burden. How does Gloria’s case illustrate this? Would you want to be wealthy beyond all imagining? Like Gloria, do you think you would reject the idea of sitting on a beach somewhere, or not?

5. The novelist Mary Gordon wrote, “A fatherless girl thinks all things possible and nothing safe,” a line that has resonated with Gloria throughout her life. Do you think this is true? How does it apply to Gloria’s decisions about romance, career and family?

6. Anderson and Gloria learn in the book that they had each fantasized about being left a letter by their deceased fathers. Have you ever imagined the same kind of letter from someone you loved and lost?

7. In what ways does Anderson take after his mother? What do you see as their most striking differences?

8. Do you believe that everything happens for a reason, as Gloria does, or do you reject the concept, like Anderson does? Why?

9. Do you tend to plan for the future, as Anderson does, or assume that things will work out, in his mother’s style?

10. Toward the end of the book, Gloria writes a letter to her 17-year-old self. If you were to write a letter to yourself at 17, what would you say?

11. What do you think of the phrase, “The Rainbow Comes and Goes”? How does it apply to the authors’ lives? Does it apply to your own life, too, and if so, how?