1. Why is this novel called “The Lost Art of Gratitude”? Who is, or should be, grateful? Why is it a lost art?
2. One of Isabel’s guiding principles is “moral proximity”: If someone you know is in trouble, you must try to help—a notion that Jamie seems to consider meddling. In what ways does this make Isabel’s life more fulfilling? And more difficult? What do you think Isabel gets out of this?
3. On page 15, Isabel muses about her life: “She used to think that her major achievement in life had been the editing of the Review, or perhaps her doctorate; she no longer thought so—now she felt that the most important thing she had done was to give birth to a whole new life, a whole new set of possibilities.” What does this say about her as a philosopher? As a mother?
4. “Perfect villains have to live somewhere, and even the most innocent-looking suburb can conceal its surprises” (p. 21). How does this notion play out over the course of the novel? Is there a perfect villain within Isabel’s circle?
5. What role does money play in the novel? How does Minty’s wealth affect the way Isabel deals with her? Are there other instances in which money affects characters’ behavior?
6. “Stoicism and defeatism, of course, can be kissing cousins, but Isabel would never find fault in Jamie’s quite exceptional ability to accept setbacks” (p. 47). What does this tell us about Isabel and Jamie’s relationship? How does Isabel respond to setbacks? Is this a function of the difference in their ages?
7. Isabel thinks quite a bit about Scotland, almost as if it were a character in its own right. What point is Alexander McCall Smith trying to make?
8. “Yes, she thought, our very ordinary freedoms were being rapidly eroded by the nanny state, but it was difficult to make the point without sounding strident, or like an opponent of motherhood and apple pie. So she had done nothing to defend these freedoms, which made her . . . the realisation was a shocking one: it made her one of Christopher Dove’s free riders” (p. 101). How does the notion of free riders play into the larger plot of the novel? Who else is accepting a free ride, and how?
9. Discuss the plagiarism subplot. What purpose does it serve? What does Isabel’s handling of the situation tell us about her character?
10. Two of Isabel’s acquaintances refer to Minty as “wicked” (p. 181). Do you agree with that assessment? Ultimately, does Isabel?
11. Given the way Isabel dispatched Christopher Dove and Professor Lettuce, what do you think about the suggestion that she is an “enforcer” who “specialised in ruining reputations” (p. 195)? Would Isabel concede that there is symmetry between the plagiarism episode and the Minty/Jock affair?
12. On page 252, Isabel explains the liar paradox, and ends by reassuring Minty that she won’t divulge her secret. What point is she trying to make? Why does Isabel choose to keep her word to someone who has told so many lies?
13. Discuss Isabel’s relationship with Cat. How does Isabel treat her niece? What does she expect from her?
14. Reread the song lyrics on page 261. How do they reflect upon the events of the novel? What does the song say about Jamie’s feelings toward Isabel?
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