1. Why do you think the novel is titled "The Season of Lillian Dawes"? What are some of the various meanings for the word season, and how do they pertain to this story?

2. Why did Mosby tell the story through Gabriel, instead of through Lillian or even Spencer? Is he a reliable narrator? Is he, as his name suggests, a "bearer of truth?"

3. Lavinia tells Gabriel, "I've never made a fetish of the truth, my dear . . .. The truth is overrated. It's the refuge of the dull and unimaginative and most of the time it's a big disappointment, while a lie worth telling or well told is, well, a kind of gift." How does this statement apply to Lillian? To Spencer? To Gabriel? How important is the truth to you?

4. Having taken on the role of Gabriel's guardian, Spencer also takes responsibility for his younger brother's education as well as his moral development. Is Spencer a good role model for Gabriel? Is his "bohemian" lifestyle appropriate for a teenager?

5. Why do you think Gabriel is so drawn to Lillian, even before he meets her?

6. After learning about archetypes from Spencer, Gabriel starts to regard all the women he encounters in classical terms, identifying Hadley, for instance, as a witch. The only woman he can't classify is Lillian. Why is that? Does Gabriel's infatuation with Lillian cloud his judgment? Or is she truly extraordinary and beyond classification?

7. Like Lillian, Spencer is the kind of person who draws people to him; they are fascinated with him and seem to like him without even knowing him. What makes him so likeable? If you met Spencer do you think you, too, would be charmed by him?

8. Lillian, it turns out, is a master of trompe l'oiel painting, a style that depicts objects with photographic detail, and which is often used as a transformative method of interior decorating. Why is it significant that Lillian would develop a talent for this kind of artistic expression?

9. After Lillian leaves Clayton's house, Gabriel discovers a scrap of paper on which she has written the words Schadenfreude and Weltschmerz, German terms that have found their way into the English lexicon. Discuss the meanings of these words. What do they mean to Lillian? How do they foreshadow other events in the novel?

10. In Lillian, Aunt Lavinia recognizes a kindred spirit and strives to protect her. Why is this, and why doesn't she reveal Lillian's secret to Spencer and Gabriel?

11. Spencer tells Gabriel that "It is a feature of modernity to be handicapped not by our abilities to do, but by our abilities to see, in the grand sense that renders the fulfillment of meaning. Hence the frustration that leads to decadence, paralysis, and futility." He also says that the cure for this "modern condition" is literature and love. Discuss this passage and its meaning for Gabriel, Lillian, and Spencer. Who of these characters would you characterize as "modern?" And how are each of their lives affected by literature and love?

12. Mosby's characters spend time in venerable Manhattan icons: the Plaza Hotel, Rumpelmeyers, Central Park, even checker cabs. How is New York, a city that Spencer says will "break your heart a thousand times a day," a character in the novel?

13. Discuss the epigraph, a quote from Flaubert. How is it appropriate for this novel?

14. Why does Gabriel, in the novel's first paragraph, describe himself as a witness to a tragedy? What was the tragedy, and whom did it involve?