1. “But the worst dream, the one that repeats, is that I sit down at the desk to write and there is the stack of letter writing paper, there are my pens, there are the envelopes, and I’m pawing at them like a cat, but I cannot pick them up...I can’t write.” Sybil states this early on in the narrative, about the dreams she is having as she deals with going blind. What did this tell you about her character early on?

2. Sybil is not only a fanatic for the art of letter writing, she holds classic forms of communication in high regard (she tells James that she still reads the newspaper “in print, adequately edited, without the muck of advertisements blinking away”). What value do you see in these older forms of communicating? Are there things you wish were still mainstream that have been replaced by modern tech?

3. Sybil often remarks in her letters that they are follow-ups to phone calls or in lieu of calls so that she can compose her thoughts. What, do you find, are the benefits of writing out thoughts instead of a call? How do you think it helps Sybil to deal with the strained relationships in her life?

4. Sybil doesn’t just communicate with her contemporaries but younger people as well, like Harry and the high school student writing a paper on her. How did you notice her tone shift when addressing these characters of various ages? How does Sybil paint a different picture of herself with different people? Which one is the “true” Sybil, if any?

5. Sybil writes to Joan Didion and Ann Patchett, among others. Which authors would you send letters to, whose work has impacted you the most?

6. During one of her letters to Harry, in answer to his question about her history, she briefly tells him and ends with “now that’s me breezing over something like 30 years of day-in-day-out work.” If you had to distill your professional history into a few sentences, what would you say?

7. Did you have any theories about who the unsent pages throughout the novel were intended for?

8. Sybil ends up in quite a love triangle. Between Theodore and Mick, who were you rooting for, if any, for her to wind up with?

9. Were you shocked at Rosalie’s “betrayal” with Sybil’s daughter? Did you see it as a betrayal, as Sybil calls it?

10. When Sybil reveals the truth about Gilbert’s death, how did this shift your understanding of her?