Book Club Discussion Questions
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Please be aware that this discussion guide will contain spoilers!
1. How do Lillian's feelings regarding her mother compare to her feelings regarding her Aunt Sadie Box sh? And how do these relationships shape Lillian's ambitions and sense of self?
2. What initially attracts Lillian to poetry and how does it remain signi cant throughout her life and career, in advertising and otherwise?
3. Why are Lillian and her son Gian's reactions to the Subway Vigilante and his crime so different? Why does Lillian love New York City unconditionally whereas Gian has come to fear it?
4. Have you ever loved a city or a place so much that you never wanted to leave it? Describe, saying where and why, or why not.
5. Why are manners and kindness so important to Lillian? How does civility relate to empathy and even to democracy?
6. How do Lillian's achievements and struggles at the of ce at Macy's—with her boss, Chester; with getting paid as much as her male colleagues; with her friend and rival coworkers, Helen McGoldrick and Olive Dodd—relate to the workplace as we know it today?
7. Why does Artie, Lillian's editor, want to change the title of her debut poetry collection from Oh, Do Not Ask for Promises to Frequent Wishing on the Gracious Moon? And why does she refuse? Do you think he was right or wrong, and were you pleased or disappointed when she said no? Explain why.
8. In what ways does walking in the city feed Lillian's poetry, her advertising work, and her curiosity? How does her relationship to walking change over time, as both she and her city get older?
9. Why is Lillian ambivalent toward motherhood, and how does her friendship with Wendy differ from her relationship with her son Gian?
10. Why, after scof ng at love and convention for so long, does Lillian fall so hard for Max? What is it about Max that she finds so irresistible?
11. Were you surprised by all the chance encounters that Lillian has with different people on her walk through the city? Why or why not? Do you also like to strike up conversations with strangers? Why or why not?
12. How worried, if at all, did you feel about Lillian as she made her way across Manhattan? Were you troubled by any of her encounters? Heartened? Both? Which ones and why?
13. Lillian can't stand the new and ugly Penn Station, built in 1968, that replaced the old and beautiful original — are there structures in your past that were torn down that you miss, too? Describe.
Unless otherwise stated, this discussion guide is reprinted with the permission of Picador.
Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.
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