Book Club Discussion Questions for The Ice Cream Queen of Orchard Street by Susan J. Gilman

1. Lillian frequently attributes moments in her life to fate: her accident, her arrival in New York City the same year that continuous freezing was invented, et cetera. Do you believe it was fate? How does Lillian's assertion about fate "shaping" her destiny square with her story?
2. Do you like Lillian? Do you understand her? How do these two judgments differ? Would you say she's in any way the hero of the book?
3. Lillian's world broadens in almost unimaginable ways, from her fleeing the pogroms to heading an ice cream empire. Do you think this is a specifically American story—or could such radical change take place in another country?
4. At what point does Malka really become Lillian? Is it the baptism, when she changes her name? Earlier? Later? If you had the opportunity to take on a new name and identity, would you?
5. Rocco Dinello is Lillian's nemesis. Do you think he's the main villain in this story? Could you make a case for his actions? Do you sympathize with him at all?
6. How would you characterize Lillian's reactions to the surprises in her life—to Bert's lateness returning from gambling in Atlantic City, for example, or the shock of returning from her honeymoon to find herself out of a job thanks to the Cannoletti and Dinello merger? How are her reactions similar or dissimilar to her mother's responses to disappointment? Would you argue that Lillian is more like her mother or her father?
7. After Lillian sees that the Candie Ice Cream Company has been shut down, she expects to feel elated—but instead finds herself feeling "no satisfaction at all." Did you expect this?
8. How does Lillian's handicap affect her day-to-day life? Her overall story? Do you think it was a major obstacle—or a blessing in disguise?
9. Lillian is the driving force behind Dunkle's Ice Cream Company, but Bert is given the credit for starting, running, and expanding the company. The word "feminist" never crosses Lillian's lips, but do you think she'd call herself one? Why or why not?
10. Many of the characters in this book are tricksters at best, con artists at worst. Lillian and Bert begin their ice cream business by knowingly selling fake watches; Lillian's father kites checks and possibly recruits his children to perpetuate a scam. Is this trickery a family trait? Is there anything likable about it? Why do you think Lillian's schemes tend to work out and her father's tend not to?
11. Do you think Jason spends time with Lillian only because he's eyeing his inheritance, as Lillian once claims? How much do his motives matter?
12. Several points of conflict in the novel are ambiguous. For example, it is not made clear whether Bert is actually cheating on Lillian during their marriage—or whether the Dinello brothers are in fact helping to orchestrate the boycott against Dunkle's. What did you assume? Is it important to know one way or the other?
13. Toward the end of the book, Harvey Ballentine says, "Bad, good. Good, bad…Isn't that everyone?" Do you agree? Are all the characters in this novel both good and bad, or are they largely defined by one or the other?
14. Do you feel sorry for Lillian's son, Isaac? Why or why not?
15. By the end of the book, Lillian is wondering how the great, powerful nation she loved has become "small-minded and ingrown and frightened." Do you think her indictment of America rings true? Or is it her perceptions that have changed?
16. Lillian and Bert both arrive in America through Ellis Island, providing, as Lillian exclaims, less information and documentation than today's children are required to provide to enter preschool. How do you think Lillian's experience compares to the immigration experience today? What is the same? What is different? Have you ever moved to a new country? What difficulties did you experience? What opportunities did you find?
17. The Ice Cream Queen of Orchard Street spans seventy years. Did it illuminate any points in American history for you? What surprised you the most?
18. Author Susan Jane Gilman has often been celebrated for her humor. Did you find this to be a predominantly comic novel? Why or why not?

Unless otherwise stated, this discussion guide is reprinted with the permission of Grand Central Publishing. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.