Lillian Boxfish Takes a Walk

Gather initial thoughts and broad opinions about the book.

1. In Lillian Boxfish Takes a Walk, the alternation between Lillian’s physical journey through Manhattan and her mental journey through memories creates a layered narrative experience. What elements of Rooney’s picaresque novel structure did you find most effective? 

2. Did knowing the novel is based on advertising pioneer Margaret Fishback affect your reading experience? If so, in what ways? Does this real-life connection remind you of other novels that blend fact and fiction, such as Paula McLain’s The Paris Wife, which fictionalizes Ernest Hemingway’s first marriage?

3. Lillian’s fierce loyalty to New York City despite its decline parallels her loyalty to her principles throughout her life. Does her perspective remind you of iconic New York narratives like E. B. White’s “Here Is New York” or Joan Didion’s “Goodbye to All That”?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Throughout her career, Lillian battles against gender-based wage inequality and limited professional opportunities for women. When have you encountered similar barriers in your life?

2. Lillian’s love for her son, Johnny, is profound yet complicated by her ambivalence toward motherhood and the way it changed her identity. What most struck you about this relationship? Did it remind you of relationships in your life?

3. Lillian prides herself on her “civility,” considering it her “true religion.” What role does civility play in your interactions with strangers? Do you find that genuine civility requires more effort in today’s world than in previous decades?

4. Which places from your past evoke strong emotions when you revisit them? How have those places changed over time, and has your relationship with them evolved in ways that mirror Lillian’s complex feelings about New York?

5. Lillian’s mink coat represents her independence and professional achievement in a world that often undervalues women’s work. What possession of yours symbolizes an important aspect of your identity?

6. At Wendy’s New Year’s Eve party, Lillian connects with younger generations despite feeling out of place. Have you experienced similar moments in which age differences both separated and united people in unexpected ways?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The evolution of women’s roles, from Lillian’s mother to Lillian herself to young Wendy, spans much of the 20th century. In what specific ways have opportunities and challenges for women continued to evolve since 1984?

2. Can you identify patterns in today’s culture in which innovations from marginalized communities become mainstream, similar to Lillian’s observations about jazz, the Lindy Hop, and rap music? What examples particularly resonate with you?

3. Advertising shifts dramatically over Lillian’s lifetime, from appealing to people’s rationality to targeting their anxieties. How would Lillian view today’s social media marketing and influencer culture?

Dive into the book’s structure, characters, themes, and symbolism.

1. Lillian’s advanced age and female perspective offer departures from the picaro role of the picaresque novel. In what other ways does Lillian both embody and subvert this typically young, male literary tradition?

2. The personification of the city and its neighborhoods creates a relationship between Lillian and New York that evolves throughout her life. What stylistic techniques does Rooney use to transform New York City from a mere setting into a dynamic character?

3. Which symbol in the novel—Phoebe Snow, the Oreos, the mink coat, or another—resonated most strongly with you? Why do you think Rooney chose these particular objects to represent thematic content about advertising, authenticity, and identity?

4. What is the effect of the alternating narrative structure between past and present? How would the novel’s impact differ if it were told chronologically rather than through the memories that Lillian’s walk triggers?

5. The motif of opposites runs throughout the novel—high versus low, civility versus incivility, progress versus decay. How do these binaries help illuminate Lillian’s character and her relationship with both advertising and New York City?

6. Lillian’s chance encounters demonstrate her genuine interest in people and her belief in civility even in a city many consider dangerous and declining. Of all Lillian’s interactions with strangers during her walk, which did you find most revealing or meaningful? Why?

Encourage imaginative and creative connections to the book.

1. Imagine that Lillian took a walk through your city or town today. What would catch her attention, positively or negatively, and how might she describe it in her characteristically witty, observant voice?

2. The novel concludes with Lillian trading her mink coat for Keith’s jacket, symbolizing an exchange between generations. If you could exchange a significant item with someone from a generation other than yours, what might you give and what might you like to receive? What would this exchange represent about the values of different eras?

3. Lillian created advertising copy that was clever and concise, appealing to intelligence rather than emotion. Draft a short advertisement for your favorite book, city, or product using Lillian’s professional philosophy.

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