Pineapple Street

1. General Impressions

Gather initial thoughts and broad opinions about the book.

• The book features plotlines about all the Stockton children. Which ones were your favorite and least favorite?
• This book was published in 2023, and the early 2020s saw a huge rise in media that satirizes the hyper-wealthy. This includes television shows like White Lotus and Succession, films like the Knives Out series and The Menu, and books like The Atlas Six and Doorman Wanted. How does this book compare with others, not only in its genre, but also across different types of media?

2. Personal Reflection and Connection

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

• Between the entire Stockton family and their significant others, this book features a large cast of characters. Who do you identify with most and why?
• In your opinion, what are the positive and negative effects on someone’s life when they have extreme inherited wealth?
• How do you feel about how the Stockton family uses their money and privilege? Does your opinion of them change as the book progresses?
• This novel supports the adage “money can’t buy happiness.” How does this novel relate to this adage, and outside of the novel, what do you think about the veracity of this adage?
• Sasha is put in a situation in which she feels drastically out of place because of her economic and social standing. Have you ever been put in a similar situation? What did you do in this situation?

3. Societal and Cultural Context

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

• In the novel, how does the concept of generational wealth intersect with larger social and cultural structures and inequities, like sexism and racism? Why are these matters interrelated, and how do their intersections affect the characters?
• This novel portrays a cast of hyper-wealthy characters who begin to critically assess their own wealth and privilege and who start—to different degrees—altering their behavior to become more ethical and compassionate. This contrasts with classic novels about New York’s hyper-wealthy class. For instance, in The Great Gatsby, Nick Carraway decides that both the new and old money are decadent, corrupt, and ultimately irredeemable. In The Catcher in the Rye, Holden Caulfield infamously and derisively calls his materialistic and consumerist bourgeoisie peers “phonies.” Taking the temporal settings of the novel into consideration, why does Pineapple Street deviate from these classic formulas by redeeming the Stocktons (to a degree)?

4. Literary Analysis

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

• What is the significance of the Stockton house? Think about this question as capaciously as possible: for instance, in terms of larger social and cultural structures, in terms of setting, in terms of symbolism, etc.
• Why is this novel told primarily from the point of view of the protagonist Sasha, an outsider to the Stocktons’ world? How would the story change if an insider told it?
• Discuss the character arcs of the novel’s main characters. Who changes the most and least? What does this change or lack of change signify about their character and society more largely?
• At the beginning of the novel, what does money symbolize? As the characters grow and change, how does the idea of money as a signifying force also change?
• Why is it important that this story is set in New York City? How does this setting affect the characters, themes, and plot? How would the novel change if it were set in a different American city?

5. Creative Engagement

Encourage imaginative and creative connections to the book.

• When converting novels to film—particularly novels that concern the hyper-wealthy—the choice of director and main cast can affect a movie drastically. For instance, director Jon M. Chu’s stylized, on-location set pieces and immersion in stories about heritage and family characterize his adaptation of Crazy Rich Asians, while director Baz Lurhman’s heightened theatricality and vibrant, colorful visuals characterize his adaptation of The Great Gatsby. Who would you choose to direct a film adaptation of Pineapple Street? Who would you assign to the main cast?
• Complete a short creative exercise where you rewrite part of the story through the lens of a different child in the Stockton family or their significant other. Is your narrator unreliable? Do they tell the story differently? After this exercise, share how this new perspective changed the story, and why these changes are meaningful.

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