Pineapple Street

A deliciously funny, sharply observed debut of family, love, and class, this zeitgeisty novel follows three women in one wealthy Brooklyn clan

Darley, the eldest daughter in the well-connected old money Stockton family, followed her heart, trading her job and her inheritance for motherhood but giving up far too much in the process; Sasha, a middle-class New England girl, has married into the Brooklyn Heights family, and finds herself cast as the arriviste outsider; and Georgiana, the baby of the family, has fallen in love with someone she can’t have, and must decide what kind of person she wants to be.

Rife with the indulgent pleasures of life among New York’s one-percenters, Pineapple Street is a smart, escapist novel that sparkles with wit. Full of recognizable, loveable—if fallible—characters, it’s about the peculiar unknowability of someone else’s family, the miles between the haves and have-nots, and the insanity of first love—all wrapped in a story that is a sheer delight.

These book club discussion questions were provided by Penguin Random House.

Book club questions for Pineapple Street by Jenny Jackson

Use these discussion questions to guide your next book club meeting.

The Stockton family is both a typical and extremely unusual American family. Are there ways in which you relate to them, and others in which find them entirely unrelatable?

The novel is set in the small neighborhood of Brooklyn Heights, offering historical, architectural, and cultural details about the community. How does the setting shape the characters in this novel?

How would you characterize each sibling’s relationship with the generational wealth they were born into? Georgiana is the baby of the family, ten years younger than her siblings. Does Georgiana’s age alter her attitudes about wealth?

Brady claims to be in love with Georgiana. Do you believe him? Do you think his treatment of Georgiana was despicable, or were his intentions good?

Georgiana has two very different love interests, Brady and Curtis. Compare and contrast the two men. What does she get from each of them?

Darley left the workforce to raise her two children but feels deeply conflicted about her identity as a stay-at-home mom. Why does Darley’s background make this especially fraught for her? How does she have it easier than other parents?

Darley keeps Malcolm’s firing a secret from the Stocktons. Is this an act of love, or a betrayal of Malcolm—or both? Is Darley a good ally?

In the opening chapter, Sasha is mistaken for a server at the housewarming party, which makes her feel further out of place among her in-laws and their guests. At what other points in the novel is it made clear that Sasha is an outsider? Do you think Sasha will eventually gain an intuitive understanding of how the Stocktons dress and act? Could you change your instincts in a circumstance like that?

Sasha finally asks Cord to put her first, to put her needs before those of his family. Is she holding him accountable enough? Do you think Cord has been fair to Sasha?

What does Mullin represent for Sasha? What did she learn from that relationship? How did Mullin set her up to look for the wrong things in a marriage?

What does the house on Pineapple Street represent for the characters in this book? Does it have a different meaning to each of them?

Darley says she is an orange, Cord is a pineapple, and Georgiana is a cranberry. Which fruit would you characterize Sasha as? Which fruit would you be?

Pineapple Street Book Club Questions PDF

Click here for a printable PDF of the Pineapple Street discussion questions