Book Club KIT
“Vibrant and hilarious . . . brimming with truth.”
-Cynthia D’Aprix Sweeney, bestselling author of The Nest
About Pineapple Street
“A vibrant and hilarious debut . . . Pineapple Street is riveting, timely, hugely entertaining, and brimming with truth.”
—Cynthia D’ a prix Sweeney, New York Times bestselling author of The Nest
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 mother -hood 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.
Jenny Jackson is a vice president and executive editor at Alfred A. Knopf. A graduate of Williams College and the Columbia Publishing Course, she lives in Brooklyn Heights with her family. Pineapple Street is her first novel. #PineappleStreetDiscussion Questions
1. The Stockton family is both a typical and an extremely unusual American family. Are there ways in which you relate to them, and others in which you find them entirely unrelatable?
2. 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?
3. 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?
4. 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?
5. Georgiana has two very different love interests, Brady and Curtis. Compare and contrast the two men. What does she get from each of them?
6. 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?
7. 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?
8. 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?
9. 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?
10. 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?
11. What does the house on Pineapple Street represent for the characters in this book? Does it have a different meaning to each of them?
12. 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?
A conversation with Jenny Jackson
What inspired you to write Pineapple Street?
My little family of four spent much of the pandemic living with in-laws; my husband’s parents in Connecticut, and my parents in Massachusetts. It was amazing in ninety-nine ways—they helped with Zoom school and childcare, we had movie nights and long hikes in the woods—but it was also really funny to see how different our families of origin sometimes felt. I tease my in-laws about their plants (I think they must have two hundred plants in their house. They take pictures of them and call them their “grandbabies”), and I know my husband is mystified by my parents’ crazy art collection (They have tons of friends who are painters, and some of their art—like the stuff featuring naked people and cats—is pretty weird). So, I wanted to write about that funny feeling of being an outlaw among your in-laws, that feeling that no matter how long you are married you’ll never really get the plant thing or the naked-people-with-cats-art thing—you’re never really one of them.
You chose two unique epigraphs for Pineapple Street. One is from Truman Capote: “I live in Brooklyn. By choice.” And the other is from a New York Times article by Zoë Beery: “Millennials will be the recipients of the largest generational shift of assets in American history—the Great Wealth Transfer, as finance types call it. Tens of trillions of dollars are expected to pass between generations in just the next decade.” Can you explain the significance of each?
I love that Truman Capote quote because it foreshadows a really fun reveal late in the novel when Georgiana has to come face to face with her ingrained snobbism. But I also just wanted to point to the fact that while in some previous eras Brooklyn was seen as Manhattan’s inexpensive, frumpy little sister, that is just no longer the case. Where Sex in the City and Friends drew an entire generation of young transplants to Manhattan, Brooklyn is now more desirable. And then that second quote is from a piece that was hugely inspirational for me. Beery writes about rich millennial heirs who believe capitalism is a crime and that inherited wealth is intrinsically immoral. These young billionaires are trying to give away their fortunes, much to the chagrin of their families. It got me thinking about what it might feel like for those families to have to examine their own privilege, about who might be capable of change and who might really struggle to question their deeply entrenched views of money. Georgiana’s storyline grew from this article.
Each member of the wealthy Stockton family navigates their generational wealth in a different way. These differences reveal how personal our insecurities, guilt, and pride about money can be. When you created these characters, how did you develop their unique relationships to the family fortune?
Darley, the eldest, was born into money but gave up her inheritance when she married a successful Korean American investment banker and refused to have him sign the prenup, locking herself out of her trust fund. Darley is a romantic and she has always had some shame surrounding her wealth. Sasha is the outsider, a middle-class girl from New England who has married into the family, moved into their ancestral home, the limestone on Pineapple Street, but finds herself bewildered by the rites and rituals of the one percent. Sasha likes to think that she is immune to the allure of money, but that allure is insidious. And
Georgiana is the baby of the family, the Gen Z social conscience who grew up rich and spoiled and is suddenly seeing herself for the first time and questioning the morality of extreme wealth in a world with extreme poverty. I am very aware that Georgiana’s age means she has a really different attitude about money than the other characters. I am what we like to call a “geriatric millennial,” and so I wanted to explore the rift between people my age and people a decade younger.
When middle-class Sasha marries into the family, she becomes a keen observer of the Stocktons’ norms and rituals. How is the role of an in-law like the role of a novelist?
You know how when there is a gas leak in a house people who have been inside all day can’t really smell it, but then if someone walks in from outside the smell is overwhelming? I think the in-law is that person walking in from outside. They see things that are totally ingrained, that have developed over decades, total whack-a-doo behavior that has come to seem normal in a family. A novelist should operate in the same way, noticing everything, being both a part of the household but also seeing things with fresh eyes (or nose).
Though families from around the globe can relate to the challenges of navigating class and privilege—as well as navigating new in-laws!—Brooklyn Heights is where the Stocktons make their home. What are some of your favorite Brooklyn stories rendered on the page or screen? Did any of them influence Pineapple Street?
I love Andrew Sean Greer, Helen Fielding, Katherine Heiny, Jennifer Close, and Curtis Sittenfeld, but I have to admit that most of my comic inspiration comes from my friends and family. There’s a scene in the novel where the children carry around a dead pigeon in the park—my kids did that. There is a scene where a child swallows his aunt’s baby teeth and my friend’s child did that. From the dog who throws up the lacy underwear to the caddy appreciation day, much of the comedy here has been stolen from real life.
As an editor at Alfred A. Knopf, you’ve ushered in some of our most beloved novelists, including Kevin Kwan and Emily St. John Mandel. Was it always your ambition to write a novel of your own? What have you learned from transitioning from editor to author?
I really hadn’t planned on writing a novel, but I’ve learned so much from writing and editing this book, I wish I’d done it two decades ago. I feel like I understand structure in a new way; I understand the benefits and pitfalls of first-person versus thirdperson narration versus multiple points of view. Also, as an editor I used to do this thing where I would tell a writer, “Oh, why don’t you just try out the scene this way and if it doesn’t work we can scrap it.” Oh my God, that was heartless! I had no idea how painful it was to work on something for days and then throw it out! Kill your darlings feels like true murder.
What do you hope readers take away from the novel?
I’d like for readers to feel a sense of joy. I hope they will see that these very flawed, occasionally ridiculous people are a family bound by love, all doing their best to evolve in a changing world, all trying to be good. I have a soft spot for even my most spoiled and ill-behaved characters, and I hope you will too. I hope it makes readers laugh.
You’ve described the Stockton siblings as each representing one of Brooklyn Height’s Fruit Streets: Pineapple, Cranberry, and Orange. Darley, the oldest, is the reliable but often overshadowed orange. Cord is the exuberant middle child, the exciting and effervescent pineapple. And Georgiana is the beautiful, bright, but sometimes sour, cranberry. If you had to pick a fruit to represent yourself, which would you choose?
I’m on the fence here. My first impulse was to say that I would choose the fig to represent myself. Figs are sweet but shy, inverted flowers with hundreds of blooms (I contain multitudes!). But then I saw that viral tweet about how Calimyrna figs are actually tiny, wrinkled mausoleums for female wasps who have forced their way into the fruit to lay their eggs and then died. The enzymes dissolve the wasp’s exoskeleton, so you aren’t actually noticing the wasp when you eat the fig. But honestly, after writing an entire novel where I make fun of WASPs, I feel describing myself as the fruit-wasp-crypt-keeper is a little on the nose. So, instead of the fig, I choose the avocado. Avocados are crowd-pleasers; they have “good fat”; and they have wrinkly skin. C’est moi!