Pineapple Street

Description

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

“A vibrant and hilarious debut…Pineapple Street is riveting, timely, hugely entertaining and brimming with truth.” —Cynthia D’Aprix Sweeney, New York Times bestselling author of The Nest

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.Praise for Pineapple Street:

“Pineapple Street is that rarest of gifts—a novel you don’t want to put down for anything. Transporting and laugh-out-loud funny, this intergenerational story is a perfect tale for our times.”
—J. Courtney Sullivan, New York Times bestselling author of Friends and Strangers

“In this vibrant and hilarious debut, Jenny Jackson has taken a familiar tale—siblings, family money, competing interests—and given it fresh life. What binds the book together so wonderfully is Jackson’s keen understanding of the beauty and difficulty of belonging, of how our desires can clash with our inherited narrative and what happens to the people we love when we need to rewrite the story. Pineapple Street is riveting, timely, hugely entertaining and brimming with truth.” 
—Cynthia D’Aprix Sweeney, New York Times bestselling author of The Nest and Good Company

“Set in the windy, sun-dappled streets of Brooklyn Heights, Pineapple Street is a portrait of a NY family strait-jacketed by their own wealth that is at once searing, hilarious and poignant.”
—Miranda Cowley Heller, #1 New York Times bestselling author of The Paper Palace

“I loved Pineapple Street. The characters are complex and engaging and their stories bring a particular slice of New York magically alive. So wise, emotionally honest, and such fun!”
—Helen Fielding, #1 bestselling author of Bridget Jones’s Diary
 
“Full of witty and caustic observations about a privileged class of New Yorkers, Pineapple Street is a sharp and juicy satire.”
—Nita Prose, #1 New York Times bestselling author of The Maid 

“I was entranced by Pineapple Street. Smart and complex, rich and gorgeous, this novel drew me in from page one. Both an escape into the lives of the fabulously wealthy and a bittersweet examination of family and heartbreak, Jenny Jackson’s debut left me eagerly awaiting whatever magic she conjures next.”
—Amanda Eyre Ward, New York Times bestselling author of The Lifeguards

“I’m not sure which is bigger: Pineapple Street’s heart or its humor. It’s smart and surprising and, yes, scrumptious. I devoured it. I can’t recall the last time I read a novel that was both this heartwarming and this hilarious. One word of advice: clear your calendar before you start reading. You won’t stop until you’ve finished. It is, pure and simple, a treasure.”
—Chris Bohjalian, #1 New York Times bestselling author of The Flight Attendant and The Lioness
 
“Nothing beats a story told this well…. I could not stop laughing at this hilarious insider’s view of Brooklyn Heights WASPs. Truly the smartest and most deliciously fun novel I’ve read in ages.”
—Kevin Kwan, New York Times bestselling author of Crazy Rich Asians

“Pineapple Street might be the Edith Wharton novel for our times…Wise, funny, tender, and utterly relatable.”
—Susie Yang, New York Times bestselling author of White Ivy

“A delight to read from start to finish, Jenny Jackson’s Pineapple Street is a cancel-all-plans kind of book. Utterly addicting, big-hearted and affecting, and full of delicious details, Jackson lets us into an outrageous world of generational wealth and privilege through the eyes of three fallible yet lovable women navigating the complexities of life on the inside. If I could have put this novel on a drip straight into my veins, I would have!”
—Ashley Audrain, New York Times bestselling author of The Push

“If you’re in search of the fiction trifecta – a captivating story that’s masterfully constructed, vividly peopled, and crisply written – look no further. Jenny Jackson’s “Pineapple Street,” is pure reading pleasure, hilarious, big-hearted, and full of emotional truths. It’s the kind of novel you hope will never end.”
—Adrienne Brodeur, New York Times bestselling author of Wild Game

“Jenny Jackson has written a lovely, absorbing, acutely observed novel about class, money and love. These are the themes of Henry James and Jane Austen, but they are observed with a fresh eye and a contemporary voice. Who wouldn’t want to read Pineapple Street?”
—Nick Hornby, New York Times bestselling author of Just Like You

“I devoured Pineapple Street. Jackson’s writing brims with wit and warmth. Her characters are deliciously flawed and, at the same time, loveable and compelling. Her observations about family, money, class, and love are spot on….[A] messy, hilarious and ultimately relatable family story.”
—Cristina Alger, New York Times bestselling author of Girls Like Us

“I sucked it down like a milkshake… My favorite part of the novel was the heart. All the characters mess up, but make amends. They TRY. And they keep trying.”
—Helen Ellis, author of Bring Your Baggage and Don’t Pack LightJenny 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.
 

1. 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?

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?

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