book cover of Pineapple Street
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Pineapple Street

A novel by

A Good Morning America Book Club Pick

“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

“A delicious new Gilded Age family drama… a guilty pleasure that also feels like a sociological text.” —

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.

Genre: Literary Fiction

Praise for this book

"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

"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

"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

"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

"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

"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

"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

"Jenny Jackson delivers SUCH a delicious treat with her debut novel, Pineapple Street. It delights across the board - character (the wealthy, quirky Stockton family), setting (an insider's look at Brooklyn) and plot (a searingly honest exploration of class and privilege.) With shifting points of view and smart, laugh-out-loud observations on every single page, Pineapple Street is an instant classic." - Elin Hilderbrand

"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

"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

"Full of witty and caustic observations about a privileged class of New Yorkers, Pineapple Street is a sharp and juicy satire." - Nita Prose

"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

"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

"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

"Pineapple Street might be the Edith Wharton novel for our times... Wise, funny, tender, and utterly relatable." - Susie Yang

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