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Pineapple Street by Jenny Jackson

Literary fiction

Pineapple Street

Debut

We love supporting debut authors. Congrats, Jenny Jackson, on your first book!

by Jenny Jackson

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Volume 0
Volume 0

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Quick take

Brooklyn’s 1% is put under the microscope in this sharp, vibrant exploration of what happens to a trust fund deferred.

Good to know

  • Illustrated icon, Family_Drama

    Family drama

  • Illustrated icon, Millenial

    Millennial

  • Illustrated icon, Buzzy

    Buzzy

  • Illustrated icon, NYC

    NYC

Synopsis

Darley, the eldest daughter in the well-connected, carefully guarded, old-money Stockton family, followed her heart, trading her job and inheritance for motherhood, sacrificing more of herself than she ever intended. Sasha, middle-class and from New England, has married into the Brooklyn Heights family and finds herself cast as the arriviste outsider, wondering how she might ever understand their WASP-y ways. Georgiana, the baby of the family, has fallen in love with someone she can’t (and really shouldn’t) have and must confront the 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. It’s about the peculiar unknowability of someone else’s family, the miles between the haves and have-nots and everything in between, and the insanity of first love.

Free sample

Get an early look from the first pages of Pineapple Street.

Pineapple Street

Prelude

Curtis McCoy was early for his ten o’clock meeting so he carried his coffee to a table by the window, where he could feel the watery April sun. It was a Saturday, Joe Coffee was crowded, and Brooklyn Heights was alive, women in running tights pushing strollers along Hicks Street, dog walkers congregating at the benches on Pineapple Street, families dashing to soccer games, swimming lessons, birthday parties down at Jane’s Carousel.

At the next table, a mother sat with her two adult daughters, drinking from blue-and-white paper cups, peering at the same phone.

“Oh, here’s one! This guy’s profile says he likes running, making his own kimchi, and ‘dismantling capitalism.’”

Curtis tried not to listen but couldn’t help himself.

“Darley, he’s twice my age. No. Do you even understand how the app works?”

The name Darley rang a bell, but Curtis couldn’t quite place her. Brooklyn Heights was a small neighborhood, she was probably just someone he’d seen in line ordering sandwiches at Lassen, or someone he’d crossed paths with at the gym on Clark Street.

“Fine, fine. Okay, this guy says, ‘Cis male vegan seeks fellow steward of the Earth. Never eat anything with a face. Except the rich.’”

“You can’t date a vegan. The footwear is ghastly!” the mother interrupted. “Give me that phone! Hmm. The whiffy here is terrible.”

“Mom, it’s pronounced ‘wai-fai.’”

Curtis risked a quick peek at the table. The three women were dressed in tennis whites, the mother a blonde with gold earrings and a notable array of rings on her fingers, the daughters both brunette, one lanky with straight hair cut to her shoulders, the other softer, with long wavy hair loosely tied in a knot. Curtis ducked his head back down and broke off a crumbly bite of poppyseed scone.

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Why I love it

We’ve all encountered one of those families before—two patrician parents and their three beautiful adult children, meeting up for brunch or tennis or slipping into an old brownstone for cocktails around a fireplace, all of them fascinating and elusive because you sense they prefer each other’s company to everyone else’s and in no way will you ever truly be able to penetrate their small and enticing world. Well, I have good news: Jenny Jackson’s Pineapple Street takes you into the inner world of one such family and it’s a delicious, funny, and surprisingly moving ride.

Set in Brooklyn Heights, this story is about the three wealthy Stockton siblings, and Sasha, the small-town outsider who marries into the family. There’s plenty of secrets, repressed resentments, and snarky judgements. I particularly loved Sasha’s (very relatable) struggle with getting rid of the clutter inside the brownstone her in-laws allow her to live in rent-free without incurring her mother-in-law’s wrath.

What I appreciated most about the novel is that these characters may seem at first like types, but as we follow their individual struggles we see all the complexity lurking beneath the surface of our caricatures. In fact, I rooted for these characters. I felt for them the way I would for a friend. Turns out money can’t protect them from marital problems or career setbacks or loss. When you finally enter the inner circle, you realize that the perfect-seeming family is just like any other family. That, in the end, is this book’s greatest reward.

Member ratings (6,835)

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View all
Intermezzo
The Book of George
Real Americans
Dirty Diana
Wellness
Margo’s Got Money Troubles
The God of the Woods
Same As It Ever Was
Annie Bot
Bear
Mercury
True Biz
Family Happiness
The Lady Waiting
The Other Valley
Hard by a Great Forest
Good Material
The Bullet Swallower
Happy All the Time
Rental House
Alice Sadie Celine
Let Us Descend
Tomorrow, and Tomorrow, and Tomorrow
Shark Heart
Homeseeking
Transcendent Kingdom
Hello Beautiful
Dominicana
What's Mine and Yours
The Unsettled
Ask Again, Yes
Vladimir
Infinite Country
The Prophets
Normal People
The Verifiers
Salvage the Bones
The Many Daughters of Afong Moy
I Have Some Questions for You
Black Buck
The History of Love
Age of Vice
Paper Names
The Light Pirate
The Secret History
The Kite Runner
Memorial
The Half Moon
Happiness Falls
The Gifted School
The Death of Vivek Oji
The Knockout Queen
Little Monsters
Yerba Buena
Beautiful World, Where Are You
Free Food for Millionaires
A Burning
The Mothers
The Water Dancer
Small Country
The Sympathizer
Fleishman Is in Trouble
Lot
An American Marriage
The Animators
The Mars Room
Exit West
White Fur
Woman No. 17
The Ministry of Utmost Happiness
Eat Only When You're Hungry
Rainbirds
A Ladder to the Sky
Golden Child
The Goldfinch
The Love Affairs of Nathaniel P
& Sons
The Association of Small Bombs
Lolly Willowes
All Grown Up
Marlena
Signal Fires
Someday, Maybe
Woman of Light
Marrying the Ketchups
The Shards
Blue Sisters