If you are having difficulty navigating this website please contact us at member.services@bookofthemonth.com or 1-877-236-8540.

Get your first book for $5 with code PASTEL at checkout.

Join today!

We’ll make this quick.

First, enter your email. Then choose your move.

By tapping "Pick a book now" or "Pick a book later", you agree to Book of the Month’s Terms of use and Privacy policy.

Pineapple Street by Jenny Jackson
Literary fiction

Pineapple Street


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

by Jenny Jackson

Excellent choice

Just enter your email to add this book to your box.

By tapping "Add to box", you agree to Book of the Month’s Terms of use and Privacy policy.

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, Icon_FamilyDrama

    Family drama

  • Illustrated icon, Icons_Millenial


  • Illustrated icon, Icons_Buzzy


  • Illustrated icon, Icon_Nyc



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.

Read less

Free sample

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


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.

Create a free account!

Sign up to see book details, our quick takes, and more.

By tapping "Sign up", you agree to Book of the Month’s Terms of use and Privacy policy.

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.

Read less

Member ratings (6,289)

  • Carrie B.

    Colonial Heights, VA

    I wasn’t sure if I’d like this one,it’s not my usual genre,however I loved it!Witty, insightful & well written.I couldn’t wait to see how each of the well written characters & story lines developed!

  • Kennedy O.

    Indianapolis, IN

    Loves how this wasn’t some huge scandal or mystery. It’s a story of an rich family with its own interpersonal issues. It’s like Succession, but the characters actually have some redeeming qualities

  • Allison A.

    Prosper, TX

    This book is a gem. I truly enjoyed each characters story and growth throughout the entire novel. A very strong debut book. I’m excited to see what the author produces next! Treat yourself. Read this!

  • Nicole Y.

    Olympia, WA

    A book that proves that is written that the wealthy aren’t immune to family drama. Everyone has their own perceptions and judgements that contribute to the dysfunction and some remain in their denial.

  • Mathea C.

    Vancouver, WA

    3.5⭐ In between "liked" and "loved" for me but definitely worth a read. Nothing really happens but it's still interesting to peer into the lives of the rich - maybe it's not all it's cracked up to be.

Create a free account!

Sign up to see book details, our quick takes, and more.

By tapping "Sign up", you agree to Book of the Month’s Terms of use and Privacy policy.