Pineapple Street: A GMA Book Club Pick (A Novel)

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.

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Published Mar 7, 2023

Average rating: 6.11

663 RATINGS

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Community Reviews

thenextgoodbook
Sep 04, 2025
8/10 stars
thenextgoodbook.com

What’s it about?

The Stockton family has happily lived in Brooklyn Heights on Pineapple Street for as long as they can remember. Chip and Tilda belong to a world of generational wealth and privilege- and their three adult children have known no other life. As Darley, Cord, and Georgianna age they must come to terms with their own attitudes about wealth- and the place it holds in their lives.

What did it make me think about?

What a world…. This book centers around a level of wealth that most of us will never know. It also highlights the Northeast and NYC which is quite a small world it seems. Fascinating!

Should I read it?

This was a fun novel about an interesting new phenomenon. What happens when the next generation does not see inherited wealth as a gift to maintain. What if instead they want to give away the fortune that generations have passed down? This story could have been preachy (or just made most readers gag) but the author deftly handles the material, and with kid gloves actually makes us see the humanity in the Stocktons. I myself was not a huge fan at first, but it was such an easy read I kept going. I am glad I did. My related books are all books that made me think about a topic in a different way- much like Pineapple Street.

Quote-

“Darley had noticed something about people with money: they stuck together. Not because they were intrinsically shallow or materialistic or snobbish, though of course those things could very well be true, but it was because when they were together, they didn’t have to worry about the differences their money meant in their lives. “
K Olson
Jan 10, 2025
7/10 stars
This is a character driven novel about the wealthy 1% in Brooklyn Heights. The author chose this setting because she lives there and there is a good sense of place woven into the book. There definitely is humor in the writing and it’s an interesting take to write solely from the perspective of women. The ending seemed to be a bit unrealistic in the “change” that occurs within Georgiana and the author uses the ending to espouse her political take on wealth and capitalism in our country so the characters sounded more like talking heads. I thought the concept of the millennials having a moral dilemma about inheriting wealth was really interesting- it just needed to be executed better.
neverenoughali
Nov 13, 2025
DNF
Margie Pettersen
Oct 27, 2025
8/10 stars
I wasn't sure about this book when I started it, but quickly became drawn into the complicated lives of the Stockton children: Darcy, Cord, and Georgiana, all trust fund children who had lived sheltered lives. Darcy is married to Malcolm and decided to divest herself of her trust fund rather than have her husband sign a pre-nup. Cord is married to Sasha, who is called GD (gold digger) by his sisters. His parents are letting them live in the family home, but Sasha never feels quite at home. The youngest sister, Georgiana is still single and has her own dilemmas. Overall, I enjoyed reading this book and couldn't wait to find out what the next drama was for the Stocktons.
Pansy
Oct 09, 2025
6/10 stars
Better than a 3 but not a four

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