Pineapple Street by Jenny Jackson
Jenny Jackson is a vice president and executive editor at Alfred A. Knopf. A graduate of Williams College and the Columbia Publishing Course, Jenny lives in Brooklyn Heights with her family. Pineapple Street is her first novel. Let us find is this the best debut read for the month.
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Table of Contents
Description of the book:

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.
Pineapple Street Short Summary in Our Words:
In her latest novel, Jenny Jackson invites readers to immerse themselves in the world of the ultra-wealthy Stockton family, who are part of the one percent of New York’s elite society. With a focus on character development, Jackson takes a compassionate approach as she explores the lives of three women who are connected to the family.
Darley, the eldest daughter, gave up her high-paying job to raise her children, but now finds herself struggling to maintain the family’s economic security and luxurious lifestyle after her husband refuses to sign a prenuptial agreement. Sasha, who signed the prenup and married into the family, finds it difficult to navigate the family’s strict rules and customs, while Georgiana, the youngest daughter, struggles to find her place in the family and eventually faces tragedy after falling for the wrong man.
Throughout the novel, the Stocktons are forced to re-evaluate their lives and perspectives as they encounter challenges and their eyes are opened to new experiences. The author sheds light on the often-overlooked issues affecting the extremely wealthy, such as the potential for unearned wealth to skew one’s perspectives and trap individuals within their own social circles.
Despite the serious themes, the novel is a delightfully entertaining and engaging read, offering an escape into the opulent world of the Stockton family. From the children’s discovery of a dead pigeon in the park to the various celebrations and events that the family hosts, Jackson provides a vivid and immersive portrayal of the family’s lifestyle.
Overall, Jackson’s novel is a compelling exploration of family, marriage, wealth, and class, with a focus on the experiences and perspectives of women. The author’s compassionate approach and engaging writing style make this novel a must-read for fans of character-driven fiction.
Pineapple Street’s Review:
The heart and humor of Pineapple Street are both so substantial that I can’t quite determine which one is more impressive. The novel is a delightful and delectable treat, filled with clever twists and turns that left me completely engrossed.
I can’t remember the last time I read a book that was simultaneously so heartwarming and hilarious. A word of caution: once you start reading, you won’t want to put it down until you’ve reached the end.
This book is an absolute treasure, and I highly recommend it to anyone who enjoys a good read.
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