Pineapple Street: A GMA Book Club Pick
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A New York Times bestseller A Good Morning America Book Club Pick
Chosen as a best book of the year by The New York Times Time NPR USA Today Elle Harper's Bazaar Town & Country Vogue BBC POPSUGAR Goodreads theSkimm
"The season's first beach read, a delicious romp of a debut featuring family crises galore."-- The New York Times
"A delicious new Gilded Age family drama... a guilty pleasure that also feels like a sociological text." --Vogue
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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Book Details
- ISBN
- 9780593490716
- Binding
- Paperback
- Authors
- Jenny Jackson
- Publisher
- Penguin Books
- Published Date
- March 12, 2024
- Language
- English
- Pages
- 336
- Physical Info
- 0.8 in H x 7.8 in L x 5.2 in W (0.5 lb)

A fun if uncomfortable read - dipping your toe into the lives of the 1% and barely tolerable characters. But it hummed along and was enjoyable. Just.
I loved this book!
This book was an interesting look into the world of the wealthy. The character development was very good and it brought up many life experiences we all have in common whether we are rich, poor or middle class. Thanks for the good read!
Enjoyable, light reading book but it seemed to end so abruptly. Everything wrapped up in just a couple of pages. Left me unsure of the purpose of the story.
This book was over the top, for everyone’s “awakening”. It was too much. The writing was good, easy to read
- 5 stars: 6 (30%)
- 4 stars: 9 (45%)
- 3 stars: 5 (25%)
- 2 stars: 0 (0%)
- 1 star: 0 (0%)
A fun if uncomfortable read - dipping your toe into the lives of the 1% and barely tolerable characters. But it hummed along and was enjoyable. Just.
I loved this book!
This book was an interesting look into the world of the wealthy. The character development was very good and it brought up many life experiences we all have in common whether we are rich, poor or middle class. Thanks for the good read!
Enjoyable, light reading book but it seemed to end so abruptly. Everything wrapped up in just a couple of pages. Left me unsure of the purpose of the story.
This book was over the top, for everyone’s “awakening”. It was too much. The writing was good, easy to read
I thought this book was a fun read but there's no depth to it. It's about the typical wealthy, socially disconnected white family with some very forced self realization added. It falls flat after the first 3/4 like the author was trying to wrap it up before she lost all creativity. I think if you need something mindless to read that makes you smile this is the perfect book; especially if you can relate to the gentrification that is Brooklyn.
Fun and funny characters. Smooth transitions. Contrived conclusion. Try Jane Austen for family chaos.
Enjoyed hearing the woes of having money and seeing it’s not all that it seems. Family dynamics at its best and worst. Slow start but the character building is worth it
This was a good book, quick read, but still fascinating. The overall wealth, while a bit cumbersome to read about, made the book enjoyable!
Finished the book in one day, it was a nice book that had a good flow. About rich folks and each character was well written.
I was so caught up in reading historical novels and watching the news that this was a good break from that.I did feel like the characters could be developed more, maybe a part 2 where we hear from the guys. Also I feel like there were some loose ends.
This story tells us about a wealthy family in NewYork. The couple have three kids. Cord, Dalia, and the youngest who is 26 Georgiana. Chip and Tilda, are in charge of there trusts. Most of which is tied up in real estate. Cord works with his father and is newly married. His wife Sasha is middle class and not included in their inner circles. Dalia is married to Malcolm and have two children. Malcolm had a good paying job until he was fired. Malcolm also was considered below the Stocktons but was excepted because he signed the prenupt. Georgians and Davis were spoiled entitled young women. Georgians is single who fell in love with a married man and didn't know he was married until she fell hard for him. Sasha and Cord lived in the family home which the two daughters resented and took it out on Sasha. They learned along the way that money doesn't buy happiness. They went through some life's lessons! It was very interesting and I highly recommend this book!
What a refreshing read! The writing is fabulous and the story is unique and interesting with no hint of a formula in the plot .Sometimes good writing inhibits readability with verbose descriptions and evasive subtlety. Not the case here! The writing compliments this easy-to-read story that covers a host of topics: including marriage, social classes in America, money and family secrets.On the whole, I found it thought-provoking and nuanced. Even the title, which seemingly refers to an established Brooklyn Heights fruit street, has a layered meaning that ties back to the plot.I recommend to anyone looking for an easy read with some depth.
I really enjoyed this novel. I admit that it was tough at the beginning to warm up to these fabulously rich characters. Told from the viewpoints of Sasha, Darley, and Georgiana. The Stockton family is beyond wealthy, they makeup the 1% everyone always hears about. They are odd in many ways but their love of family is deep. Darley, is the eldest daughter. She is married to the love of her life. Darley is a great character. She loves her family with all her heart. She especially loves her husband Malcolm. Sasha has married into the Stockton family. She was raised in a middle class household. Sasha finds it difficult to fit into the Stockton family. She is more of an outsider and she begins to chafe under the burden of always coming second in this family. My least favorite character is Georgiana, the baby of the Stockton family. She is a spoiled brat with little regard how other people feel. Though Georgiana does manage to grow in the novel, I still didn't like her.
Pineapple Street is a fascinating look at the upper-crust Stockton family. Their money is old money. They are self-pronounced typical WASPs and are not quite ready for their millennial children to question their values and long-proven lifestyle choices.Tilda and Chip Stockton are the parents of Darley, Cord, and Georgiana. Cord and his wife Sasha live in the family home in Brooklyn Heights in the prestigious fruit streets on Pineapple Street. Since Sasha is of middle-class roots and has far less status than the Stocktons, she is supposed to feel honored to keep everything decorated in the old classic way and maintain the childhood rooms of Cord's siblings precisely as they left them.Darley is married to Malcolm, an Asian. Darley is confident in her husband's ability to provide for her and has therefore chosen to forego a career and her family inheritance since she didn't want to require Malcolm to sign a prenuptial agreement, which is commonplace and routine when someone marries into the Stockton family. She seems surprised that her children are targets of subtle Asian discrimination, even from her family.Georgiana is the youngest and much younger than her siblings. She works at a nonprofit and realizes her values do not mesh with her family's. She is also uniquely sensitive to the subtle and overt biases inherent in many wealthy one-percenters. Georgiana grows influenced by some other millennials unwilling to perpetuate some cultural systems that have allowed families such as hers to enjoy their wealth.The author masterfully creates an easy-to-read story that delves into American social classes, the politics of MONEY, and family secrets. Contemporary societal issues are addressed through the novel's events and dialog. It is thought-provoking, and its contents are many-layered. Even the title, although seemingly innocuously referring to an established fruit street in Brooklyn Heights, should give us pause. The book's text is, "Did you know that the pineapple symbolizes welcome and hospitality?" This follows: "We think of pineapples as this whimsical fruit, but they're actually a symbol of colonialism and imperialism."
Brimming full of dark humor, “Pineapple Street” is a social satire of New York’s 1 Percent (think HBO dark comedies like ‘The White Lotus’ and ‘Succession’ bred with the Old vs. New Money characters in ‘The Gilded Age’). “Pineapple Street” is about three women trying to make their way in the wealthy Stockton family: Sasha, the sister-in-law (perceived to be a Gold Digger by her new family, but just plain misunderstood); Darley, a burnt-out, stay-at-home mom of two little morbid kids trying to keep her family at the top after her husband is fired from his executive job; and the baby sister, fittingly named Georgiana, at the center of the family’s orbit. As Sasha attempts to acclimate to her new marriage and her new four-story townhouse (her husband’s family’s home bequeathed to her husband by his classist yet endearing parents) on Brooklyn’s posh Pineapple Street, Darley and Georgiana work to thwart Sasha’s attempt at establishing herself as a Stockton. The plot is basic, but it’s character-driven, and the novel’s themes of social problems, elitism and nepotism are very timely. Although “Pineapple Street” has become one of my new favorites, I felt it was a little short in length and missed the mark by wrapping up the conflict too quickly (I suspect there will be a sequel).
"Pineapple Street," by Jenny Jackson followed the lives of the uber wealthy Stockton Family, most of whose fortune was inherited and that they continued to grow as real estate moguls. Chip and Tilda were the parents in their 70s, and their adult children were Cord, Georgiana, and Darley. All the accoutrements of wealth were present in every chapter. For the children, whose points of view varied widely and changed throughout the book, their privilege might have been either a blessing or a curse which commanded certain standards of conduct and carried obligations. Caught up in lavish social events and the most expensive of homes, apartments, private schools, and colleges, the Stockton children were forced to navigate sensitive prenups and have financial experts manage their trust funds. Sasha, who married Cord, and Malcolm, who married Darley, were outsiders living in the Stocktons' world, accepted only superficially. The book was interesting in that it revealed the self indulgences of the upper crust families who occupied Brooklyn Heights within a world of servants and nannies. No clothes were too expensive to attend an endless stream of extravagantly themed parties. Secrets ruled the day as Malcolm hid his unemployment and Georgianna hid her extramarital affair. The book evoked a range of emotions for me, as I felt disdain for the super-rich who squandered their funds on personal gratification, and I felt sorry for the those who married into the family, having to sacrifice a lot of their own family connections. It was more rewarding to read about the redemption of certain characters as they experienced personal growth and sought to establish their own identities. By the book's end, the emergence of two philanthropists was unexpected and satisfying.
Meet the Stocktons of Brooklyn. They’re an old money real estate dynasty and when life throws a few curveballs their way, we’ll see how they manage.It might be a sunny day, but the air isn’t always sweet on Pineapple Street. Tilda is the obstinate matriarch whose jam is setting the perfect table, that is, when she’s not hitting a ferocious tennis ball across the court. Darling husband Chip keeps the Benjamins flowing. They have three grown children, including Darley, who renounced her trust fund and career to stay home with the kids and was against having her kind husband Malcolm sign a prenup. Georgiana is spoiled but fancies herself charitable because she works for a non-profit, she’s also in love with an unattainable man. Sasha, an artist, married into the family (husband Cord manages the family’s money with dad) and the sisters treat her like an outcast, having given her the oh so subtle moniker “gold digger.”Drama and humor abound, making this fast-paced zeitgeisty plot highly entertaining. But don’t expect to hate these one-percenters, you’ll be too busy being entertained. Gawking into the window of a house that’s suspended in time, the not always smooth dynamic between siblings, games that are more competitive than fun, holidays that are for show rather than sentiment, it’s the insiders versus the outsiders.Read it if you like to escape into other dysfunctional families and you love your books sprinkled with wit and secrets. Stay to see how three women divide and conquer class and inherited wealth.
I really liked this readable book. The characters were perfectly written and the story almost relatable. I say "almost" because the idea of a family with old millions whose children felt the need to divest themselves of their millions is a cliched millenial anthem. It sounds noble but is hard to believe. This family lives in NYC with multiple residences and the progeny suffer from rich guilt. One hopes there will be a follow up novel about how sacrificing their wealth honestly enhances their lives.I felt the book was written to mirror the " shame the rich" ethos so popular now.It was well written and the characterizations were excellent. It lost a star because I am tired of this theme.
This book opens with a bang--strong satire, and you think you're going to have an arch, withering look at the uber-rich in Brooklyn, an updated Preppy Handbook or even Bonfire of the Vanities. But quickly, the humor fades, and you find one of the whitest group of people with more money than God getting and keeping just about everything they have ever wanted (unless they give it away). No Blacks, not ONE gay (except Truman Capote's ghost)--and this is Brooklyn!--and only a smattering of Koreans. If the novel had continued satirizing this freakishly vanilla world I could have enjoyed that ride, but the level of tension is so low--the novel is more like a background character notebook for the inevitable mini-series that will come from this. And the author is one of the most powerful editors in the business? She wrote a 300-page book, but I wouldn't call it a novel--it doesn't have the kind of strong conflict that any decent YA book has these days. The book promised something hip and sharp like The Nanny Diaries or The Devil Wears Prada, but it falls flat. Still, it has spin, it has a high concept, and it's so white--I expect it will sell like hotcakes, especially in the Hamptons.
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