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Pineapple Street

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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.

Shot through with the indulgent pleasures of life among New York’s one-percenters, Pineapple Street is an addictive, escapist novel that sparkles with wit. Full of recognizable, lovable—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 deliciously funny, sharply observed debut of family, love, and class.

304 pages, Hardcover

First published March 7, 2023

About the author

Jenny Jackson

1 book1,533 followers

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5 stars
26,939 (14%)
4 stars
72,743 (39%)
3 stars
65,399 (35%)
2 stars
15,921 (8%)
1 star
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Displaying 1 - 30 of 17,253 reviews
Profile Image for Dennis.
916 reviews1,879 followers
March 14, 2023
The cover and the idea that this is a modern-day Guilded Age type of story really drove me to purchase and read Jenny Jackson's debut novel, PINEAPPLE STREET. I was hoping for a rich family behaving badly type of troupe, but ultimately nothing really happens in the book. Like nothing. I legit finished the story and was like, what was the purpose? We get a voyeuristic view into a world of family dynasty wealth and cattiness, but otherwise nothing happens. I mean, obviously things happen because it's 300 pages, but nothing that really made me interested in bringing up in my review. The cover is nice though.
Profile Image for Anne Dragovcic.
257 reviews74 followers
November 27, 2023
Yet ANOTHER novel written by an editor of a major publishing company. *Sigh*

I DNF’d it due to lack of a plot line, use of arcane descriptors, unlikable characters along with my own lack of desire to explore the exploits of the fictional 1%.
(Can a well educated woman really NOT know the UAE 🇦🇪 is a country ?!)

I didn’t have it in me to get to the skewering which is what I’m sure will be the “enjoyable” part of the book.

The target audience is probably Gen Z as they come of age. Jackson is trying way too hard to be a modern Jane Austen and she fails at every level. Jackson is in dire need of a good editor. Ironic.
Profile Image for Val ⚓️ Shameless Handmaiden ⚓️.
1,976 reviews34.1k followers
May 8, 2023
3 Stars

I feel somewhat conflicted about this book...

On one hand, this was a very slow-moving, character driven story about a dysfunctional wealthy family...and I am always down for all of those things. I always LOVE a good familial shit show.

I also read this in one sitting, which for me always garners a star.

I did feel like the family evolved in some small way (sort of) over the course of the story; however, I can't decide whether or not the author meant this as some sort of discourse on wealth and privilege...or not. I wasn't quite sure. And then I read in the author notes that Jenny Jackson is a publishing executive who lives in the very neighborhood this book is centered on...Hmmmm...so, tongue-in-cheek poking or self-flagellation/virtue-signaling?

I have no idea.

Regardless, I loathed Georgiana. LOATHED. And I'm sorry, she can give all her money away every day (but still have her $37 million and future inheritance from her parents, mind you), spout all the woke bullshit under the sun, and virtue-signal like a boss...she is still a bad person. And it's not the money's fault.

My favorite character in the book was Tilda. At least she owned who she was with no apology.
Profile Image for Jess.
244 reviews
March 12, 2023
Short version: are we sure this isn't YA?! It's a boring book about super immature entitled people that will delight anyone who loved Spare and has great compassion for the prince who can't stop whining. Ultimately, Pineapple Street is a novel that deeply defends wealthy people even amidst the few surface admonishments.

Long version:
Here we have a privileged white woman writing a book about overly privileged white people in which the only BIPOC characters provide financial support or childcare. Yet another publishing exec takes up space that should have gone to a talented writer with something to say.

The first 50% of the book is just descriptions of rich people's lives. The 1%. That's it. Zero major plot points besides a few occurrences that happen to us lowly 99% with regularity. Nothing happens except for petty insults and power plays.

The second half of the book isn't much better. No real plot beyond some theoretical life changes. And oh, the repitition! Girl, get a job if you feel that guilty about "not using your education." This self-indulgent refrain occurred again and again and again.

I was also annoyed by the numerous talking points about contemporary social issues culled from headlines with no nuance or understanding of the actual suffering behind those words.

I must repeat: this is a novel that deeply defends wealthy people even amidst the few surface admonishments. It's the worst kind of virtue signalling from a VP in an industry that has a real problem with white supremacy.
Profile Image for Paromjit.
3,080 reviews25.7k followers
November 24, 2022
Jenny Jackson writes a delightfully entertaining character driven novel that immerses the reader into the Stockton family members, their rarefied social circles, and well connected lives of unimaginable wealth and privilege that comprises the New York world of one percenters. Taking a human and compassionate approach, the author gently examines and sheds light on some of the issues affecting the extremely rich through the lives and thoughts of 3 women. Darley is the eldest daughter who preferred to lose her family money rather than have her beloved husband, Malcolm, sign the expected prenup. She gave up working at Goldman Sachs to bring up her 2 young children, Poppy and Hatcher with the family relying on Malcolm's salary, their circumstances becoming more difficult when their economic security and lifestyle come under threat.

Sasha signed the prenup and married into the family, her husband Cord's life revolves around his family, his priority, he works with his father, Chip, in their real estate investment firm, and rubs his mother, Tilda's feet. They live in the family home at Pineapple Street at Brooklyn Heights, where any effort by Sasha to clear the house of its clutter or make any changes is stymied. Sasha finds it impossible to enter the inner family sanctum, she is shut out, and she can barely understand the Stocktons strange rules, culture and rituals. Georgiana is the youngest daughter, she plays tennis with Tilda, her only means of connection, otherwise there would be no communication with a Tilda whose life revolves around tennis, tablescapes, celebrations, such as the gender reveal party, and avoiding any form of conflict, making honest conversations out of the question. Georgiana's life begins to unravel after she falls for a man that is really no good for her, and which ends in a tragedy she is ill equipped to deal with.

The Stocktons find themselves re-evaluating their lives after their eyes are opened in a number of critical areas, with the lonely Georgiana wondering whether she is a good person after all, and questioning, like Curtis McCoy, whether such vast inheritances, all unearned wealth, might skew their perspectives, trapping them within the tiny group of those who are just like them, and the often erroneous assumptions they make about themselves and everyone who does not belong. Darley finds herself finally beginning to comprehend the difference between sharing and being taken advantage of and the pregnant Sasha sees herself more clearly on returning to her Rhode Island family home, her faith in her marriage restored with Cord turning up to support her. This is a wonderfully escapist, easy, engaging and fun read, of family, I loved how Darley's children pick up a dead pigeon in the park, of marriage, wealth, class, and the position of women. Many thanks to the publisher for an ARC.
Profile Image for Chris.
Author 36 books12.4k followers
August 23, 2022
I’m not sure which is bigger: Pineapple Street’s heart or its humor. It’s smart and surprising and, yes, scrumptious. I devoured it. I can’t recall the last time I read a novel that was both this heartwarming and this hilarious. One word of advice: clear your calendar before you start reading. You won’t stop until you’ve finished. It is, pure and simple, a treasure.
Profile Image for Tatiana.
1,473 reviews11.4k followers
March 25, 2023
What in the world was this and how much money was spent to put this book on “best of” lists? Granted, I am automatically predisposed not to like books about ultra rich, but this one didn’t even have a point. Rich people have all advantages in the world, and one of them sort of tries to break the mold by becoming a white savior. Why did I read this?
Profile Image for emilybookedup.
481 reviews7,100 followers
March 16, 2023
update, i finished it—safe to say that so far in 2023, lit fic family dramas are not my cup of tea 😅🍵 (enter: HELLO BEAUTIFUL)

to be honest, the only things i can say about this book are:
- the cover is my favorite part and is deff what made me buy it
- there was NO plot. i felt like i was just solely reading inner characters monologues and kept thinking “okay, but what is the point?” or “is something ever going to happen?”
- there were maybe 2 interesting things that happened “plot” wise in all 300 pages
- i didn’t like any of the characters
- i didn’t really understand the point
- the way the rich & elite behaved in this book made my stomach hurt
- i have no idea how this will be a tv series unless it’s 100% reimagined, because 80% of the book is inner monologue

all that aside, clearly this is is a buzzy book and readers are picking it up and talking about it—it made the NYT bestseller list as well as a GMA Bookclub pick!

if you like family drama, rich & privileged characters and don’t need a ton of action in books to enjoy them, maybe it’s worth checking out for yourself
Profile Image for Alexandra (Lexi) Roselyn.
60 reviews10.8k followers
May 13, 2023
5 stars. Hilarious, entertaining, and a lot of great commentary. I think more people should pick this up- it’s a GREAT book!!!!
Profile Image for Brandice.
1,090 reviews
March 31, 2023
Pineapple Street isn’t about rich people behaving badly, in the traditional sense, but it is a rich people with first world problems book. The Stockton family is incredibly wealthy and all reside in close proximity to one another on streets named after fruits in posh Brooklyn Heights.

The story is told from sisters, Darley and Georgiana, and their sister-in-law, Sasha. Darley chose to give up her inheritance in order for her husband to avoid signing a prenup. He is a successful banker and they’re doing just fine, for now. Sasha married Cord, the middle child of the Stockton family, and tries to accept the family’s extreme level of closeness. Sasha didn’t come from a family with this type of wealth and doesn’t always feel welcomed by them. Georgiana is the baby and after falling for the wrong guy, she begins to spiral and question the life she was raised having.

There is some action in Pineapple Street but it’s not fast paced. There is a lot of inner contemplation by the characters. I love this book cover and while the details of the story may not stick with me long term, I enjoyed reading it.
Profile Image for Samuel Gordon.
78 reviews1 follower
March 12, 2023
Perfectly readable but felt completely pointless by the last few chapters as if unsure about what it wants to say about Old Money and trust fund babies. Despite clocking in at just under 300 pages, the resolution felt too slapdash and anti-climactic that I think the author missed an opportunity to dig deeper and challenge its characters to do more than just surface-level soul-searching.
Profile Image for Aoife Cassidy McM.
712 reviews275 followers
May 2, 2023
Written by a publishing exec, Pineapple Street is one of those books that has been marketed heavily for months now. But is it actually any good?

It’s the story of the Stocktons, an über wealthy family living in Brooklyn Heights whose generational wealth was acquired through property. They’re pampered, privileged, well-educated but still don’t know that the UAE is a country.

We meet Tilda and Chip, their children Cord (short for Cordington), Darley and Georgiana. Cord has married beneath him to Rhode Island graphic designer Sasha. Darley married her true love Malcolm, a wealthy investment banker of Korean heritage. Georgiana is working for a non-profit and going through a quarter-life crisis.

I was expecting something witty, biting, clever, ironic - rich people swiping and sniping - but Pineapple Street was none of these things. I found the book pretty bland.

The writing is good/perfunctory, but there’s an absence of plot, a lack of depth to the characters, and a heavy-handed approach to social issues like racism, classism, gentrification - I actually winced reading some of the statistics blatantly dropped in at times without a hint of irony. It’s about as subtle as the Stocktons are self-aware.

Sure, it’s an easy read but it’s dull, riddled with stereotypes and that abrupt ending and weird epilogue read like a pointless afterthought. There are many better books out there this year that haven’t received a fraction of the hype this one is getting. 2/5⭐️

*Many thanks to the publisher for the arc via @netgalley. Pineapple Street was published on 13 April. As always, this is an honest review.
Profile Image for Liz.
2,503 reviews3,387 followers
April 1, 2023
I will admit I thought about stopping Pineapple Street when I was just a few minutes in. All the brand name dropping, the materialism. But I wanted to see if it was tongue in cheek or serious. In the end, I’m glad I gave it a chance, but it took me a long time to come around to the characters.
The story mainly tackles Sasha, a young woman who has married into an old money family. She doesn’t fit in, not used to a world of prenuptials, WASP traditions and casual prejudices. Woe betide the young wife who tries to change the familial home decorations! In some ways, the beginning reminded me of the story of Princess Diana at the royal family’s Christmas weekend. She’s always going to be an outsider. Her two sister-in-laws mistakenly call her the gold digger.
This almost felt like two different books. The beginning was all sarcastic humor, like the author wanted the reader to feel smug at the expense of the family, who are entitled, coddled and cocooned. It wasn’t until the book was over half done before she decided to give the sisters any sort of humanity that would make you care about them. And even then, there are still parts of their characters that had me cringing at their casual cruelty. As would be expected, everything works out as would be expected.
This book has gotten a lot of buzz. I guess, if you’re looking for a beach read this summer, it’ll easily fit that bill. Think of it like Crazy Rich Asians for the WASP set. But this is not a family drama that will stick with you after you finish it.
I listened to this and Marin Ireland narrated. She did her normal fine job.
Profile Image for mark monday.
1,794 reviews5,818 followers
March 21, 2024
summary: rich New Yorkers do boring things and think boring thoughts; a reader is likewise bored.

I thought I had ordered a 4-star eclair, delicious and decadent and made with a certain level of skill and authenticity. The dish arrived and it was a doughnut. But it had a dazzling exterior, colorful and vivid, and so I thought, okay this is a doughnut but that coating really catches the eye; perhaps this will be a 3-star doughnut at least? I took a bite and it was on the dry side, unremarkable, the whole thing was not remotely interesting but it was edible at least, inoffensive. Ok, a 2-star dish, fine. But then the next morning... the stomach ache! For such an insipid meal, it turned out to be nauseating to think about afterwards. Ugh, I particularly dislike experiences that are even worse to remember the day after. Especially when there is so little to actually contemplate... 1 star!

Remind me to never follow the New York Times' book recommendations. I should have known better just by reflecting on their daily recommended recipe, which usually starts my day off with a sneer. So basic. I mean really: chicken with potatoes... pasta with broccoli... one-pot spaghetti... eggs steamed in a microwave. Anyway, there is a certain bougie woke crowd to whom NYT book reviewers appear to cater: affluent, self-satisfied liberals who require the entertainments they consume to mirror the opinions they hold, reading moralistic tales lacking any flair or technique but that come outfitted, sack-like, with the most au courant of progressive ideologies. Their bog-standard virtues signaled, oh so strenuously. And so it is with Pineapple Street, despite its eye-catching exterior. Self-impressed and scolding, faddish in its politics, inanely virtue-signalling, zero style, shallow themes, predictable plot, dull characters. A null. Literally inspired by a NYT profile of young one-percenters who are redistributing their riches. Inspired by some fluff article... no surprise there. Apparently written in a mere four months; also no surprise.

I'm a class-focused progressive but that didn't help with digesting this book. I prefer food with spice. The novel depicts class tensions in the blandest and most uninteresting way imaginable; the taste was so blah. I like mayonnaise and syrup and vanilla is great too. But a whole dish composed of those ingredients is a horrible idea. No matter how bright the food coloring is that has been added to tart it up.

It was disheartening to learn that the chef in question is a leader in her field. An executive editor and vice president at Knopf! Good grief! To think that she is in a position to encourage the creation of even more flavorless dishes.
Profile Image for Ceecee.
2,446 reviews2,057 followers
August 14, 2022
‘Money, money, money
Must be funny
In a rich man’s world’ …. and the Stocktons have plenty of it. The matriarch and patriarch are Tilda and Chip, let’s just describe them as powerhouses with Tilda having an obsession with tennis and tablescapes, whatever that is! Darley their eldest daughter passes up her inheritance for love of Malcolm and motherhood.
Sasha marries in and comes from much humbler origins; she and Cord live in a four storey limestone on Pineapple Street that belongs to Tilda and Chip and they are NOT allowed to change a thing. Sasha doesn’t fit in and no matter how hard she tries she cannot penetrate the close family unit. Then there is the youngest, Georgiana, utterly coddled and totally spoilt but maybe, just maybe there’s hope for her.

This is a very incisive character driven study which shines a spotlight on a life of indulgence especially via the female line of the Stockton family. Tilda focuses on her favourite sport and shopping and simply airbrushes anything unpleasant and surely has to be the cause of so much dysfunction and tension! They are a strong unit probably because of the iron clad control and it’s no wonder Sasha finds it all very bewildering and although you wish she wouldn’t try so hard, she is genuinely likeable. On several occasions I want to yell at Cord for his words and actions and there’s even a bit of fist clenching from me!!

The character studies are excellent you realise beneath surfaces some are really messed up as you view their life and loves, their ups and downs. The story is told via Darley, Sasha and Georgiana and the three female voices seem very separate, even disparate but that is entirely the point as they have learn to plough their own furrow. You witness hurt, pain, sadness, hypocrisy and joy all told with humour and dry wit. It gets very lively when Darley’s children Poppy and Hatcher (???) are around as they are so funny!

It’s not especially fast of pace but it is an easy read and a good one at that. There are some are some uncomfortable moments especially around their enormous wealth but the author counterbalances that well with the developing storyline putting things into some kind of perspective.

I really like how it ends and overall enjoy spending time in and around Pineapple Street in Brooklyn Heights.

With thanks to NetGalley and especially to Random House U.K./Cornerstone for the much appreciated arc in return for an honest review.
Profile Image for Hannah Kelly.
369 reviews108 followers
March 26, 2023
Wow. I seriously worry for the future of books if this is what now passes for serious literary fiction. This was anything but. I definitely agree that the main reason this has become a critical darling is due to the author’s connections because frankly, this book isn’t good and it’s kinda amazing to me that someone who is an editor for a major publishing house is such a subpar writer. So much of the writing was not only cringe, it was outright crude and crass. The characters were unlikable and lacked any real values. Far from giving any type of insight on the moral nuance of the very wealthy, this book was just filled with stereotypes about rich people. It felt like a book written about rich people by someone who thinks they know all about rich people by having watched reality TV. I’m not saying that there aren’t some very interesting statements that can be made about class, wealth, socioeconomic status, etc. Many authors do these topics extremely well and when done well it can be revelatory. But this book was so surface level it provided zero insight and didn’t give any new perspective. I also really felt like it was super cheap of the author to sprinkle in buzz-worthy topics like racism, sexism, the shrinking middle class, etc. without actually even bothering to discuss these issues or have anything meaningful to say about them. It seemed like she was just doing it to get “woke” points rather than actually trying to make any actual statement. Overall, I’m so glad this was a library book and I didn’t pay money for it. This is prob the worst book I’ve read all year.
Profile Image for Lisa.
910 reviews
August 27, 2023
This was a DNF for me unfortunately I was looking forward to reading this but it was an unrealistic plot line ,characters were awful & how can a character not know that UAE 🇦🇪 is not a country please.
Profile Image for Jonetta.
2,386 reviews1,195 followers
August 4, 2023
the setup…
Welcome to the Stockton family, an old-money member of the one-percenters, living in a coveted Brooklyn community with fruit named streets. Chip and Tilda own a large home on Pineapple Street and have three children. Darley is their oldest, married to Malcolm and they are parents of Poppy and Hatcher. Cord is the only son and is married to Sasha who comes from a Rhode Island middle class family. Georgiana is the youngest who works for a non profit and struggles to connect with her parents’ world but finds it equally difficult to separate herself from it.

the heart of the story…
Darley, Sasha and Georgiana provide the narratives and they offer three unique insights into the Stockton family world. Darley had a highly successful career at Goldman Sachs before she threw the towel in after she became pregnant with her second child. What’s remarkable about her is that rather than ask Malcolm to sign a prenup, she gave up her inheritance (which will ultimately go to her children). She sees the world she was raised in with incredibly clear eyes, understanding the realities of the class system and navigates it extremely well without disturbing either side. Georgiana likes to think of herself as above the system, one with good values and a sense of fairness but finds herself in a relationship that speaks otherwise. While she may see herself this way, she’s so much a part of that world she's viewed by those on the outside of it as its biggest example. Sasha provides the most illuminating view as she valiantly tries to fit in with the family until she realizes the futility of it. It’s even more difficult when she and Cord move into the Pineapple Street house and can’t change a thing about it.

the narration…
Ireland delivers a strong performance, giving distinctive voice to three very well developed and unique characters, as well as the society driven Tilda. Her storytelling was compelling as she shifted seamlessly between the mindsets of the three points of view. This story is served best on audio!

the bottom line…
I expected a story that would shine some light on the world of people like the Stocktons. What I didn’t expect was how insightful and relevant it would be in understanding some of the current world issues we are now in the midst of and struggling for reckoning. The psychology and culture is deeply ingrained through generations. Tilda is the stereotypical character we imagine who embraces the trappings of the old-money world (think Emily Gilmore with far less skills); Darley and Georgiana know that there’s something fundamentally wrong with the growing chasm between the haves and have nots but both approach their ideas of the solutions very differently. Sasha provides the most objective view, coming into the family with little bias that changes dramatically as she comes frustrated with her failure to be accepted. This is a far more complex story than is presented. You just have to listen for it.

Posted on Blue Mood Café
Profile Image for L-J Johnson.
770 reviews5 followers
April 13, 2023
I'm trying to think of how to write a reasonable and intelligent review of this book, but I don't think I can; I hated it that much. It's super buzzy right now, lots of high stars, a celebrity Book Club pick, and come on, look at that great cover - it's got to have something going for it, right? Nope, not in my opinion. It's a blandly written boring story about an obscenely wealthy group of mid-20s- to mid-30s-year-olds, primarily a trio of siblings. There is some extremely mild skewering of the 1%, mainly in the stereotype of the mother, but let's call this what it is - a defense of the ultra-rich written by a publishing world bigwig. Probably everyone was afraid to tell this powerful woman how awful her book is. Even more offensive than the slathering love of the characters was the occasional dip into some "woke" issue, with absolutely no insight or depth -- just the worst of all possible virtue signalling. This book is so out-of-touch it's astounding; so much white privilege drips from it. Jackson has some incredible authors as clients - Cormac McCarthy, Chris Bohjalian, Emily St. John Mandel - and she clearly learned nothing from brushing up against their talents. I truly don't understand how something so wrong-headed was published, especially since the publishing industry is struggling to correct its generations of not supporting or printing the works of authors from marginalized populations.
There. Rant over. Now I have to go take a shower and wash away this experience.
Profile Image for NILTON TEIXEIRA.
1,113 reviews497 followers
March 25, 2023
4 stars for the witty writing and concept, but ,for the lack of depth, 3 stars seems reasonable.

(Below is a repeat of my reading updates - I didn’t feel like elaborating)

This was entertaining but quite pointless. But I have to say that the writing is quite good, especially the humour.
I will take this one as a good break from crime fiction or heavy topics.
This is an easy and fast read.
But seriously, there is nothing remarkable about this book.
The ending was very unsatisfying.
The audiobook is an excellent option, but I decided to stick to the book, as I read faster and I did not want to ruin a perfect narration by speeding up.

The author happens to be the vice-president and executive editor of Knopf Doubleday and this is her first novel.

Hardcover: 303 pages
Ebook (Kobo): 274 pages (default), 85k words
Audiobook narrated by Marin Ireland: 8.5 hours (normal speed)
Profile Image for Thomas.
1,703 reviews10.7k followers
May 12, 2024
Three stars feels a bit generous but, anyway, I thought this book was just okay. It follows the wealthy white Stockton family and three specific women within this family: Darly, the oldest daughter who was born with money but gave it up when she married her wealthy but not as wealthy husband, Sasha, who grew up middle class and married into the Stockton family, and Georgiana, the youngest daughter who works at a nonprofit and may develop a conscience about whether she should keep her trust fund or not. The three navigate romantic, financial, and familial conflicts throughout the book.

To start with the positive, I thought this book was mildly entertaining. I wouldn’t say the writing was of super high quality or the plot was one of the most immersive I’ve read this year, but I wasn’t bored reading it, could tell our three main protagonists apart from one another, and discerned that each of the three did have recognizable growth arcs by the end of the book. The cover and popularity of the book motivated me to read it and I didn’t hate the book.

Still, I found the book on a whole rather average. As stated earlier the writing wasn’t remarkable even though it wasn’t awful either. The characters all grew, but not in particularly groundbreaking ways. The book on a whole was predictable, though perhaps that’s the intended vibe. The one major thing I had issue with, which is why three stars feels generous, is that one of the characters decides to become a philanthropist by the end of the novel and the author doesn’t really acknowledge the problematic elements of rich white people engaging in philanthropy. The author seems to frame this character’s philanthropy as unilaterally positive, which ignores the white savior elements of a white woman still having the power to dictate what money goes to where and more, instead of thinking more critically about mutual aid, redistribution of wealth on a broader scale, etc.
It was alright! I wouldn’t recommend it necessarily but if you want a very casual book to pass the time, Pineapple Street may work.
Profile Image for Jillane.
122 reviews8 followers
February 13, 2023
First, I did like the author’s writing style and found it easy to be immersed in the world she created. However, this novel was very character-driven and I didn’t care that much about any of the characters. More than anything, I really really didn’t like the way that wealth and class were explored. I think maybe I’m not that interested in reading about super rich people, even if they’re fictional, especially if ultra-wealth is only going to be criticized in extremely superficial ways. This was not for me!

Thank you to NetGalley and the publishers for the ARC!
Profile Image for Emily Stevens.
639 reviews5 followers
March 10, 2023
1.5 stars

Wow, I honestly can't believe all of the glowing reviews for this book. I was beyond disappointed.

This is a story of rich white people written by a rich white publishing executive. I'm not sure why I expected something different.

Nothing happens in this book. Seriously, nothing. It's just a boring description of their overly privileged lives. Even Sasha, the 'outsider' comes from the Rhode Island Coast.

To me, this book took up space in the reading world that would have been better served by a BIPOC, LGBTQIA+ or diverse author with a debut novel that actual accomplishes something. I apologize for the blunt review but this book really got under my skin.

This gets more than 1 star only because the writing was flawless, however, I'd expect nothing less from a publishing exec.
Profile Image for Suz.
1,381 reviews739 followers
March 1, 2024
Often I will read a book due to its New York setting, and this was one of those times. The audio was a great experience, with the many characters easily discernible. I do believe audio narration is an art, and I love when the performer gets it right. Marin Ireland, well done!

The Stockton family are wealthy, of the old money kind. Each sibling is well presented, as are the parents and the spouses. The WASP ideal was evident and named many times. Each sibling has their own ideas about parenthood, employment, their privilege, their place in society, what to do with their wealth, and how to go about the marital prenup. This is serious stuff when these guys are seriously wealthy.

I thought I may become frustrated if the territory meandered into snobbish territory, but surprisingly it did not. The tennis loving matriarch had her moments, she didn’t seem overly interested in her children, and cheekily lied on her newsletter style Christmas update espousing the generosity of their grandparental duties. They didn’t babysit!

Georgiana, the youngest, fell in love with the wrong person with hard consequences, leading her to question her insane wealth and desire to do something good by it. She did not even know what her bank balance was, or check her statements.

Sascha married in, she was not poor, she was middle class, she literally had to explain this to the family, and again, she seemed remarkably able to do so without losing it. Class clearly is what this is all about, though in a subtle way. I wasn’t put off or feeling unjust. It somehow worked as a discussion on the unfathomability of other families having a peep in. Coined the Gold Digger (GD) by her sister in laws, she showed a remarkable ability to put up with it all.

These folk are the one percenters, who certainly have some weird relationships (Sasha’s husband rubbing his mother’s feet?) but are fiercely loyal. Such a funny book which felt like it was not about a real lot, but the star of the show were the characters, and that’s what I love in my fiction.
A clever debut which showed excellent writing and a fresh idea.

A completely different way for me to travel to New York.
Profile Image for Ellery Adams.
Author 69 books4,768 followers
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March 22, 2023
This is a character-driven escapist read about a family of wealthy New Yorkers and the people who marry into the family. It's fun and voyeuristic because the family is one percenters, which means the expenditure and entertainment is as over-the-top as you'd expect. Most of the characters are unlikeable at the beginning but some learn lessons as the book progresses, and the reader is left feeling hopeful. A perfect palate cleanser between heavier reads.
Profile Image for Dominique.
60 reviews18 followers
March 15, 2023
It started fine and ended awful, in writing quality, story, and message. I think it thinks it’s An Important Social Commentary? But there’s NOTHING smart or incisive or new that it says about money, or class, or even Brooklyn Heights. It’s like a Portlandia sketch of rich people trying to prove to each other they’re self-aware, as they play a truly staggering amount of tennis in exclusive clubs. (Was this book sponsored by Wilson?) There are long passages that sound like they’re lifted wholesale from amateur TikTok explainers (“did you know that wealthiest 3 men in America earn more than the entire bottom half?” “Really? WOW!”)

It’s like if someone tried to create a portrait of the wealthy in New York based exclusively on Sex and the City/Gossip Girl caricatures. The one or two nonwhite characters are Asian and we know that because they are announced as such, and for NO other reason- there is zero cultural specificity (which isn’t even accurate among the super wealthy in New York; wealthy kids of color are players in this space, too, but you’d never know it from reading this book) This omission palpably feels like the choice of someone who KNOWS they lack the range or the curiosity to write from any perspective than THE most unexamined, anodyne whiteness.

(The audiobook narrator doesn’t help things by being FAR too singsong. The fact that the narrator uses the same tone of voice for the 6-year-old and the 20-something is telling. Every character sounds like that Cecily Strong “drunk at the party” girl.)

I’m very sorry I fell for the “hot new book” hype, I could have spent my time reading something with a discernible point of view, care for craft, and/or plot worth getting invested in.

I feel swindled the way I did after Black Buck. A+ marketing, D+ book.

Take it from me, give it a miss.
Profile Image for Taury.
899 reviews203 followers
April 22, 2023
Pineapple Street by Jenny Jackson is a book about money. The worst thing than too much money is being poor.

I have yet found my book of the month. Anything about pretentious, upper class, self serving humans and young adults is definitely not my thing.
Profile Image for Gail.
1,178 reviews426 followers
April 29, 2023
I loved this book. See also these two graphs from the NYT Review of it:

It’s no small thing to ask a reader in 2023 to empathize with characters who are not only exceedingly wealthy but generationally exceedingly wealthy, and who say things like “Oh no! I left my Cartier bracelet in Lena’s BMW and she’s leaving soon for her grandmother’s house in Southampton!”

This is the challenge Jenny Jackson has set herself, and not only does she succeed in getting us not to loathe the Stocktons, the family at the center of her debut novel, “Pineapple Street,” but she even succeeds in persuading us to love them. A little bit. Even if … OK … a little bit against our will.


I especially loved any time Tilda (the matriarch of the Stockton family) and Cord (the Labrador Retriever of her son) showed up on the page. They were the characters who made me laugh most.
Profile Image for Katerina.
117 reviews11 followers
September 28, 2022
An easy read, but a forgettable one. The plot is quite loose, following the lives of three über wealthy women in New York (two by birth, one by marriage) navigating family dynamics, their social environment and many quintessentially first world problems. It was hard to warm up to any of the characters, not because they were annoyingly out of touch with the real world and egocentric (there are plenty of novels with similar casts of characters that do this excellently or, let's say, Gossip Girl), but because they are hastily written - like a faint outline of how a specific type of person would be. The writer tells us how we should perceive the character based on their family members characterization of them and reminds us when a specific behavior is WASPy (show, don't tell!)..
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