book review for pineapple street

Big Money, Big Houses and Big Problems in Brooklyn Heights

In Jenny Jackson’s debut novel, “Pineapple Street,” readers get a tour of a world they might learn not to envy by the end of the book.

“Pineapple Street” is set in the elegant world of Brooklyn Heights. Credit... Bianca Bagnarelli

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• March 3, 2023
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PINEAPPLE STREET, by Jenny Jackson

A certain Great American Novelist known for writing about the very rich was of the opinion that they were different from you and me. They were, and a century later, they still are, and we still want to read about them, for reasons both obvious (mainly to do with schadenfreude) and less so (mainly because, at the end of the day, we may not be so different at all).

Still, 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.

This is an unabashedly old-fashioned story involving wills, trust funds, prenups and property — lots of property, and so much of it in a single refined corner of Brooklyn that family members (Chip and Tilda Stockton and their adult children: Cord, Darley and Georgiana) refer to the mother ship among their family holdings as “the limestone.”

The Stocktons are a real estate family, but not like a real estate family from, say, Queens, who might delineate success by putting their family name on everything in sight. Instead, they’re under the radar, happy to be known by people they have always known in Brooklyn Heights, the Hamptons and at their clubs, where they play tennis constantly (and competitively) against one another.

Tilda is “of a generation that despised difficult conversations and shut down at the slightest hint of conflict or unpleasantness,” but that reticence has also been passed down to her daughters, Darley (a brilliant businesswoman now at home with her children) and Georgiana (who works, without much engagement, at a philanthropic organization located in a Brooklyn mansion). Tilda is that frustrating mix of a person who will move out of “the limestone” after many decades in order to offer it to her son, Cord, and his new wife, Sasha — who is from Rhode Island and emphatically not the Newport end of the state, either — but still police her daughter-in-law’s “tablescape” arrangements and forbid her to throw away so much as a trophy from outgrown and abandoned bedrooms when she comes over for dinner.

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PINEAPPLE STREET

by Jenny Jackson ‧ RELEASE DATE: March 7, 2023

A remarkably enjoyable visit with the annoying one percent, as close to crazy rich WASPs as WASPs can get.

Money makes the world go round, particularly the world of an elite Brooklyn family.

"On good days, Sasha could acknowledge how incredibly lucky she was to live in her house. It was a four-story Brooklyn limestone, a massive, formal palace that could have held ten of the one-bedroom apartments Sasha had lived in before. But on bad days...." As Sasha finally admits in a gloves-off monologue following a gender reveal party gone awry, on bad days, it's "a janky Grey Gardens full of old toothbrushes and moldy baskets." A wealthier cousin of Cynthia D'Aprix Sweeney's The Nest , Knopf editor Jackson's fiction debut is a comedy of manners charting the fates of the Stockton siblings and their spouses, circling around the house where they grew up in Brooklyn Heights, now inhabited by Cord and his wife, Sasha, who is referred to as the Gold Digger by Cord's sisters, Darley and Georgiana. That's unfair, though: Sasha signed a prenup. Meanwhile, Darley and her husband, Malcolm, a Korean American aviation-industry analyst who did not sign a prenup, are living off their own money as Darley fights the tedium of the entitled mommy lifestyle. Georgiana, much younger than her siblings, still single, is considered the do-gooder of the family because she works for a nonprofit, where she becomes involved in a passionate and very ill-advised relationship. From the opening scene, where Sasha's mother-in-law shows up to dinner with an entire replacement menu and a revised "tablescape," Jackson has a deft hand with all the passive-aggressive interactions that are so common in family life, perhaps particularly in this socio-economic stratum. She knows her party themes, her tennis clubs, her silent auctions, and her WASP family dynamics. Rich-people jokes, cultural acuity, and entertaining banter keep this novel moving at a sprightly pace as the characters learn their lessons about money and morals, though some of the virtuous reform seems a little much.

Pub Date: March 7, 2023

ISBN: 978-0-59-349069-3

Page Count: 320

Publisher: Pamela Dorman/Viking

Review Posted Online: Dec. 13, 2022

Kirkus Reviews Issue: Jan. 1, 2023

LITERARY FICTION | FAMILY LIFE & FRIENDSHIP | GENERAL FICTION

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New York Times Bestseller

by Kristin Hannah ‧ RELEASE DATE: Feb. 6, 2024

A dramatic, vividly detailed reconstruction of a little-known aspect of the Vietnam War.

A young woman’s experience as a nurse in Vietnam casts a deep shadow over her life.

When we learn that the farewell party in the opening scene is for Frances “Frankie” McGrath’s older brother—“a golden boy, a wild child who could make the hardest heart soften”—who is leaving to serve in Vietnam in 1966, we feel pretty certain that poor Finley McGrath is marked for death. Still, it’s a surprise when the fateful doorbell rings less than 20 pages later. His death inspires his sister to enlist as an Army nurse, and this turn of events is just the beginning of a roller coaster of a plot that’s impressive and engrossing if at times a bit formulaic. Hannah renders the experiences of the young women who served in Vietnam in all-encompassing detail. The first half of the book, set in gore-drenched hospital wards, mildewed dorm rooms, and boozy officers’ clubs, is an exciting read, tracking the transformation of virginal, uptight Frankie into a crack surgical nurse and woman of the world. Her tensely platonic romance with a married surgeon ends when his broken, unbreathing body is airlifted out by helicopter; she throws her pent-up passion into a wild affair with a soldier who happens to be her dead brother’s best friend. In the second part of the book, after the war, Frankie seems to experience every possible bad break. A drawback of the story is that none of the secondary characters in her life are fully three-dimensional: Her dismissive, chauvinistic father and tight-lipped, pill-popping mother, her fellow nurses, and her various love interests are more plot devices than people. You’ll wish you could have gone to Vegas and placed a bet on the ending—while it’s against all the odds, you’ll see it coming from a mile away.

Pub Date: Feb. 6, 2024

ISBN: 9781250178633

Page Count: 480

Publisher: St. Martin's

Review Posted Online: Nov. 4, 2023

Kirkus Reviews Issue: Dec. 1, 2023

FAMILY LIFE & FRIENDSHIP | GENERAL FICTION | HISTORICAL FICTION

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by Kristin Hannah

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THE NIGHTINGALE

by Kristin Hannah ‧ RELEASE DATE: Feb. 3, 2015

Still, a respectful and absorbing page-turner.

Hannah’s new novel is an homage to the extraordinary courage and endurance of Frenchwomen during World War II.

In 1995, an elderly unnamed widow is moving into an Oregon nursing home on the urging of her controlling son, Julien, a surgeon. This trajectory is interrupted when she receives an invitation to return to France to attend a ceremony honoring  passeurs : people who aided the escape of others during the war. Cut to spring, 1940: Viann has said goodbye to husband Antoine, who's off to hold the Maginot line against invading Germans. She returns to tending her small farm, Le Jardin, in the Loire Valley, teaching at the local school and coping with daughter Sophie’s adolescent rebellion. Soon, that world is upended: The Germans march into Paris and refugees flee south, overrunning Viann’s land. Her long-estranged younger sister, Isabelle, who has been kicked out of multiple convent schools, is sent to Le Jardin by Julien, their father in Paris, a drunken, decidedly unpaternal Great War veteran. As the depredations increase in the occupied zone—food rationing, systematic looting, and the billeting of a German officer, Capt. Beck, at Le Jardin—Isabelle’s outspokenness is a liability. She joins the Resistance, volunteering for dangerous duty: shepherding downed Allied airmen across the  Pyrenees to Spain. Code-named the Nightingale, Isabelle will rescue many before she's captured. Meanwhile, Viann’s journey from passive to active resistance is less dramatic but no less wrenching. Hannah vividly demonstrates how the Nazis, through starvation, intimidation and barbarity both casual and calculated, demoralized the French, engineering a community collapse that enabled the deportations and deaths of more than 70,000 Jews. Hannah’s proven storytelling skills are ideally suited to depicting such cataclysmic events, but her tendency to sentimentalize undermines the gravitas of this tale.

Pub Date: Feb. 3, 2015

ISBN: 978-0-312-57722-3

Page Count: 448

Review Posted Online: Nov. 19, 2014

Kirkus Reviews Issue: Dec. 1, 2014

HISTORICAL FICTION | FAMILY LIFE & FRIENDSHIP

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Book review: Pineapple Street is a witty debut about old money with a hasty ending

Pineapple Street By Jenny Jackson Fiction/Cornerstone/Paperback/342 pages/$25.92/Books Kinokuniya 3 stars

In the prelude of editor Jenny Jackson’s debut novel Pineapple Street, a character rushes out of a coffee house after uttering the line: “Oh, no! I left my Cartier bracelet in Lena’s BMW and she’s leaving soon for her grandmother’s house in Southampton!”

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The Bookshelf

BOOK REVIEW: Pineapple Street by Jenny Jackson

Take a trip to brooklyn heights where old money and family drama prevail..

I enjoy reading about family and the drama that families engage in behind closed doors, and Pineapple Street was a perfect combination of drama and extravagance. After I finished the book, I looked at some reviews, which I do sometimes, just to see what others thought of it while I process my own thoughts. I read one that said the reader didn’t like this book because “nothing happened.” I will always respect people’s personal opinions on books as long as they are not rude to the author, but I found this to be an interesting thought.

If you are looking for action/adventure or serial killers or even ghosts or zombies, you will definitely not find them on Pineapple Street. What will you find on Pineapple Street you may ask? You will find a slightly dysfunctional family that ebbs and flows through life under the protection and influence of having generational wealth on their side. However, money doesn’t solve all problems, can’t cure grief, and hasn’t yet countered ignorance.

The plot is driven by the characters, which again could be why some don’t feel like anything happened, but I’m going to argue that there are some very poignant and powerful moments that occur in these characters’ lives. The Stockton family comes from old money and consists of aging parents, Tilda (who is obsessed with tennis and probably should have been an interior designer or event planner in a middle class life) and her husband Chip (who, you know, runs a New York empire like all rich people in books do). The majority of the focus revolves around their three adult children, Cord, Darley and Georgiana.

There were things you could do with family that you just couldn’t do with friends: You could let them see you wearing the same outfit three days in a row. You could invite them over for lunch and then mostly ignore them as you finally got off hold with the internet provider. You could have an entire conversation while wearing Crest Whitestrips.

Multiple points of view help to jump between Darley and Georgiana, but instead of Cord, it is his new wife Sasha who gets her own chapters. This was a very important element in the global perspective of the book. Why, you ask? Well, because Sasha doesn’t come from the privilege and money that Cord’s family does. There are things she doesn't understand when it comes to behaviors and priorities of the others, and she has to contend with the idea that she is a “Gold Digger” and judged by her sisters-in-law while she fights to be accepted. Cord , of course, is completely oblivious to the actions of his family, because wealth is his life and his family has always been this way. 

While we get to follow Sasha’s struggles to fit in and be accepted, we also follow Darley who has also married someone not of old money. There are aspects of this relationship that are different from that of Sasha and Cord, and I really enjoyed watching the similarities, differences and how their experiences parallel. Darley and her husband, Malcolm, have the only children in the group and their two kids are totally the comic relief. Kids don’t understand society’s class systems, expectations and what it means to be privileged when they are young. They are simply spunky, sassy, no-filtered kids obsessed with death, and I loved their authenticity. When they got kicked out of the pool, I couldn’t help but laugh out loud.

As all the characters are dealing with marital and family relationship struggles, it is Georgiana that suffers the most throughout the story. As the youngest of the three Stockton children and the one still single, she is the one who makes some not great decisions, but also suffers the most. All the characters’ lives intertwine with each other to different degrees and at different levels. When Georgiana suffers a traumatic loss, her inability to cope and a family that isn’t very in tune to emotions struggle to know what is going on. It is a powerful element to the story. So yes, stuff happens in this book, but it is how the characters individually react to the most mundane to the traumatic that propel it forward.

There is nothing quite like family, and clearly money doesn’t buy happiness. Those thematic notions are clear throughout. However, the importance of “keeping up appearances” and the “wealthy should marry the wealthy” are ideals that are so ingrained in the family that it’s hard to change that mindset.

There is also plenty of tennis which fits with the notion that “competition was their family love language.” 

Where does this land on my bookshelf?

I’d place it on the middle shelf…but at the top of it. I really liked this book and reading about families always intrigues me. With this one, there is a societal element as well in how people are perceived and perceive others when it comes to wealth. Social status is important and “family infiltration” is a real thing. This is a perfect summer read, even though there are a few heartbreaking moments, but that’s life, right? It’s not all unicorns and rainbows - no matter how much money you have. If you haven’t read it yet, definitely add it to your TBR!

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book review: Pineapple Street by Jenny Jackson

Overview: The Stockton family has long called the fruit streets of Brooklyn home, and even as their children grew up and moved out, they stayed nearby. Pineapple Street  looks at a period in the wealthy family's life from three distinct perspectives. We experience the events of the story through youngest daughter, Georgiana, who's in her early twenties and the baby of the family, Darley, the oldest of the daughters, and Sasha, the brother's new wife who sees all the happenings of the Stockton's lavish lifestyle as a bewildered outsider. Overall: 5

Characters: 5 While we only have 3 point of view characters, all of the Stocktons get rich portraits drawn over the course of the book. Having these three different vantage points is also what makes the story so fascinating. It seems intentional and is impactful that Jackson chose to tell the story through the points of view of the three younger women in the family, and they do exhibit the most growth as the book progresses. 

Sasha always feels like the outsider. She grew up middle class in Rhode Island and often feels like she came from a different planet entirely than the Stockton household where each kid inherited tens of millions of dollars when their grandparents died and high society is their second language. She's the grounding force that puts into perspective the outlandish issues the family creates. Sasha also quickly bonds with Darley's husband Malcom as the only other outsider who doesn't understand the strange intricacies of their life. Sasha runs up against many pain points as she strives to find allies within the family as Darley and Georgiana are convinced that she's just a gold digger. As Sasha starts her new life with her husband, Cord, including moving into the Stockton's family home on Pineapple Street, she'll have to figure out how to claim her own space is a family devoted to keeping things the same.

Darley is a few years older than Sasha and has two kids. Much of Darley's story centers around her struggles as a stay at home mom questioning her loss of identity and income potential. The question of inheritance is also centered in Darley's story as she's chosen to forgo access to her trust and pass it directly to her children so that her husband, Malcom, didn't have to sign a prenup. Because she became a stay at home mom after her second child, though, that leaves her in the tough position of not having an income of her own. While Darley has grown up in her parents' New York society world, she still doesn't have an effortless experience navigating the politics of private elementary school and what happens when a seemingly steady single income vanishes overnight. 

Finally, Georgiana is in her early twenties and has never known a world beyond her privileged bubble. She lives in an apartment she bought with a down payment from her trust, she works a low paying job at a nonprofit with no regard for what her salary even is, and she's generally pretty self absorbed, something Sasha is always keen to point out. Being the youngest, Georgiana also follows the greatest evolution over the course of the novel. She meets a few people who make her seriously question her life trajectory and belief systems, looking beyond her tennis ranking for the most important things in life for the first time. Over the course of the novel, Georgiana questions everything she's ever known about her family and the world. 

Plot: 5 The multiple perspectives keeps the book moving as we get increased tension from knowing sides of the story that the other point of view characters we read about are oblivious too, so there's plenty of foreshadowing and extra painful miss communication. The tension and pacing are incredible, especially considering how slow and tedious some literary fiction books dealing with similar themes have been. This book is certainly looking for the line right between literary and commercial and does a beautiful job finding it. I have to wonder if this is owing to the fact that the author is an executive editor at Alfred A. Knopf. The book certainly has a sense of being aware of its readers need for drama and intrigue, and it's tightly plotted. Somehow, even in this wild family, there was only one point that felt like it pushed the details of the scene to a bit of an over the top place. 

Writing: 5 I couldn't put the book down from the very first page. The book hits the right notes of having a compelling plot and characters that you become quite invested in despite all of their flaws and lack of a connection to earth. At the end of the day, though, the book is truly about cutting through the noise to realize there are very few things that truly matter in the end, and family, even a dysfunctional one, is worth more than any divides that come between them from money, status, or perceptions.

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Pineapple Street Book Club Questions and Discussion Guide

If you enjoy peeking into the messy lives of the ultra wealthy, Pineapple Street is a perfect match for you and your book club. Pineapple Street examines sibling cliques, WASP guilt, and the power money has to shape a person’s identity for better or worse – all inside the shiny bubble of east Manhattan. 

Our discussion guide for Pineapple Street will help you find the deeper message under this novel’s witticisms. First, we’ve provided a synopsis of Pineapple Street to help you keep track of all that family drama. Next, we’ve provided 10 Pineapple Street book club questions. Talk them over with your book club members, and you may be surprised by the different perspectives in your group. Last but not least, we’ve pulled a few quotes from Goodreads book reviews to spice up your conversation. (Not everyone is a fan of this bestselling novel!)

And for more upper class escapism , read to the end of this guide for a list of 3 suggestions of books like Pineapple Street!

(This article contains affiliate links. This means that if you choose to purchase, I’ll make a small commission.)

Pineapple Street Synopsis

(We always chose to provide the publisher synopsis because we feel that it’s worthwhile to discuss whether the official book description actually squared with your experience of the book.)

Pineapple Street , Jenny Jackson

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.

10 Pineapple Street Book Club Questions

These questions have been tailored to this book’s specific reading experience, but if you want more ideas, we also have an article with 101 generic book club questions .

• The Stockton children have an extremely close relationship, to the point that their partners feel excluded from their clique. Do you belong to any cliques that might make others feel excluded? How much do you value inclusion vs. preserving an inner circle of friends?
• Tilda’s talent for avoiding large emotional displays sometimes makes her children feel isolated. Yet, in other ways, Tilda has a strong presence as a mother: practicing sports, giving gifts, and throwing parties for her children.  Do you think Tilda is at fault for creating the emotional distance between herself and her children, or are the children also failing to understand their mother? 
• Early in the novel, Georgianna observes, “It was easy to say that money was the root of all evil, but so many of the things money could buy provided dignity, health, and knowledge.” Can you see ways that money has made you a better person? Can you imagine a system that allows money to do more good than harm to society?
• Although the house on Pineapple Street is large and decorated with expensive art and furniture, Sasha finds the house tacky and uncomfortable. How do you think the house symbolizes the conflict between the upper and middle class?   
• Sasha compares her peaceful relationship with her husband, Cord, to her passionate relationship with her first boyfriend, Mullin, and reflects that “she wanted someone who loved her but didn’t need her.” Do you think Sasha was wise to change what she wanted out of a relationship? What might she sacrifice by choosing a partner like Cord instead of Mullin?
• Georgianna consents to continue her relationship with Brady after discovering that he’s married to another woman. Do you think Brady is exploiting her, or does her consent make her equally responsible for the affair? Do you believe Brady when he says he loves Georgianna?
• After Malcom was fired, Darley chooses to conceal that fact from her family for weeks, until Malcolm explains that the secret makes him feel like he’s only acceptable to the Stocktons because of his paycheck.  Do you sympathize with Darley’s desire to keep Malcolm’s situation secret? How does Darley make Malcolm feel valued in her family and how does she fail to do so?
• Curtis tells Georgianna that “income equality is the most shameful issue of our time.” Do you agree? What other issues might claim this title?
• Darley and Cord defend Georgianna’s bad behavior by claiming that she is only a child. Georgianna is twenty-six years old. Do you think their claim is valid? At what age can we expect people to start acting “adult”?
• When Cord returns home with Sasha to visit her family, he seems to fit right in with the her siblings and cousins. Why do you think Cord is so much more comfortable with Sasha’s family than Sasha is with the Stocktons?
• BONUS QUESTION: By the end of the novel, most of the Stocktons seem to be on a path to self-improvement and reconciliation. Which characters do you think are most/least capable of finding “happily ever after”?

Selected Reviews for Pineapple Street

(Use these selected Goodreads reviews to compare with your own experience of the book. Do you agree or disagree with the reviews?)

“The character studies are excellent. You realize, beneath the surface, some are really messed up as you view their life and loves, their ups and downs. 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 humor and dry wit.”  

“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 jargon 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.”

“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.”

“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.”

NEED BOOK CLUB IDEAS?

Use our guide to find dozens of book ideas for your group.

3 Books Like Pineapple Street

We’ve also got a book club guide for Lies and Weddings (by Kevin Kwan), which also features rich people problems.

The Dutch House , Ann Patchett

If you enjoyed the sibling dynamics in Pineapple Street, you’ll be sucked in by the brother-sister devotion in The Dutch House. Unlike the Stocktons, young Danny and Maeve are exiled from their lavish childhood home when their father marries a younger woman. Together they navigate a world where they feel out of place, comforting each other with memories of home that, over the years, transform into their own personal mythology. But when an opportunity to reclaim what they’ve lost arises, their devotion to each other and their past is put to the test.

Read this one for book club and use our Dutch House discussion guide .

The Interestings , Meg Wolitzer

Continue your exploration of money’s power to divide loved ones with The Interestings. This witty novel follows the lives of six teenagers who pledge their eternal friendship to each other inside a summer camp teepee. But when one of the teens grows into a cartoonist responsible for the creation of an iconic comic strip and an empire of franchised merchandise, fame and wealth threaten to make old friends unknowable.

The Seven Husbands of Evelyn Hugo , Taylor Jenkins Reid

A story that could be told by Tilda Stockton herself, The Seven Husbands of Evelyn Hugo follows an enigmatic Hollywood star as she recounts the sacrifices of heart and conscience that she made to succeed in a world where her appearance was constantly scrutinized. For years, she has played (and won) the fame game, but now she’s ready to reveal her most dangerous secret: the identity of her one true love. 

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Pineapple Street

57 pages • 1 hour read

A modern alternative to SparkNotes and CliffsNotes, SuperSummary offers high-quality Study Guides with detailed chapter summaries and analysis of major themes, characters, and more.

Chapter Summaries & Analyses

Prelude-Chapter 4

Chapters 5-9

Chapters 10-14

Chapters 15-20

Chapter 21-Epilogue

Character Analysis

Symbols & Motifs

Important Quotes

Essay Topics

Discussion Questions

Summary and Study Guide

Pineapple Street is a satirical exploration of the lifestyles of the mega-wealthy of New York City. Using elements of the family drama to criticize how inherited wealth foments structures of exclusivity, Jackson explores the perspectives of three female protagonists at varying stages of their lives. She bookends these perspectives with the point of view of Curtis McCoy , a wealthy young man who handles his own inherited wealth morally and responsibly. Pineapple Street blends a coming-of-age family drama with romantic comedy to create a social commentary on the ways in which wealth can either influence or inhibit personal growth in contemporary America.

This guide refers to the version of Pineapple Street published by Penguin Random House in 2023.

Plot Summary

The wealth of the Stockton family has its origins in real estate development and politics and has been passed down and built upon over the course of many generations. Thus, the Stocktons are members of an elite class of New Yorkers who can afford absolutely anything they may want or need. Tilda and Chip, the mother and father of the family, are sticklers for tradition. Their oldest daughter, Darley, is married with children. Their youngest daughter, Georgiana, is a shy, sweet tennis player who works for a non-profit organization. Their son Cord has recently married Sasha, who is an outsider to the wealthy world of elite New Yorkers.

Sasha comes from a middle-class family and grew up in Rhode Island before marrying into the Stockton family through Cord. Despite her new official status as a member of the Stockton family, she senses immediately that her presence is not fully accepted by Cord’s family members. She and her new husband live in his childhood home, a massive, historic house on Pineapple Street, located in the exclusive neighborhood of Brooklyn Heights. This house represents the Stockton family’s legacy and lineage, but for Sasha, living there is as uncomfortable as living in a museum. Tilda and Chip still own the house and allow Sasha and Cord to live there for free, which is a significant privilege. Even so, Tilda has stipulated that everything in the house must remain the same, so Sasha must relinquish considerable autonomy in order to live there. Sasha appreciates that Cord is loyal to his family, but she notices that he never defends her, especially against his sisters, who behave coldly toward Sasha. (Because Sasha took offense when presented with the standard Stockton pre-nuptial agreement, Georgiana suspects that Sasha is only interested in Cord’s money . Darley is only suspicious of Sasha because she knows so little about her.) Despite these social setbacks, Sasha works hard to ingratiate herself with Cord’s sisters.

Darley is happily married to Malcolm, a Korean American man who grew up in a middle-class home like Sasha but earned his way into wealthier circles through his intelligence, hard work, and passion for aviation. He travels extensively for work but is utterly devoted to his family. Although Malcolm was willing to sign the pre-nuptial agreement, Darley who told him not to and let go of her inheritance. Her portion of the Stockton fortune will go instead to her children. Thus, Darley chose love over money, which emphasizes her priorities and values. The Stocktons readily accept Malcolm because, despite his status as an outsider, he makes enough money to keep up with the Stockton lifestyle. However, when Malcolm is unfairly fired from his job merely for being associated with a colleague who made a critical error, Darley is forced to reckon with her lack of income and inheritance. She is also forced to acknowledge that the racism and nepotism that pervades the society of the super-rich has irreparably damaged her husband’s career path.

Shy and easily embarrassed, Georgiana is the youngest Stockton child at 26 years old, but her overprotective family treats her as though she is much younger. Georgiana’s life is fun but lacks meaning. Although she works for a non-profit organization, she has no intentions of building her job into a larger career. She lives in an apartment that her parents pay for, and her life is mostly focused on playing tennis and partying with her friends. Essentially, Georgiana is aimless, but because of her wealth, she has no need to build a more productive life for herself. Georgiana also has a crush on an older, more powerful man at work named Brady, but she is too shy to approach him. When Brady makes the first move and they become a couple, Georgiana is elated. However, she soon discovers that Brady is married, and Georgiana chooses to continue their relationship, turning what she sees as true love into a tawdry affair. When Brady dies in a tragic plane crash, Georgiana is deeply saddened and develops a pattern of self-harm.

Darley and Georgiana keep their personal problems a secret from their family, but they both confide in Sasha, who sees this as an opportunity to build friendships with her sisters-in-law. However, when she finds out that they believe she is a “gold digger,” she realizes that they only shared their secrets with her because they don’t care enough about her opinion to fear her judgment. When the rest of the family finds out what Georgiana has been going through, they become angry with Sasha for not telling them. Sasha is placed in a lose-lose situation. When Sasha’s father becomes seriously ill, she returns to Providence to be with her family. This necessary distance between her and the Stocktons helps her to rethink her priorities and decide how best to proceed with her relationship with Cord. When she learns that she is pregnant, she knows that it is all the more urgent for Cord to start defending her from his family’s criticism. When Cord comes to Rhode Island to be with her, she confronts him with the sticky reality of their socio-economic class differences. Although the conversation makes Cord uncomfortable, it is a necessary confrontation to improve their relationship.

Meanwhile, Georgiana decides that she must become a better person. She is not sure how to improve herself, but she finally realizes that her current lifestyle is meaningless. She admires Curtis McCoy, a former high school peer who gave up his own family fortune by creating a foundation with his inheritance money. Georgiana is inspired by Curtis’s actions and decides to do the same. This decision shocks the Stockton family, but it also has the ripple effect of making all the Stocktons think more deeply about the influence of their privilege and the ways in which privilege can prevent them from recognizing the realities of the world.

Meanwhile, Darley meets a wealthy man named Cy Habib who has major connections with Emirates Airlines. He gets along well with Malcolm, who also has a passion for aviation. Through Cy, Malcolm lands a dream job with Emirates Airlines. Cord and Sasha give the house on Pineapple Street to Darley and her family, which fulfills one of Darley’s dreams. When Sasha hosts a birthday party for Chip, a fire starts in the house. Although the house is saved, many of the Stockton artifacts are destroyed. Thus, as the Stocktons change for the better, so too does the physical manifestation of their family’s history: the house on Pineapple Street.

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Book Review: Pineapple Street

Here’s my book review for pineapple street by jenny jackson. don’t forget to leave a comment if you’ve read it too. (also, look for today's writing prompt at the bottom of this post.).

I thoroughly enjoyed this character-driven novel with incredibly engaging dialogue. I especially appreciated that it was hilarious, thought-provoking, and deeply emotional simultaneously throughout because it made the overarching storyline of the novel more realistic and intimate, making it easy to read.

Pineapple Street forces readers to confront social…

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2 novels to cure your winter blahs: Ephron's 'Heartburn' and 'Pineapple Street'

Maureen Corrigan

I met a good friend for dinner the other night and told her I was rereading Nora Ephron 's novel, Heartburn , which has just come out in a 40 th anniversary edition. " I'm so pissed off ," this friend said, echoing Meryl Streep 's words at Ephron's memorial service in 2012. "Why isn't she still here?"

My friend and I locked eyes over our margaritas and nodded. We didn't have to tick off all the ways we needed Ephron's tough wit to help us through things. It's sentimental to say so, but when such a beloved writer's voice is stilled, you really do feel more alone, less armored against the world.

I've read Heartburn three times since it came out in 1983. Some of its jokes haven't aged well, such as wisecracks about lesbians and Japanese men with cameras, but the pain that underlies its humor is as fresh as a paper cut. For those who don't know the novel, Heartburn takes place mostly in an elite Washington, D.C., world of journalists and politicians and is a roman à clef about the break-up of Ephron's marriage to reporter Carl Bernstein , of Watergate fame.

The year was 1979 and Ephron was pregnant with the couple's second child when she discovered Bernstein was having an affair with Margaret Jay, the then-wife of the then-British ambassador. In Heartburn , her character is famously skewered as: "a fairly tall person with a neck as long as an arm and a nose as long as a thumb."

Everyone who's read Heartburn or seen the movie — with Meryl Streep playing Ephron's fictional alter ego, cookbook author Rachel Samstat — remembers the climactic dinner party scene where Rachel throws a key lime pie at the face of her cheating husband. (In real life, Ephron poured a bottle of red wine over Bernstein's head.) It's as though Ephron, herself the child of two golden age Hollywood screenwriters, took one of the oldest clichés in comedy — the pie in the face — and updated it to be a symbol of second-wave feminist fed-up-ed-ness.

But what precedes that moment is anguish. In that climactic scene, Rachel thinks this about her husband who's sitting across the table from her:

"I still love you. ... I still find you interesting, ... But someday I won't anymore. And in the meantime, I'm getting out. I am no beauty, ... and I am terrified of being alone, ... but I would rather die than sit here and pretend it's okay, I would rather die than sit here figuring out how to get you to love me again. ... I can't stand sitting here with all this rage turning to hurt and then to tears."

Like her idol, Dorothy Parker , Ephron knew that the greatest comedy arises out of finding ironic distance and, therefore, control over the things that make us wince, cry, despair. Ephron left us not only that key lime pie recipe, but also her recipe for coping.

And, speaking of coping, for many of us readers, coping with late winter blahs means reaching for a comic novel; not only classics like Heartburn , but also the work of new writers, such as Jenny Jackson. Her debut novel, Pineapple Street , is being likened to the work of another late, great, essentially comic writer, Laurie Colwin , because both focus on the foibles of old money families in New York City.

That comparison is a bit overblown, but Jackson's Pineapple Street stands on its own as a smart comedy of manners. This is an ensemble novel about members of the wealthy Stockton family that owns swaths of Brooklyn Heights and beyond. The most engaging plotline involves a daughter-in-law named Sasha, who hails from a "merely" middle-class background, and struggles to fit in. When her in-laws come to dinner, for instance, their indifference to her food makes her feel "like the lady at the Costco free sample table, trying to sell warm cubes of processed cheese."

Even the most insular characters in Pineapple Street , however, are aware of their privilege. Humor, being topical and dependent on sharp observation of behavior and detail, needs to keep in step with changing times, as Jackson does here. But the shock of social recognition — the moment when a good writer transforms an everyday detail about cheese cubes into an observation about the casual cruelties of class hierarchy — remains as jolting as getting or throwing a pie in the face. Here's to being the thrower!

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Pineapple Street: A Novel Kindle Edition

• Print length 316 pages
• Language English
• Sticky notes On Kindle Scribe
• Publisher Viking
• Publication date March 7, 2023
• File size 4107 KB
• Page Flip Enabled
• Word Wise Enabled
• Enhanced typesetting Enabled
• See all details

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Editorial Reviews

Amazon.com review, about the author, excerpt. © reprinted by permission. all rights reserved., product details.

• ASIN ‏ : ‎ B0B3HHF1HL
• Publisher ‏ : ‎ Viking (March 7, 2023)
• Publication date ‏ : ‎ March 7, 2023
• Language ‏ : ‎ English
• File size ‏ : ‎ 4107 KB
• Text-to-Speech ‏ : ‎ Enabled
• Screen Reader ‏ : ‎ Supported
• Enhanced typesetting ‏ : ‎ Enabled
• X-Ray ‏ : ‎ Not Enabled
• Word Wise ‏ : ‎ Enabled
• Sticky notes ‏ : ‎ On Kindle Scribe
• Print length ‏ : ‎ 316 pages
• Page numbers source ISBN ‏ : ‎ 0735244413
• #1,176 in Literary Sagas
• #1,682 in Women's Sagas
• #3,952 in Romance Literary Fiction

About the author

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.

Customer reviews

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Customers say

Customers find the writing quality very well written and enjoyable. They also describe the tone as funny in places and witty in others. Opinions are mixed on the characters, with some finding them well-developed and others saying they didn't really develop. Readers also have mixed feelings about the plot, with others finding it unique and interesting, while others say it's predictable and slow.

AI-generated from the text of customer reviews

Customers find the book enjoyable, interesting, and a great escape. They also say the plot is not drama-filled.

"This was a fun and easy read with good life lessons of family, meaning, and money, a nice complete story" Read more

"It’s a good book , but not one that is super engaging. It was one that was entertaining enough to keep reading and one that I could put down." Read more

"...Couldn’t quite figure out how it would wrap, but it was satisfying enough ." Read more

"I could not put the book down!! It was not boring . The characters in the story were excellent. This book was well written...." Read more

Customers find the writing quality of the book very well written and insightful. They also say the characterizations are excellent.

"...The characters in the story were excellent. This book was well written . It truly does make a family. It was a very enjoyable read...." Read more

" Light and enjoyable read , but the characters did not really develop. My favorite characters were Tilda and Sasha because they were true to themselves." Read more

"It is a very light read . I didn’t think it offered much drama or suspense." Read more

Customers have mixed opinions about the plot. Some find the characters wonderful, compelling, and entertaining. They also describe the family drama as thought-provoking, and the ending as pleasantly upbeat. However, others feel the plot is lacking and repetitive.

"This was a fun and easy read with good life lessons of family , meaning, and money, a nice complete story" Read more

"It’s a good book, but not one that is super engaging . It was one that was entertaining enough to keep reading and one that I could put down." Read more

" Interesting enough story of a family with means and misunderstandings aplenty. Likable characters. Some surprises...." Read more

"...However, it was kind of like a more boring version of Jerry Seinfeld - relatively shallow people moving along without any sort of plot...." Read more

Customers have mixed opinions about the characters in the book. Some find them well-developed, while others say they were never fully developed.

"... Likable characters . Some surprises. Couldn’t quite figure out how it would wrap, but it was satisfying enough." Read more

"Light and enjoyable read, but the characters did not really develop . My favorite characters were Tilda and Sasha because they were true to themselves." Read more

"I could not put the book down!! It was not boring. The characters in the story were excellent . This book was well written...." Read more

"...The plot is basic, but it’s character-driven , and the novel’s themes of social problems, elitism and nepotism are very timely...." Read more

Customers are mixed about the tone. Some find the writing catchy, funny, witty, and charming. They also say it brings smiles and feelings. However, others find the book patronizing, insightful, and lacking in insight. They mention that the book has laughable grammatical errors and liberal misguidance.

"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..." Read more

"...Also I never thought it was funny , I felt sorry for almost all the characters." Read more

" Brimming full of dark humor , “Pineapple Street” is a social satire of New York’s 1 Percent..." Read more

"Expected more based on the reviews in the NYT. Not as clever or entertaining as I had hoped when I paid full price for this book a few months ago...." Read more

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