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.

Sasha is one of the novel’s three protagonists, sharing the role with her sisters-in-law, Darley and Georgiana. Sasha has carefully chosen Cord as a husband who loves but does not need her, and she is happily married to him, even as his parents and sisters mystify her. How to comprehend a family that offers her an enormous house to live in, free of charge, but still refuses to make room for her in any meaningful way?

Back in Rhode Island, her own hardworking family is so porous that it has essentially absorbed her ex-boyfriend, keeping his favorite foods in their pantry and setting out a stocking for him at Christmas. (They were “a restaurant booth. You could always scoot in and make space for one more. Cord’s family was a table with chairs and those chairs were bolted to the floor.”) It’s a mystery that intrigues and even amuses her, at least until she overhears her sisters-in-law referring to her as a gold digger — an insult arising from an unfortunate misunderstanding about a prenup. What makes Sasha different from her fellow Stocktons is so apparent that her in-laws’ friends mistake her for a server at their parties, even when she attempts to introduce herself. “Oh, I’m Sasha,” she says, as a guest tries to hand her an empty glass. “Thank you, Sasha,” the guest replies, cheerfully.

It’s no wonder, then, that Sasha is in the dark about a few key current events in the family. Darley is married to Malcolm, a Korean American consultant with a passion for all things aviation. Darley’s own decision not to insist on a prenup reflects the fact that her husband is on the cusp of a great career, and the agreement itself “felt like arranging their eventual divorce.”

Besides, Darley takes less of an entitled view of her wealth: “She didn’t feel the money belonged to her anyway. It belonged to her grandparents and her great-grandparents. She had done nothing but act as a drain — private school and vacations and clothing and death by the thousand cuts that was raising a child in the most expensive city in America.”

Practically speaking, forgoing the same prenup her sister-in-law, Sasha, will eventually confront means passing her trust fund down to her two children. Metaphorically speaking, the decision is on par with a life-altering gamble in which she has “locked herself out of her own inheritance and bet all her chips on love.” Not such a concern when her husband’s career is thriving, but then Malcolm is collaterally damaged by the careless actions of a co-worker, and it starts to look like a bad bet. Naturally, she tells not a single Stockton about this reversal of fortune.

Georgiana is keeping a few secrets of her own. The youngest Stockton carefully withholds news of an ill-advised affair with a colleague when she’s hobnobbing at family gatherings, including regular tennis matches with her mother. This culminates in a uniquely 1 percent crisis; when Georgiana, reeling from a traumatic event and too many costume parties, takes the major step of finally opening the statements for her trust accounts — “one from GeeGee and DeeDee and one from Pip and Pop” — she discovers that her personal fortune runs to eight figures. What is to be done with such alarming information? What is privilege supposed to be for, if personal happiness seems so utterly beside the point? For that matter, what is the point of a family — even an insular and overly involved family — if one doesn’t turn to them when it matters?

The author — a respected editor at Alfred A. Knopf — has an obvious familiarity with the “fruit streets” of Brooklyn Heights, and the families who inhabit them. The enmeshment of those families has a haunting counterpart in the area’s former occupation by the Jehovah’s Witnesses, whose tunnels connected (and perhaps still connect) many of the properties the church once owned. Those tunnels might have made sense when everyone belonged to the same organization, but what can they mean for a modern Brooklyn neighborhood? “What were you supposed to do when there was a whole underground lair full of laundry rooms and storage cages connecting your apartment building to a stranger’s?” What indeed?

“Pineapple Street” has more in common with a backward-gazing Gilded Age novel like John P. Marquand’s 1937 blockbuster “ The Late George Apley ” than with, say, a Gilded Age novel written during the actual Gilded Age, but Marquand’s long-ago readers probably weren’t conflicted about the subject matter; one can’t quite imagine a 1937 book group debating the justification for reading about such wealthy and insular people, let alone Marquand wrestling with whether it was appropriate to be writing about them! Today, doing either feels almost defiant.

And while Jackson’s characters are admirably complex and not un-self-aware, and while they do ruminate on privilege and what it provides — Darley’s version invokes the “respectable” pursuit of high-priced academia, while Sasha’s involves her “infamous” cousins who “avoided mile-long rap sheets” thanks to their dad, the local chief of police — the concept of entitlement never quite leaves the novel’s background. What remains resolutely in the foreground? Those “tablescapes,” lost items of jewelry, expensive private schools, trust funds and, of course, the pesky prenups that help drive the plot, just as they drove the plots of Austen, Dickens, Trollope … and even that guy who wrote about the very rich a century ago.

Take these things as they are or don’t take them at all; the novel and its author offer no apologies. And if you prefer not to read about absurdly wealthy people and their very human problems? Well, you’re in luck, because our current “shelfscape” is rich in novels about people who are not absurdly wealthy, and their very human problems. Because, let me tell you about the very poor: They are not so different from you and me, either.

Jean Hanff Korelitz’s latest novel is “The Latecomer.”

PINEAPPLE STREET | By Jenny Jackson | 320 pp. | Pamela Dorman Books | $28

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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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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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DEMON COPPERHEAD

by Barbara Kingsolver ‧ RELEASE DATE: Oct. 18, 2022

An angry, powerful book seething with love and outrage for a community too often stereotyped or ignored.

Inspired by David Copperfield , Kingsolver crafts a 21st-century coming-of-age story set in America’s hard-pressed rural South.

It’s not necessary to have read Dickens’ famous novel to appreciate Kingsolver’s absorbing tale, but those who have will savor the tough-minded changes she rings on his Victorian sentimentality while affirming his stinging critique of a heartless society. Our soon-to-be orphaned narrator’s mother is a substance-abusing teenage single mom who checks out via OD on his 11th birthday, and Demon’s cynical, wised-up voice is light-years removed from David Copperfield’s earnest tone. Yet readers also see the yearning for love and wells of compassion hidden beneath his self-protective exterior. Like pretty much everyone else in Lee County, Virginia, hollowed out economically by the coal and tobacco industries, he sees himself as someone with no prospects and little worth. One of Kingsolver’s major themes, hit a little too insistently, is the contempt felt by participants in the modern capitalist economy for those rooted in older ways of life. More nuanced and emotionally engaging is Demon’s fierce attachment to his home ground, a place where he is known and supported, tested to the breaking point as the opiate epidemic engulfs it. Kingsolver’s ferocious indictment of the pharmaceutical industry, angrily stated by a local girl who has become a nurse, is in the best Dickensian tradition, and Demon gives a harrowing account of his descent into addiction with his beloved Dori (as naïve as Dickens’ Dora in her own screwed-up way). Does knowledge offer a way out of this sinkhole? A committed teacher tries to enlighten Demon’s seventh grade class about how the resource-rich countryside was pillaged and abandoned, but Kingsolver doesn’t air-brush his students’ dismissal of this history or the prejudice encountered by this African American outsider and his White wife. She is an art teacher who guides Demon toward self-expression, just as his friend Tommy provokes his dawning understanding of how their world has been shaped by outside forces and what he might be able to do about it.

Pub Date: Oct. 18, 2022

ISBN: 978-0-06-325-1922

Page Count: 560

Publisher: Harper/HarperCollins

Review Posted Online: July 13, 2022

Kirkus Reviews Issue: Aug. 1, 2022

LITERARY FICTION | GENERAL FICTION

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Pineapple Street by Jenny Jackson review – smart debut about wealthy New Yorkers

Minutely observed and packed with one-liners, this tale of the 1% insists on giving the super-rich a chance

S ince F Scott Fitzgerald first described the view from a West Egg mansion, the lives of the American 1% have been of keen interest to the rest of us; whether we love them, love to hate them or want to know where they buy their shoes. And these days, with Succession and The White Lotus streaming to record audiences, the power struggles, moral dilemmas, interior designers and dirty secrets of the obscenely wealthy are big business.

This, then, is the train to which Jenny Jackson’s entertaining debut novel Pineapple Street hitches its wagon. Her focus is on the Stockton family of Brooklyn, high net worth Wasp buccaneers of New York real estate. They consist of air-headed matriarch Tilda, obsessed with tennis and tablescapes; her husband, the amiable Chip, who quietly manages the empire; daughters Darley and Georgiana; and son Cord. Pampered, naive Georgiana works for a charity and Darley and Cord have both “married out”. Darley has renounced her trust fund because she refused a prenuptial agreement to wed tender-hearted nerdy Malcolm, aviation whiz and a second-generation immigrant of colour, while Cord, who works alongside his father, has just married Sasha, a graphic designer from a rough and ready blue-collar Rhode Island family.

Sasha is our witness to the lives of the wealthy, parachuted into the family townhouse on the titular Pineapple Street when Tilda and Chip decide to downsize to a mere penthouse. Sasha’s sisters-in-law call her “the gold-digger” behind her back, because she was shocked by the idea of signing a prenup. The ripples surrounding the move soon widen, taking us from Sasha’s profound sense of not belonging in Pineapple Street to Georgiana’s unease at being a trust fund baby working to combat poverty in the developing world. Darley is trying to manage motherhood alongside a feeling of having been ousted from the family nest and, when Malcolm is betrayed by Wasp colleagues in the workplace, the prospect of not being rich at all. And when actual tragedy intervenes, the question is whether lives cushioned – or numbed – by privilege can survive it any better than the rest of us.

Smart and clever, minutely observed and packed with one-liners, Pineapple Street is a more complicated read than it looks. But while Jackson regularly checks her characters’ privilege, The Bonfire of the Vanities t his is decidedly not. The author insists that we give the super-rich a chance, and this approach risks softening the narrative’s centre. The White Lotus and Succession are largely popular because they are packed with satisfying villains; Pineapple Street has none. From the cars they drive to the delis they favour, the granular detail of the Stocktons’ lives is happily catalogued with what Edith Wharton , queen-chronicler of New York snobbisms, called “the minute statistical information of a gazetteer”. It can sometimes feel as if we are drowning, like Sasha, in possessions and signifiers of affluence.

There’s a queasy line to be trod, too, when arbitrating between good and bad wealth: real estate good, arms dealers – who crop up late in the novel – bad? And in a climate emergency, good guy Malcolm’s career in aviation can hardly be said to be saintly. Jackson sticks her neck out by keeping the focus largely on spoilt Georgiana while leaving the more decent Sasha and her regular family on the back burner; this pays off, giving the narrative redemptive possibilities and some much-needed edge. Tilda’s superficiality teeters on the verge of one-dimensionality, but her relationship with her daughter, conducted entirely on the tennis court – “competition was their love-language” – is surprisingly poignant in its limitations. And though we have to wait a little too long for Sasha to have her say, when she does, it’s blistering.

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‘Pineapple Street’ gets laughs from tensions among the 1 percent

Jenny jackson’s debut novel is about siblings and their in-laws in a well-to-do brooklyn family.

There are the rich and there are the very rich, and while the very rich exhibit varied demographic characteristics, the family at the center of Jenny Jackson’s sparkling debut novel, “ Pineapple Street ,” is of a highly specific sort: the pedigreed, never-touch-the-trust-fund-principal, tennis-playing, old-money-Brooklyn WASP.

This is not your bubbie’s Brooklyn, not your hipster Brooklyn, not your hour-long-bus-ride-from-JFK-and-crash-on-your-third-cousin’s-sofa Brooklyn. The Stockton family — large-scale real estate investors — live in the historically preserved, quaint, leafy “fruit streets” section of Brooklyn Heights: “Three little blocks of Pineapple, Orange and Cranberry streets situated on the bluff over the waterfront.”

Tilda and Chip have owned their beloved limestone for some 40 years, and it plays such a central role in this novel that it’s a character unto itself, with its velvet window dressings, overstuffed closets and vaguely Dickensian furnishings, including a noisy grandfather clock and a possibly bug-infested antique sofa.

The couple decide to downsize but don’t want to sell their home. So they invite their son, Cord, and his wife, Sasha, to move into the house, the inciting incident of this comedy of the 1 percent.

The young couple may live rent-free, but the arrangement comes with an emotional cost, at least for Sasha, who has little say when it comes to culling any of the items in the overstuffed house. She can’t so much as reconfigure the master bedroom closet without her mother-in-law pushing back, opining on the best way to store “off-season footwear, hats, anything with a brim that you don’t want crushed.” Sasha and Cord even sleep on his parents’ four-poster bed, where “it was extremely hard for Sasha to achieve orgasm while the mahogany headboard that probably belonged to a congressman or secretary of transportation banged against the wall.”

Tilda’s not the only one overly attached to the place — the two other Stockton children, Darley and Georgina, grew up there, and their rooms remain full of old textbooks, photo albums, tennis trophies and school projects, including “an ashtray Darley made in sixth grade that looked like a malformed mushroom.”

The two sisters have nicknamed Sasha, who comes from a middle-class family and who they believe refused to sign a prenuptial agreement, the Gold Digger; the GD, for short.

Darley is meanwhile wrestling with her own family problems. Her Korean American husband, Malcolm, has just lost his job in the Aviation Group at Deutsche Bank. Again with the pre-nups: Darley did not ask Malcolm to sign one, so she has been cut out of her inheritance, which will now skip a generation and go directly to their children. Now that Malcolm is unemployed, and Darley has given up her job at Goldman Sachs to stay home with the children, they are moving toward financial crisis.

Georgiana is the most complicated of the bunch. At 26, she is a well-rendered, often hilariously and disturbingly oblivious millennial who says 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!” Georgiana’s world is so insular that, even though she works for a nonprofit focused on health care in the developing world, she does not know that the United Arab Emirates is a country.

A traumatic event involving her messy love life prompts Georgiana to try to divest herself of her fortune. “It was the money that made her so horrible,” she thinks. “It had made her coddled and spoiled and ruined.” But giving away all of her $37 million will be more complicated than she imagined.

That the book is smart and sharply observed, peppered with small gems, should come as no surprise: Jackson is a vice president and executive editor at Knopf and has worked with a long roster of authorial luminaries.

As the story unfolds, with the Stocktons throwing dinner parties, attending glamorous fundraisers and playing many games of tennis, the longtime housekeeper, Berta, cooks, mops and clears tables in the background. As for Berta, we never learn much about her or what she might be making of this family’s exploits. Jackson hasn’t come here to excoriate the 1 percent, yet I found myself wondering how this novel might look through Berta’s lens. Fans of well-observed foibles will have a ball; class warriors might look elsewhere.

Susan Coll’s most recent novel is “ Bookish People .”

Pineapple Street

By Jenny Jackson

Pamela Dorman Books/Viking. 304 pp. $28

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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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Submitting a book for review, write the editor, you are here:, pineapple street.

PINEAPPLE STREET, a smart first novel from publishing executive Jenny Jackson, takes readers into the exclusive world of the one-percent through the lives of one wealthy family living in Brooklyn Heights.

The Stocktons are a living example of generational wealth in America today. Tilda and Chip raised their family in a gilded limestone on Pineapple Street, one of the many “fruit streets” in their Brooklyn neighborhood. Eldest daughter Darley is married to a banker named Malcolm. When they wed, she declined her trust fund (thereby foregoing the standard prenup that each Stockton spouse is expected to sign) in favor of letting her husband be the breadwinner for their family of four.

"PINEAPPLE STREET is an engaging and absorbing read, with a supremely satisfying conclusion, perfect for book groups or to pass along to a good friend."

Darley’s brother, Cord, works for their father’s real estate investment firm. His wife, Sasha, is the most unlike the rest of the family in more ways than one. She was raised solidly middle class in a seaport town in Rhode Island and has never felt fully accepted into Cord’s family, especially among his sisters. She and Malcolm have a tenuous bond, being the two outsiders, and silently mouth “NMF” (“not my family”) to each other when one of the Stocktons makes a clueless comment about trust funds or flying private. Georgiana is the youngest of the Stockton brood at 26. She has never really thought about their enormous wealth until she suffers a great loss.

The Stockton children never had to worry about money or their financial futures. But when Malcolm is fired from his prestigious banking job --- a secret that Darley keeps from her family --- she starts questioning her decision to turn down her trust fund when they married: “She thought about her own prenup for the millionth time. Maybe she had made a stupid mistake when she gave up her trust, sure. But her biggest mistake had been giving money so much power over her life. By keeping Malcolm’s secret she was buying into the idea that her world was a club only available to those with a seven-figure income.”

Cord and Sasha have moved into the family’s home on Pineapple Street when Tilda and Chip decided to “downsize” to a smaller yet stately apartment on nearby Orange Street. As grateful as Sasha is to her in-laws, the palatial mansion feels a bit staid and outdated for her tastes. She tries to make the place a home for them, but her mother-in-law dissuades her whenever she attempts any alterations: “The more Sasha thought about it, the angrier she felt. She was stuck in a lose-lose situation, a member of a family in which she had no voice, she had no vote, where doors were closed and envelopes remained sealed and money was a string that tied them all together and kept them bound and gagged.” Sasha feels even more distanced from the Stocktons when she overhears Darley and Georgiana call her a “gold digger” at a family wedding. She’s had enough.

Georgiana divides her twenty-something time between her job at a local non-profit and her family’s private tennis club. When she begins an ill-advised affair with a married coworker, she begins to question not only her own morals but also her place in the world. An impromptu meeting with school friend Curtis McCoy, a wealthy nepo baby who wants to rid himself of his family’s fortune (gained through military manufacturing), rattles Georgiana to her core. He informs her, “Income inequality is the most shameful issue of our time. I’m worried that my kids will look back and see a country that completely abandoned morality, that let people die of hunger while the wealthy took tax breaks.” Georgiana has an epiphany: “It was the money that made her so horrible. It had made her coddled and spoiled and ruined, and she had no idea what to do about it.”

Jenny Jackson’s deft debut takes on the topic of generational wealth with a keen Austenian eye, but she refrains from harshly judging her characters. She leaves it up to her readers to make up their own minds. As an inhabitant of Brooklyn Heights herself, Jackson lives among families like the Stocktons, making her a perceptive observer of their kind. PINEAPPLE STREET is an engaging and absorbing read, with a supremely satisfying conclusion, perfect for book groups or to pass along to a good friend.

Reviewed by Bronwyn Miller on April 6, 2023

Pineapple Street by Jenny Jackson

• Publication Date: March 12, 2024
• Genres: Fiction , Women's Fiction
• Paperback: 320 pages
• Publisher: Penguin Books
• ISBN-10: 0593490711
• ISBN-13: 9780593490716

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Look Inside | Reading Guide

Reading Guide

Pineapple Street

A GMA Book Club Pick (A Novel)

By Jenny Jackson

By jenny jackson read by marin ireland, category: women's fiction | literary fiction, category: women's fiction | literary fiction | audiobooks.

Mar 12, 2024 | ISBN 9780593490716 | 5-5/16 x 8 --> | ISBN 9780593490716 --> Buy

Mar 28, 2023 | ISBN 9780593676714 | 6-1/8 x 9-1/4 --> | ISBN 9780593676714 --> Buy

Mar 07, 2023 | ISBN 9780593490693 | 6 x 9 --> | ISBN 9780593490693 --> Buy

Mar 07, 2023 | ISBN 9780593490709 | ISBN 9780593490709 --> Buy

Mar 07, 2023 | 513 Minutes | ISBN 9780593670620 --> Buy

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Mar 12, 2024 | ISBN 9780593490716

Mar 28, 2023 | ISBN 9780593676714

Mar 07, 2023 | ISBN 9780593490693

Mar 07, 2023 | ISBN 9780593490709

Mar 07, 2023 | ISBN 9780593670620

513 Minutes

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About Pineapple Street

A New York Times bestseller | A Good Morning America Book Club Pick Chosen as a best book of the year by The New York Tim es | 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.

A Good Morning America Book Club Pick “A vibrant and hilarious debut… Pineapple Street is riveting, timely, hugely entertaining and brimming with truth.” —Cynthia D’Aprix Sweeney, New York Times bestselling author of The Nest “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.

Listen to a sample from Pineapple Street

About 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, she lives in Brooklyn Heights with her family. Pineapple Street is her first novel.

Product Details

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Praise for Pineapple Street : “A delicious new Gilded Age family drama—almost a satire—set in the leafy enclaves of Brooklyn Heights….A lighthearted book that captures a slice of New York society, a guilty pleasure that also feels like a sociological text, punctuated with very particular references to restaurants, preschools, nightclubs, and other pillars of urban life in 2023.” — Vogue “Those who want to eat the rich may salivate while reading Pineapple Street …This breezy read is the bookish equivalent of an effervescent Netflix dramedy. Expect to be entertained.” – The Wall Street Journal “[An] engaging debut.” – The New Yorker “A witty, easy-to-devour story of wealth and love’s never-ending war in the modern age.” — Elle “This witty novel about the haves and have-mores is Succession with a soul.” — TIME “Sparkling….The book is smart and sharply observed, peppered with small gems.” — The Washington Post “A smart comedy of manners… 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!” —Maureen Corrigan, Fresh Air “Love is at the heart of this sparkling debut novel by Jenny Jackson, which excavates old money and contemporary problems with satiric flair.” — Southern Living “This delicious family saga provides a voyeuristic look into the lives of an ultra-wealthy Brooklyn Heights clan. Expect doomed romances, real estate dealings and lots of tennis.” — New York Post “This novel…is laugh-out-loud good….Love and money have always mixed like oil and water (not well), but Jackson finds new humor and warmth in her particularly witty debut.” — Harper’s Bazaar “A novel about inheritance and the cultural inanities of the American WASP, set in a maximalist mansion? Don’t mind if I do. Pineapple Street is more than a field report on the WASPs and their shabby-sweater super-wealth, of course—it’s about class difference and the taxations of love.” —Bustle “Let us now praise purely escapist novels that fizz and pop….Jackson…has a golden ear for the gilded social stratas of New York money, and all the cocktail benefits and secret codes that come with them.” — Entertainment Weekly “Every single character bursts off the page. Seriously. Pineapple Street is just the right witty, entertaining story to usher in spring.” — Real Simple “A charming, funny, and keenly observed story about New York City’s one percent—and what it means to find yourself among them, whether by birth or marriage.” — Town and Country “A wealthy Brooklyn Heights family has drama to spare — not to mention plenty of trust funds — in this modern take on a Gilded Age novel.” — The New York Post “ Pineapple Street encapsulates the oftentimes ridiculous nature of the ultra-wealthy. The author seamlessly immerses readers in the lives of the Stocktons…[who] must ask themselves the uncomfortable question: Is it possible to be “good” with this much money?” —Shondaland “There is a particular pleasure to reading about the languid rich: people with names like Poppy and Georgiana, who quake under the pressure of owning too many properties and whose biggest problems involve accidentally leaving their Cartier bracelet in the BMW of a friend who’s about to leave for Southampton. In her debut novel Jenny Jackson delivers a very funny domestic drama of a family drowning in their own excess and over-education. You will heartily enjoy judging them.” — Glamour “Smart and clever, minutely observed and packed with one-liners, Pineapple Street is a more complicated read than it looks… surprisingly poignant.” — The Guardian “ Pineapple Street is a great send-up of rich people, but it’s more than that. Jackson’s characters are privileged, but not one-dimensional buffoons (with the possible exception of matriarch Tilda, who gives off real Mrs. Bennett vibes). Rather, they are complicated, funny, thoughtful, and likable, and it’s that humanity that had me listening to the audiobook deep into the night, devouring all the delicious details, plot twists, and coming-of-age revelations.” — Mother Jones “This is a literary version of The Real Housewives . Filled with fun, sometimes sloppy, characters with an enchanting and enthralling plot. This is the perfect book to shake off the winter snow with. Hot, hot hot.” —Debutiful “Packed with the pleasures of New York’s one-percent, wealth mixes with family and love in this witty debut.” —SheReads “Filled with humor, love, the ups and downs of marriage, and tennis whites, this family’s story is both endearing and exasperating. Readers will enjoy the author’s exploration of both the perks and downsides of generational wealth.” —Booklist “A family drama dripping in gossip, sabotage, and old-school New York luxury.” — Popsugar “Jenny Jackson’s deft debut takes on the topic of generational wealth with a keen Austenian eye…an engaging and absorbing read, with a supremely satisfying conclusion, perfect for book groups or to pass along to a good friend.” —Bookreporter.com “Jackson has a deft hand….Rich-people jokes, cultural acuity, and entertaining banter keep this novel moving at a sprightly pace….A remarkably enjoyable visit with the annoying one percent, as close to crazy rich WASPs as WASPs can get.” — Kirkus “Brooklyn socialites, trust funds, and family secrets are at the center of this un-put-downable comedy… [ Pineapple Street ] grabs your attention and keeps it.” —TheSkimm “Witty, escapist and full of heart, with a cast of loveable flawed characters, Pineapple Street is a beautifully observed novel about the complexities of family dynamics, while also asking the age-old question: can money really buy you happiness?” — SheerLuxe “[A] brilliant debut. . . . It’s both sharply drawn and compassionate.” — BBC “Pineapple Street is that rarest of gifts—a novel you don’t want to put down for anything. Transporting and laugh-out-loud funny, this intergenerational story is a perfect tale for our times.” —J. Courtney Sullivan, New York Times bestselling author of Friends and Strangers “In this vibrant and hilarious debut, Jenny Jackson has taken a familiar tale—siblings, family money, competing interests—and given it fresh life. What binds the book together so wonderfully is Jackson’s keen understanding of the beauty and difficulty of belonging, of how our desires can clash with our inherited narrative and what happens to the people we love when we need to rewrite the story. Pineapple Street is riveting, timely, hugely entertaining and brimming with truth.”  —Cynthia D’Aprix Sweeney, New York Times bestselling author of The Nest and Good Company “Jenny Jackson delivers SUCH a delicious treat with her debut novel, Pineapple Street . It delights across the board — character (the wealthy, quirky Stockton family), setting (an insider’s look at Brooklyn) and plot (a searingly honest exploration of class and privilege.)  With shifting points of view and smart, laugh-out-loud observations on every single page, Pineapple Street is an instant classic.” —Elin Hilderbrand, #1 New York Times bestselling author of The Hotel Nantucket “Set in the windy, sun-dappled streets of Brooklyn Heights, Pineapple Street is a portrait of a NY family strait-jacketed by their own wealth that is at once searing, hilarious and poignant.” —Miranda Cowley Heller, #1 New York Times bestselling author of The Paper Palace “I loved Pineapple Street . The characters are complex and engaging and their stories bring a particular slice of New York magically alive. So wise, emotionally honest, and such fun!” — Helen Fielding, #1 bestselling author of Bridget Jones’s Diary   “Full of witty and caustic observations about a privileged class of New Yorkers, Pineapple Street is a sharp and juicy satire.” —Nita Prose, #1 New York Times bestselling author of The Maid  “I was entranced by Pineapple Street . Smart and complex, rich and gorgeous, this novel drew me in from page one. Both an escape into the lives of the fabulously wealthy and a bittersweet examination of family and heartbreak, Jenny Jackson’s debut left me eagerly awaiting whatever magic she conjures next.” — Amanda Eyre Ward, New York Times bestselling author of The Lifeguards “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.” —Chris Bohjalian, #1 New York Times bestselling author of The Flight Attendant and The Lioness   “Nothing beats a story told this well…. I could not stop laughing at this hilarious insider’s view of Brooklyn Heights WASPs. Truly the smartest and most deliciously fun novel I’ve read in ages.” — Kevin Kwan, New York Times bestselling author of Crazy Rich Asians “ Pineapple Street might be the Edith Wharton novel for our times…Wise, funny, tender, and utterly relatable.” —Susie Yang, New York Times bestselling author of White Ivy “A delight to read from start to finish, Jenny Jackson’s Pineapple Street is a cancel-all-plans kind of book. Utterly addicting, big-hearted and affecting, and full of delicious details, Jackson lets us into an outrageous world of generational wealth and privilege through the eyes of three fallible yet lovable women navigating the complexities of life on the inside. If I could have put this novel on a drip straight into my veins, I would have!” —Ashley Audrain, New York Times bestselling author of The Push “If you’re in search of the fiction trifecta – a captivating story that’s masterfully constructed, vividly peopled, and crisply written – look no further. Jenny Jackson’s “Pineapple Street,” is pure reading pleasure, hilarious, big-hearted, and full of emotional truths. It’s the kind of novel you hope will never end.” — Adrienne Brodeur, New York Times bestselling author of Wild Game “Jenny Jackson has written a lovely, absorbing, acutely observed novel about class, money and love. These are the themes of Henry James and Jane Austen, but they are observed with a fresh eye and a contemporary voice. Who wouldn’t want to read Pineapple Street ?” — Nick Hornby, New York Times bestselling author of Just Like You “I devoured Pineapple Street . Jackson’s writing brims with wit and warmth. Her characters are deliciously flawed and, at the same time, loveable and compelling. Her observations about family, money, class, and love are spot on….[A] messy, hilarious and ultimately relatable family story.” —Cristina Alger, New York Times bestselling author of Girls Like Us “I sucked it down like a milkshake… My favorite part of the novel was the heart. All the characters mess up, but make amends. They TRY. And they keep trying.” —Helen Ellis, author of Bring Your Baggage and Don’t Pack Light

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Jenny Jackson’s 'Pineapple Street' explores the changing landscape of New York’s mega-rich

Much of the buzz around Jenny Jackson’s debut novel, “Pineapple Street,” relates to the author’s impressive credentials as a book editor . In her years at Knopf, Jackson has established herself as a literary hit-maker for such authors as Cormac McCarthy, Gabrielle Zevin, Katherine Heiny and Emily St. John Mandel. This month, she released a book of her own.

“Pineapple Street” is the story of the old-money Stockton family, a carefully guarded clan of one-percenters living among the fruit streets of New York’s Brooklyn Heights neighborhood. Eldest daughter Darley traded her inheritance and her job in finance for motherhood. Sasha married into the family and struggles to fit in. And youngest daughter Georgiana gets entangled in an ill-advised relationship and tries to come to grips with what it means to be a trust-fund baby.

The novel reads like “Crazy Rich WASPs,” with characters uttering lines like, “Oh no, I left my Cartier tennis bracelet in Lena’s BMW, and she’s leaving for her grandmother’s house in Southampton!” The Stockton girls refer to their brother’s wife as “the Gold Digger,” and there’s lots of talk about real estate, private schools, party themes and tablescapes.

But Jackson deftly describes family dynamics — the secrets and passive-aggressive tactics that are so much a part of this social strata. She also explores the changing landscape of the mega-rich, including a younger generation of socialist-minded millennials who feel guilty about their wealth and want to give it away.

At its core, “Pineapple Street” is a contemporary novel of manners and relationships, a peek into how the upper crust lives. It’s a well-written family drama that would make an ideal summer read.

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Book Reviews

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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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 by Jenny Jackson

• Publication Date: March 12, 2024
• Genres: Fiction , Women's Fiction
• Paperback: 320 pages
• Publisher: Penguin Books
• ISBN-10: 0593490711
• ISBN-13: 9780593490716
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Pineapple Street

57 pages • 1 hour read

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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.

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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.

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

• Print length 315 pages
• Language English
• Sticky notes On Kindle Scribe
• Publisher Pamela Dorman Books
• Publication date March 7, 2023
• File size 4438 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 ‏ : ‎ B0B3HPSFJ7
• Publisher ‏ : ‎ Pamela Dorman Books (March 7, 2023)
• Publication date ‏ : ‎ March 7, 2023
• Language ‏ : ‎ English
• File size ‏ : ‎ 4438 KB
• Text-to-Speech ‏ : ‎ Enabled
• Screen Reader ‏ : ‎ Supported
• Enhanced typesetting ‏ : ‎ Enabled
• X-Ray ‏ : ‎ Enabled
• Word Wise ‏ : ‎ Enabled
• Sticky notes ‏ : ‎ On Kindle Scribe
• Print length ‏ : ‎ 315 pages
• Page numbers source ISBN ‏ : ‎ 0735244413
• #16 in Sibling Fiction
• #58 in Women's Literary Fiction
• #128 in Family Life Fiction (Books)

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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.

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