“I live in Brooklyn. By choice.” – begins Jenny Jackson’s debut novel, Pineapple Street, with this Truman Capote quote, setting the perfect tone for what unfolds as a sharply observed tale of money, class, and familial bonds in Brooklyn Heights.
In Pineapple Street, Jackson delivers a wickedly funny yet emotionally nuanced portrait of the Stockton family—old-money Brooklyn Heights aristocracy navigating the complexities of inheritance, marriage, and identity in a rapidly changing New York. The novel skillfully balances social satire with genuine heart, taking readers into a world where $40 million trust funds exist alongside existential crises about purpose and belonging.
The Fruit Streets’ Finest
The story revolves around three women at different stages of their relationships with the Stockton fortune:
Darley: The eldest Stockton daughter who gave up her trust fund by choosing not to have her husband sign a prenup
Sasha: A “middle-class” Rhode Islander who married into the family and finds herself labeled “the Gold Digger” by her sisters-in-law
Georgiana: The youngest Stockton, grappling with a devastating love affair and questions about her privileged position in society
Jackson alternates between these three perspectives, weaving their stories together to create a rich tapestry of family dynamics, class tension, and personal growth. Each woman provides a unique lens through which we view the same family: Darley from inside the fold but financially distanced, Sasha as the newcomer trying to find her place, and Georgiana as the insider questioning everything she once took for granted.
Wealth as Character
What makes Pineapple Street particularly compelling is how Jackson treats wealth itself as a character—one that shapes, limits, and defines everyone it touches. The Stockton fortune isn’t simply money in the bank; it’s generations of accumulated privilege, expectation, and insularity:
“They were a pack of fancy poodles, and she felt like a guinea pig shivering with nerves.”
Jackson expertly captures the subtle ways wealth manifests, from the “tablescape” obsessions of family matriarch Tilda to the casual way they dismiss million-dollar real estate decisions as “rounding errors.” The novel is at its most incisive when examining how money shapes relationships:
“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.”
Pitch-Perfect Dialogue and Social Observation
One of Jackson’s greatest strengths is her ear for dialogue. The Stockton family speaks in a language of coded signals, inside references, and carefully calibrated class markers. Their conversations reveal character while simultaneously moving the plot forward, a difficult balance that Jackson makes look effortless:
“In my day, things were so much simpler,” Georgiana’s mother tutted. “You just went out with your deb ball escort or maybe your brother’s roommate from Princeton.”
“Right, Mom, but people my generation aren’t giant elitist snobs,” Georgiana said and rolled her eyes.
The novel also shines in its anthropological attention to the details of upper-class life. From the tennis matches at “the Casino” (their racket club) to the intricacies of fundraising auctions at private schools, Jackson renders this world with the precision of someone who has both observed it closely and maintained enough distance to see its absurdities.
Emotional Depth Beneath the Satire
While Pineapple Street could have remained a simple satire of the wealthy, Jackson elevates her narrative by giving her characters genuine emotional struggles:
Sasha’s complex relationship with her working-class background and her former boyfriend Mullin
Darley’s crisis when her husband loses his banking job and challenges her identity as both a Stockton and a Kim
Georgiana’s devastating affair with a married colleague and her subsequent awakening to the unequal world outside her bubble
These emotional threads keep the novel from feeling superficial, even as it skewers the more ridiculous aspects of wealth. Each woman grows throughout the story, finding her way to authentic connection despite the barriers money creates.
Critiques: Plotting and Pacing
The novel’s most notable weakness lies in its somewhat uneven pacing. The first half builds the characters and their world beautifully, but the latter half occasionally feels rushed, particularly in resolving major conflicts. The fire that damages the Pineapple Street house near the end feels more like a convenient plot device than an organic development, allowing for a physical transformation that mirrors the emotional changes the characters have undergone.
Additionally, some readers may find Georgiana’s transformation from privileged party girl to passionate philanthropist happens too quickly to be entirely convincing. While her motivations are well-established through her grief over Brady, her shift from guilt to purpose could have benefited from more developmental steps.
A Sense of Place: Brooklyn Heights as Setting
Jackson’s portrayal of Brooklyn Heights deserves special mention. The “fruit streets” neighborhood (named for streets like Pineapple, Orange, and Cranberry) becomes another character in the novel—historic, prestigious, and resistant to change:
“For all their investment in converting old buildings to new high-end condos, they made their home in a section completely barred from significant change by the Landmarks Preservation Commission.”
This setting provides the perfect metaphor for the Stocktons themselves: beautiful, historic, and fighting to preserve a way of life that may no longer be sustainable in a changing world.
Standout Scenes
Several scenes showcase Jackson’s talent for balancing humor with emotional truth:
The moment Sasha discovers her sisters-in-law call her “the Gold Digger” behind her back
Georgiana’s humiliating blue cocktail meltdown at the gender reveal party
Darley’s children becoming obsessed with death, leading to a memorable pigeon incident
The family dinner where Tilda asks Sasha to tell them about “growing up poor”
These set pieces blend comedy with genuine emotional stakes, proving Jackson’s skill at handling tonal shifts.
Final Assessment: A Memorable Debut
Pineapple Street announces Jenny Jackson as a formidable new voice in contemporary fiction. Drawing on her experience as an editor at Knopf, Jackson has crafted a novel that feels both classic in its family drama and thoroughly modern in its examination of class and privilege. The novel rewards readers with:
Razor-sharp dialogue and social observation
Complex, flawed, yet ultimately sympathetic characters
A vivid sense of place and culture
Meaningful explorations of wealth, class, and belonging
Genuine emotional growth alongside satirical humor
The book invites comparisons to Cynthia D’Aprix Sweeney’s The Nest and Meg Wolitzer’s The Interestings in its examination of family dynamics and wealth, while its focus on old money Brooklyn brings to mind Amor Towles’ Rules of Civility transposed to a contemporary setting.
Who Should Read It
Pineapple Street will appeal to:
Readers who enjoy social satire with heart
Fans of family dramas with multiple perspectives
Anyone fascinated by the dynamics of wealth and class
Those who appreciate strong female protagonists navigating complex relationships
New Yorkers and anyone interested in the unique culture of Brooklyn Heights
What makes Jackson’s debut particularly special is how it manages to critique wealth and privilege while still treating its wealthy characters as fully human. It understands that even those who seem to have everything still struggle with universal human concerns: belonging, purpose, and love.
In the end, Pineapple Street is like the neighborhood it portrays—beautiful, complex, layered with history, and full of surprising corners to explore. Jackson has given us a novel that entertains magnificently while quietly asking important questions about what we value and why.
Pineapple Street marks the arrival of a writer with both a keen eye for social observation and a generous heart for human foibles. While this is Jackson’s debut novel, her years as a vice president and executive editor at Knopf have clearly honed her storytelling instincts to a fine edge. Readers will eagerly await what she does next.