“Pineapple Street” is an addictive novel that explores themes of privilege, wealth and love. Written by author Jenny Jackson, the book follows the story of one of New York’s one-percenter families: The Stocktons. Through the perspectives of three women — Darley, Sasha and Georgiana — Jackson dives into modern life in Brooklyn Heights and the ins and outs of one of New York’s richest families.
The story unfolds from three different perspectives: First is Darley Stockton, the eldest daughter of the Stockton family, who trades her large inheritance in exchange for the husband of her dreams and a chance at motherhood. Next is Sasha, a middle-class girl who married into the family and quickly became an outsider, and lastly is Georgiana, the baby of the family, who is still figuring out the person she wants to be. While these three women are at different points in their lives, Jackson does a great job of connecting their experiences and stories to bring the novel together.
An overarching theme of this book is money and the divide it can cause. Sasha, who married Cord, the youngest son of the Stockton family, finds herself never feeling like she truly fits into the ultra-rich family’s world. When Sasha and Cord move into the family’s grand Brooklyn Heights home after their marriage, tension arises between the three women because the house was meant for a Stockton daughter. This tension leads Darley and Georgiana to make sure Sasha never feels like she belongs. While she is technically a part of the family, Sasha is constantly treated like a guest — or worse, like an intruder.
Darley, who is deemed to be the heir to the empire,” has grown up in a world of immense privilege. Her life has been filled with wealth, tradition and a whirlwind of unspoken rules that come with New York society. Darley is married to Malcolm, whom she truly loves. In a bold move, Darley decides to pick her marriage over financial independence and eventually motherhood over a successful career. Throughout the book, she finds herself making sacrifices for the benefit of others, and she constantly struggles with whether she has made the right choices.
While Sasha and Darley have their lives somewhat together, Georgiana is the exact opposite. Carefree and impulsive, she finds herself in quite a predicament when she falls in love with her married boss, Brady. This causes her to question her moral compass and think deeply about the ethics of her rash decisions. As the book goes on, it becomes clear that Georgiana doesn’t fully realize the privilege she has grown up with and continues to have. Living rent-free in one of her family’s mansions, she lives a well-cushioned life that doesn’t have much accountability. But when tragedy eventually strikes, she is forced to confront her choices and finally deal with the harsh realities of life. As the story progresses, each woman confronts how her identity has been shaped—or erased—by marriage, family and societal expectations.
Jenny Jackson’s writing is sharp and observant, yet also has a lighter touch. Using humor and irony, Jackson explores a multitude of serious topics. While the novel revolves around New York’s richest, Jackson portrays all of the characters in a way that makes them feel real and, more importantly, relatable. If you’re looking for a lighter novel that will keep your attention, “Pineapple Street” is worth the read!
