Pineapple Street by Jenny Jackson

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Pineapple Street by Jenny Jackson presents the story of three very different women in the Stockton family. Darley, the oldest daughter, made a choice to prioritize motherhood over her job and inheritance, sacrificing more than she bargained for in the process. Sasha, a middle-class girl from New England, marries into the Stockton family and quickly finds herself an outsider in their world of old money and privilege. Georgiana, the youngest of the family, falls for someone she can’t have and must confront who she wants to be in life.

Book review of Pineapple Street

Pineapple Street by Jenny Jackson is a debut novel that tells the story of a wealthy Brooklyn Heights family, the Stocktons, and their newly married son Cord and his wife Sasha. The narrative is told in alternating perspectives of Sasha, Cord’s sisters Georgiana and Darley, giving the reader a chance to explore the various aspects of the family and their unique flaws developed over generations of inherited wealth.

One of the strengths of Pineapple Street is its snarky and character-driven story. Despite being very privileged, the Stockton siblings are not always likable, especially Georgiana and Darley. Jackson masterfully draws out the inherent flaws of each character, creating a cast of complex and deeply flawed characters that are both frustrating and compelling. Even Sasha, the outsider in the family, has a compelling story and unique perspective.

The novel is not without action or plot, but it’s the characters that truly drive the story. Jackson balances the flaws and strengths of each character perfectly, so just when the reader feels repelled, she lures them back in with their kinder sides and potential for growth. Throughout the book, the author weaves in themes of privilege, class, and family dynamics, making it a thought-provoking read.

While the novel’s ending is a bit too neat and tidy, it does not detract from the overall enjoyment of the book. Pineapple Street is a fun and engaging read that is perfect for a vacation or a beach day. It’s a modern-day version of the gilded age, where old-money rich families navigate their lives and relationships. The drama is just right, not too over the top, and meant to be more satirical but still relatable to each of the characters. The humor is on point, and the comical moments will make readers laugh out loud.

Final verdict:

Overall, Pineapple Street is a thoroughly enjoyable read that explores the complexities of family dynamics, wealth, and privilege. It’s a book that will keep readers engaged from start to finish, and it’s definitely worth picking up.

Our Score


  • Engaging Characters: The characters in “Pineapple Street” are complex, multidimensional, and often flawed, making them both realistic and interesting to read about.
  • Witty Writing: The author has a talent for writing witty and sarcastic dialogue, which keeps the tone light and entertaining throughout the book.
  • Satirical Commentary: The novel offers a satirical commentary on the lifestyles and attitudes of the wealthy elite in New York, making it a compelling read for those interested in social commentary.


  • Slow Pacing: Some readers may find the slow pacing of the story to be a drawback, as the novel focuses primarily on character development rather than action.
  • Predictable Plot: The plot of the novel is somewhat predictable, following familiar tropes of family drama and romantic relationships.
  • Lack of Diversity: The novel primarily features wealthy, white characters, which may limit its appeal to readers looking for more diverse representation.
Pineapple StreetPublisher ‏ : ‎ Pamela Dorman Books (March 7, 2023)
Language ‏ : ‎ English
Hardcover ‏ : ‎ 320 pages
ISBN-10 ‏ : ‎ 059349069X
ISBN-13 ‏ : ‎ 978-0593490693
Item Weight ‏ : ‎ 1.15 pounds
Dimensions ‏ : ‎ 6.31 x 1.1 x 9.31 inches

About Article Author

Ethan Davis

Ethan Davis combines his passion for literature with another of his great hobbies: climbing. There is never a mountain high enough for him... nor a book he doesn't want to read, especially if it's a good crime thriller.
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