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Book Rec: Pineapple Street by Jenny Jackson

Updated: Jul 6

“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.”


Her debut novel, Pineapple Street is a hilarious look at three women living in the top 1% who I actually grew to empathize with, even though they 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!”


Pineapple Street Book Summary

a beautifully lush rich home behind the title and author

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.


Discussion Guide for Pineapple Street


  1. How would you characterize each sibling’s relationship with the generational wealth they were born into? How do their personalities influence their life experiences and feelings about wealth?

  2. What do you think of the Stockton family? Are they relatable?

  3. The novel’s setting, Brooklyn Heights, serves as a microcosm for the themes of class and identity that permeate the story. In what ways does the neighborhood reflect the broader socioeconomic divisions of America today?

  4. Do you think Brady genuinely loves Georgiana or is he using her for personal gain?

  5. Darley gave up her job and inheritance to get married and become a mother. Was this feminist? When she withholds new of Malcolm’s job loss, is being loyal? Or betraying her husband?



Some content may contain affiliate or referral links. As an Amazon Associate, I also earn from qualifying purchases. When you click on and/or make a purchase through an affiliate link placed on Lifetime Tidbits, I may receive a small commission or other form of compensation at no additional cost to you. Please see my Disclaimers Page for more information. Thank you for reading!

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