Sunday Book Review – Pineapple Street by Jenny Jackson

My Sunday Book Review is for Pineapple Street by Jenny Jackson. Thanks to Netgalley for an advanced copy. This is a good escape read about a wealthy family of characters, their dysfunction, and for some – their oblivion about others who don’t come from money.

“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

Darley, the eldest daughter in the closely-tied, carefully-guarded, old money Stockton family, made the classic feminine mistake and gave up her job for her children before she realized she’d sacrificed more of herself than she intended; Sasha married into the Stocktons, and finds herself the outsider looking into the fishbowl, wondering if she will ever understand their ways; and Georgianna, the baby of the family, has fallen in love with someone she can’t (and really shouldn’t) have, and must confront the 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 (and a few appalling ones!), it’s about the peculiar unknowability of someone else’s family, the miles between the haves and have-nots and everything in between, and the insanity of first love—all wrapped in a story that is a sheer delight of a read.

A tale about how the 1% lives and their sometimes, oblivion to how the rest of the world live. It took one of the Stockton children, Cord, to marry out of money to bring awareness to the story by bringing in Sasha to bring attention to reality. The Stocktons come from old money and mother Tilda is both oblivious to those who aren’t as rich as much as she’s oblivious to the what’s really going on with her adult children – Cord, Darley and Georgianna.

Darley gives up her career for her husband Malcolm to raise two children and harbors a sore spot for her brother Cord who marries the middle class, artist, Sasha who were given Cord’s parents’ house on Pineapple Street to live in. Sasha finds it a bit like an old fashioned gaudy mansion of days of past and is scrutinized for her decisions, wanting more simplicity, by her upper class sister-in-laws and mother-in-law. Sasha tries to be friends with everyone, but her bougie sister-in-laws call her a gold digger behind her back – when clearly, she is not. In fact, her acceptance of signing a prenup (at her mother in-law’s insistence) with lame defense from Cord who fluffs it off as though it was for his own protection, would have been enough to send me packing – especially when his defense was ‘his family comes first’, before his wife to be.

Darley’s husband loses his important job and is afraid to let her parents know. Georgianna is a spoiled young woman who has no understanding about money. She falls in love with a married guy, believing he’ll leave his (pregant) wife for her some day, until tragedy strikes and Georgianna falls into a crazed depression, but her family are too self-centered to even notice until she loses it at Sasha’s baby reveal, and all the ugly truths start coming out.

At the end, the characters begin to recognize their flaws, apologies are made, and poor Sasha finally gets her wish for a brand new home – away from Pineapple Street. This was an enjoyable read, although I didn’t find it humorous, and except for Sasha, I found most of this family unlikeable characters. But that’s what keeps us reading!

©DGKaye2023

64 thoughts on “Sunday Book Review – Pineapple Street by Jenny Jackson

  1. HI Debby, it sounds a bit like what Madeleine Astor had to put up with when she married John Jacob Astor. I enjoyed reading about it in The Second Mrs Astor mainly because of the depictions about life aboard, and the sinking of, the Titanic. I’m not sure if this is for me. I get a bit irritated with poor rich people and their lives.

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    1. Hi Robbie. Yes, I suppose we could relate Sacha to Madeleine Astor. I hear what you’re saying. And if you don’t like snooty characters, then no, you may not want to read this. Although it was refreshing to have Sacha come into the story and bring a few people down a few pegs. 🙂 xx

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      1. Hi Debby, I would like the bits about Sacha. I don’t like to read about people being snooty and unkind to others just because they happened to be born to money. Money doesn’t make you better unless you use it to improve yourself and other people.

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    1. HI Deb. You are so right. I didn’t find it humorous at all. But I was invested in Sacha who was plunged into this dysfunct family. I read to see how she’d end up with this family, if she’d finally speak out and learn to keep them at bay. The ending was satisfying. But yes, over-hype on the blurb. ❤

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  2. Thanks, Debby. Probably not what I fancy reading at the moment, but I’ll keep it in mind. And I agree; we don’t always have to like the characters to want to keep reading. Enjoy the Sunday and the new week ahead!

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    1. Thanks Olga. You are correct. I kept reading to follow Sacha to see if she’d go through with the marriage and learn how to stand up to the Pineapple St. elite. The ending was satisfying. The blurb, a bit misleading. 🙂 Happy Sunday and new week ahead to you too Olga. ❤

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  3. By the title of the book I figured it was humorous. In these times of cruel wars and hateful rhetoric, not to mention SO much violence, the novel appealed to me. However, by the author’s blurb and your own review, Debby, it seemed to me a selfish disconnect of the wealthy.

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    1. HI Carol. Yes, you are right. The blurb is a tad misleading, as I didn’t find humor in this book. And yes, there is plenty of entitlement in this book, something else I don’t care for. But my investment in reading came with Sacha the ‘regular’ girl who’s marrying into the family of entitlement. That kept me reading wondering how she’d overcome her over-bearing rich new family members. Many times I thought she should leave Cord, but somehow, the ending was satisfying. ❤

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  4. I think we all enjoy a good escape read as the real world often becomes more like fiction every day..
    Sounds an interesting interwoven story Debby.. ❤
    Have a wonderful Sunday and may the rest of your New week be peaceful xx ❤

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  5. What an interesting blurb and review, Debby. Like you, I also may miss the humor in this story. In real life, the lack of empathy on the part of the 1% is worthy of despair. Sasha sounds likable, but the rest of them… not so much. Thanks for sharing the interesting book and your thoughts!

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    1. Thanks Diana. Yes, humor is subjective for sure, but I think I happen to have a great sense of humor, and I didn’t find any, lol. Sasha is the true hero who eventually brings those ‘Astors’ down a few pegs. 🙂 ❤

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      1. You do have a great sense of humor, Debby, but you’re also empathic and that makes these kinds of books difficult. The sense of entitlement and unfairness is hard to find funny. Of course, I haven’t read the book, so perhaps I’m wrong here.

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      2. No, you aren’t wrong. And you’re right about my being an empath making me sensitive to painful and wrong things, but yet, I am drawn to stories of hardship and overcoming, underdogs, misfits, and survivor stories. I suppose they keep me feeling and in the end can be inspirational. I continued reading the book because Sasha was a misfit among her new family. I was rooting for her and waiting to see how she handled them, and she did a good job, and so did the author with the story. ❤

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  6. This sounds like a credible escape novel, Debby. As it happens, my web guy has “Stockton” in his name. He also is from old money though he denies it. (Of course, I still pay him for his services–haha!)

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  7. Sounds interesting enough, but I feel like I’d rather read one of your memoirs….. and I will!

    You did an honest review. I like it better than Cynthia D’Aprix Sweeney’s blurb statement.
    💖🤗xxx

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      1. xoxoxo
        Reading your article on the war right now. My heart is broken.
        My husband is of Jewish and Japanese heritage. His last name is Jewish.
        I have been worried about him since the attack on Israel on Oct. 7.
        Anyone with half a brain & some historic knowledge could read the writing on the wall.
        Adore you! Now, back to reading.
        💖xxxxxxx

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  8. At least there was one character you liked! I might find it hard to read if so many aren’t likeable, but I’m definitely intrigued by the book description and your review, Debby 📚

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  9. Thanks for your review, Debby. It sounds like we all would like Sasha but not so much the other snooty characters. Even so, it does sound like a good escape. I find it interesting that you didn’t see the humor, but the book is described as a hilarious debut. I have a feeling my thoughts would be parallel with yours. 🙂 🩷

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    1. Lol, thanks Lauren. I think humor is subjective. I also like to think I have a good sense of humor, lol. An escape read it was last winter while I was away. Sasha kept me going through the book because I wanted to see if she’d learn to stand up for herself – and she does. 🙂 xx

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      1. You do have a good sense of humor, Debby, which makes me feel like my review would be similar. But you’ve hooked me with Sasha now. I just finished reading a book where the main female character was weak and indecisive. I know we all have those moments, but her moments lingered to the end and it bothered me. I almost found myself pleading with her into the pages to be stronger. 🙂 But she changes, though subtle. Anyway, I’ll add this to my list. Have a great day! xoxo

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      2. Thanks Lauren. And believe me, I’ve read about 3 books this year that didn’t cut it for me with same issues – build up to nothing, no growth in character and unsatisfied endings. Hugs my friend. ❤ xx

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