Book Review: “Pineapple Street” by Jenny Jackson

A Classy Novel About Class

Zachary Houle
5 min readFeb 20, 2023
“Pineapple Street” Book Cover
“Pineapple Street” Book Cover

Do you know that old saying that you shouldn’t judge a book by its cover? When it came to picking Jenny Jackson’s Pineapple Street out of the line-up of books about to be published on NetGalley — a platform where publishers give away upcoming books to scribes like me — I was drawn in by the blue-toned cover. I read the description and saw that it was a family drama, so that was doubly appealing to me. Well, the novel is less literary fiction than it is Chick Lit (and I’m not entirely sure how, seemingly by fate, I wind up getting books that are probably more suited to women), but it is a pleasant and pleasurable read. If I can say only one positive thing about this book is that I didn’t want it to end — and I’m hardly in the target demographic for this! It’s a novel about a family that represents old money living in the Brooklyn Heights neighbourhood of New York City and looks at the generation gap between members of said family. It’s also a book about marrying into a higher class in some ways, as well as a novel about white privilege and confronting ideas surrounding social justice. True, nobody is going to associate Pineapple Street with high art, but this feels like an important and ground-breaking novel for what it is. I don’t mean to use this term condescendingly, but Pineapple Street is fluff. But it’s good fluff, and meant for those who like “easy reads.”

The novel is told from the viewpoint of three different women. First, there’s Sasha — who has married into the Stockton clan and is the target of some unnecessary needling and perhaps even bullying from her husband’s two sisters: Georgiana and Darley. Georgiana is a 26-year-old snob who looks down on people and is very immature: she winds up falling in love with a man that she shouldn’t and tragedy results. Darley, on the other hand, seemingly has her head on straighter, but she’s dealing with the facts that her two Kindergarten-aged children are unhealthily obsessed with death and that her Korean husband has lost his high-powered job through no fault of his own. As the story progresses, lessons are learned and the characters begin to appreciate each other more — as well as the lives of those who are less fortunate, particularly those who are living in developing countries. You’ll laugh. You’ll cry. And you’ll come to like the characters who populate this populist novel.

At this point, I’m not so sure what else there is to say about Pineapple Street. This is a novel ostensibly about women for women, even though Jackson lists the odd male as early readers of the manuscript in the acknowledgments section. Still, the fact that this is a book for women isn’t meant to be dismissive. What is impressive about the work is that it treats rich people as fallible human beings. Sure, the clichés abound here of spoiled rich twentysomethings with trust funds in their name who hop from bar to bar getting blitzed as they sample the most expensive champagnes. And, yes, the women of the novel play tennis while the men are known to enjoy a good golf game with $3,000 clubs. However, underneath the surface of this all are people struggling to be loved and who want to make a genuine difference in the world. It’s just that their money blinds them to the notion of being in love with little else than perhaps the pursuit of more money — at least, initially. Jackson has a deft hand in showing characters who grow — even though some of the growth is of the tell, don’t show variety. Yet, although these characters are imperfect, you’ll fall in love with them anyway and you’ll want to know how they turn out once the end of the book is reached. I sense there may be a potential sequel in the making here, though I felt that the novel did conclude on a close-ended note.

If you’re interested in a paring from the other side of the coin — that is, the working-class side — you may want to try the similarly toned Marrying the Ketchups by Jennifer Close. Still, Pineapple Street does do a tremendous job of standing on its own, and showing the rich aren’t composed of heartless bitches and assholes who solely care about money. (Sure, they do care, but some of it has to do with the fact that they are trustees who are trying to make sure that their beneficiaries have ample funds to avoid having to toil in day labour for a living.) There’s a whole lot of love and care that went into Pineapple Street, and it was an eye-opening read for me about people who are willing to change. Once again, this is an enjoyable book that is not going to rack up any major literary awards, but if you’re simply looking for something that’s relatively feel-good and warm, and a book that isn’t going to require you to have a Ph.D. just to parse its life lessons, then Pineapple Street hits the spot. This is a tremendous work of pop fiction that purports to be nothing more or less than a good time — albeit a good time with an important social message — so if you have two X chromosomes and just want a nice, quick read to settle into, Pineapple Street will be your go-to. This is the type of book that is meant to be devoured, and you’ll walk away from it feeling pretty good about yourself. Sometimes, that’s all that you need from a book, so if that cover is enticing, you should know that this is a novel that is well worth your time.

Jenny Jackson’s Pineapple Street will be published by Viking on March 7, 2023.

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Get in touch: zacharyhoule@rogers.com

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Zachary Houle
Zachary Houle

Written by Zachary Houle

Book critic by night, technical writer by day. Follow me on Twitter @zachary_houle.