It’s hard to believe this witty, incisive, unputdownable novel is Jenny Jackson’s debut. Pineapple Street follows three women in an old Brooklyn Heights clan: one who was born with money, one who married into it, and one who wants to give it all away.
Darley, the eldest daughter in the well-connected, carefully-guarded Stockton family, has never had to worry about money. Darley followed her heart, trading her job and her inheritance for motherhood, sacrificing more of herself than she ever intended. Sasha, Darley’s new sister-in-law, has come from more humble origins, and her hesitancy about signing a prenup has everyone worried about her intentions. And Georgiana, 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.
Neither my partner nor I have enough wealth to even warrant a conversation about a prenup, and I’ve never lived in New York. And yet, I found myself relating deeply to each character as they navigate difficult life choices about how they want to show up for their families and communities. Full of recognisable, loveable – if fallible – characters (and a few appalling ones!), Pineapple Street is about the peculiar unknowability of someone else’s family, the miles between the haves and have-nots, and everything in between.
Rife with the indulgent pleasures of life among New York’s one-percenters – glittering parties, weekend homes and hungover brunches – Pineapple Street is a scintillating, escapist novel that sparkles with wit and wry humour. But alongside the fun escapism of this ultra-wealthy setting, with the glitzy tennis club meetups and the didn’t-need-to-check-the-price-tag fashion ensembles, there is also a satisfying layer of social conscience. Couched within an engaging romp, Jackson asks us to consider pertinent questions about today’s society: how do wealth, capitalism, race and privilege shape our experiences, and what can we do to change it?
Reading this novel is a bit like having brunch with that friend – the one who isn’t afraid to dig into the nitty gritty topics and challenge everyone at the table to broaden their perspectives, while still managing to have a hoot of a time.
Pineapple Street is the perfect book to curl up with when you feel the need to inject a micro-vacation into your Saturday afternoon. I tore through it in a weekend, with a smile on my face and a renewed appreciation for tablescapes.






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