A Story of Sisterhood: Read a Q&A from Jenny Jackson, Author of Pineapple Street

Briefly tell us about your book.

Pineapple Street is the story of three sisters in the same wealthy Brooklyn Heights family. Darley, the eldest, was born with money. Sasha, the in-law, has married into money. And Georgiana, the millennial conscience of the family, wants to give it all away. It’s a story about family, love, heartbreak, secrets, and how to live a decent life in this world.

What inspired the idea behind this book?

My little family of four spent much of the pandemic living with in-laws; my husband’s parents in Connecticut, and my parents in Massachusetts. It was amazing in ninety-nine ways—they helped with Zoom school and childcare, we had movie nights and long hikes in the woods—but it was also really funny to see how different our families of origin sometimes felt. I tease my in-laws about their plants (I think they must have two hundred plants in their house. They take pictures of them and call them their “grandbabies.”) and I know my husband is mystified by my parents’ crazy art collection (They have tons of friends who are painters and some of their art–like the stuff featuring naked people and cats–is pretty weird.). So, I wanted to write about that funny feeling of being an outlaw among your in-laws, that feeling that no matter how long you are married you’ll never really get the plant-thing or the naked-people-with-cats-art-thing—you’re never really one of them.

If I looked at your internet history, what would it reveal about you?

You would definitely know I had two young children! You would find a page devoted to pink eye and a Google search for “What is a rare Pokémon?” But then you might also know I was about to go on book tour because you would see internet results for “how to do eye makeup that does not look crazy” and “can I wear two pairs of Spanx at once or will I get a stomachache?”

What are you hoping the reader will take away from reading your book?

I’d like for readers to feel a sense of joy. I hope they will see that these very flawed, occasionally ridiculous people are a family bound by love, all doing their best to evolve in a changing world, all trying to be good. I have a soft spot for even my most spoiled and ill-behaved characters, and I hope you will too. I hope it makes readers laugh.

How did you think of the title of the book?

I was actually living on Pineapple Street in Brooklyn Heights. It’s such a funny neighborhood in that it’s both very fancy and also very normal. There are lots of celebrities that live here, lots of finance types with black cars sweeping them away, and on the weekends the air is filled with the thrum of helicoptors that take them off to the Hamptons to their country houses. But at the same time, it’s a neighborhood of playgrounds and churches and bagel shops. I became fascinated by a few spots in Brooklyn Heights: The Casino which is a members-only squash and tennis club; the St. George Hotel which was once the most glamerous hotel in New York City and now houses a gym and a college dorm; and the pre-school where all the richest, most traditional families send their children. For some reason I didn’t know the title as I was writing the book, but once I finished I realized it had to be “Pineapple Street.”

Do you write about people you know? Or yourself?

I have to admit that most of my comic inspiration comes from my friends and family. There’s a scene in the novel where the children carry around a dead pigeon in the park—my kids did that. There is a scene where a child swallows his aunt’s baby teeth and my friend’s child did that. From the dog who throws up the lacy underwear to the caddy appreciation day, much of the comedy here has been stolen from real life.

What are you working on at the moment?

For my next novel, I’m leaving Pineapple Street and heading to my hometown of Ipswich, Massachusetts for a story about marriage. Ipswich is famously the home of John Updike and the setting of his novel, Couples, and when that book was published it scandalized the entire town. I’m drawing a lot of inspiration from his legacy but definitely hoping to avoid scandalizing anyone!

Buy a copy of Pineapple Street here.