A Pineapple Partnership

When someone writes a book inspired by the same Brooklyn street that helped launch your own brand and blog, it feels like content kismet. Especially when that book, Pineapple Street, is as juicy as the fruit itself—a fast favorite this spring among team Dudley! We asked author Jenny Jackson to share her evolution from editor to writer, and what inspires her most about the borough she and her characters call home.

Your book has the feel of a great social novel from the past—the Gilded Age or the Roaring 20s. What authors have inspired you?

Of course Edith Wharton and Jane Austen are foundational (There is a bit of Darcy and Elizabeth in Curtis and Georgiana!), but my true writing idol is Laurie Colwin and her hilarious novels of love and family in New York.

You recently speculated that if doctors are the worst patients, book editors might be the worst authors. But what about your “day job” as a longtime editor made it easier to write Pineapple Street?

I’ve learned an incredible amount from the authors I publish. From J. Courtney Sullivan, who wrote Maine and Commencement, I learned about writing from a rotating point-of-view. From Kevin Kwan, author of Crazy Rich Asians, I learned how to turn up the volume on a place so that a city can almost become a character. And from Katherine Heiny, author of Early Morning Riser and Games and Rituals, I learned how to build a joke. I feel like I’ve taken a 20-year writing course from my authors! 

There’s a lot of satire in your book (“She felt like she’d been delivered terrible news…like avocados caused cancer.”). Is humor something you look for in your authors’ books?

I’ve long believed in books as medicine. I think we read for different moods, we read fiction to give us what we need at any given moment. I wrote Pineapple Street in 2020 and 2021 when things felt pretty bleak. I wanted to give readers a sense of joy with the book and I really wanted to make people (and myself!) laugh. As an editor, I feel like I try to publish a range of fiction and while I do feel myself drawn to humor, I can also fall in love with books that fill other needs!

Who’s your favorite Stockton family member?

Nobody agrees with me, but Georgiana is my favorite. I like to think of her as my “delightful brat.” At the beginning of the novel she really has no self-awareness at all, but she grows a lot. Since she is the youngest she really feels things intensely, especially the madness of first love, and it was fun for me as a writer to get caught up in her passion and heartbreak. 

If and when Pineapple Street goes to film, who are your ideal actors to play your characters?

I love Jake Lacy from “White Lotus” season one for Cord. Then Eve Hewson (Bono’s daughter and the star of “Bad Sisters”) for Georgiana. Then Daniel K. Isaac from “Billions” for Malcolm.

What’s the biggest surprise about having your book out “in the wild” in readers’ hands?

I’ve been so surprised and moved by the conversations people have shared with me. I think that no matter how you grew up, money is a big part of family life. Maybe your grandmother left a ring for you and somehow your sister ended up with it. Maybe your grandfather gambled away the house when you were a baby. Maybe your mom hides shopping bags behind the study door so your father won’t see them (yeah, Mom, I see you). Everyone has money stories and it’s been incredible to have friends and readers share those stories with me. 

What’s your favorite spot in Brooklyn?

There is a wonderful little bar in the fruit streets called Inga’s Bar. It gets really crowded, so you have to arrive right at 4:59 if you want to scoop up a seat for a cocktail, but it’s fabulously atmospheric and fun. Then, for healthier days, I love running across the Squib Park Bridge. It takes you from the promenade of Brooklyn Heights down into the Brooklyn Bridge Park. The little bridge weaves between buildings and then suddenly presents a view of downtown Manhattan and the Statue of Liberty that feels magical. 

Do you have a favorite Dudley?

I fully respect those people who wear pajamas to the airport, but I just know that the day I do I will end up running into an ex-boyfriend at security. I love the Greenpoint Boatneck for travel because it feels as cozy as a sweatshirt, but if you run into that guy who never let you order the same entrée at dinner, you’ll look fantastic.

Are you an Orange, a Pineapple or a Cranberry (IYKYK)?

I wish I were a pineapple, but I know I’m an orange!