Playwright and author Lila Raicek, who grew up in Connecticut, has left New York twice since she came to Barnard to study writing as an undergrad. A decade ago, she spent a couple of years in LA when her play Vertebrae was optioned, and she wrote for Darren Star’s Younger, plus other shows like Gossip Girl. (She’s currently adapting Vertebrae into an erotic thriller TV series called Night Float with Nina Dobrev.) And last year, she spent time in London when her play Master Builder starring Ewan McGregor and Elizabeth Debicki was on the West End. Her recently published debut novel, The Plunge (Park Row), was informed by her post-Hollywood return to New York and the uptown apartment of a mentor. Two of her fictional characters, Liv and Damon, "fall into a tumultuous affair that plays out across museums, park walks, and sultry midnights in Manhattan,” she tells Vogue, “specifically the Upper East Side, the neighborhood itself transforming into a furtive hideaway. In many ways, The Plunge is the love letter to New York that I’ve always wanted to write.” Here, her many affections:

Hotel: I can’t not pick The Carlyle. Ludwig’s murals of redheaded Madeline at Bemelman’s, the dark glitter of the skyline if you manage to crash a party upstairs. Once, I wandered in alone to use the bathroom while inconsolably crying over a breakup, and a waiter snuck me into a Judy Collins concert at Café Carlyle. I cried even harder when she sang a melancholic cover of “Who Knows Where The Time Goes,” yet it remains a fond NY memory.

Restaurant: When I was a grad student, I workshopped a play at the Cherry Lane Theatre and we’d go next door to Commerce afterward for drinks until closing. Over a decade later, it reopened as Cafe Commerce uptown and brought that sapphic mural of Saint Sebastian with it. The new iteration has an intimate French bistro vibe, and it reminds me of when I was a wild theater kid.

For breakfast: Grab a cinnamon croissant at Birley Bakery or a lox bagel at Eli’s and eat it on a bench near the serene Conservatory Water with its model boats.

For a caffeine fix: Via Quadronno, a charming spot, is featured in the penultimate scene of the book. Strong Italian cappuccinos in winter, and gelato cones in the summer. (Hint: Their sferzata di salute soup has kept me alive in dark times.)

For dessert: Café Sabarsky, the Viennese café nestled inside the Neue Galerie, is a romantic-date dessert dream, with a grand piano and an array of decadent “tortes” lining the mirror. Order the sachertorte with a glass of wine, but add a warm pretzel for good measure.

Late-night diner: J.G. Melon for old-school burgers, martinis, and red-checked tablecloths. Bring cash!

Theater: Not only is the Park Avenue Armory a momentous landmark—it was an actual nineteenth-century military fortress—but it also houses an astounding range of performing and visual arts. I’ve recently seen Lorca and Ibsen adaptations, an unhinged Schubert opera, and I always catch TEFAF, the art fair, in May.

Best dish: Maybe not best, but pro tip: the off-menu Cajun chicken with fries at Le Charlot.

Must shop: Another nod to the Neue Galerie. After you absorb the luminous Klimts (Damon takes Liv here to see the haunting “Portrait of Ria Munk III”), don’t miss the shop downstairs with Austrian and German treasures. I found a special edition of Joseph Roth’s The Coral Merchant, which served as a fictional spark for (spoiler)... a murder weapon.

Place I always visit: When venturing beyond uptown, and you should, shout-out to quintessential Tribeca osteria Locanda Verde (my cousin’s place!)

To see art: The gallery scene is not to be missed. In recent years, I’ve discovered the brilliant work of Karyn Lyons at Turn Gallery, whose painting “The Imposter” became the star of my book cover, and also Vivian Springford at Almine Rech. The vibrant Matisse show at Aquavella on right now is worth catching.

To stock up on beauty buys: Zitomer, an iconic 70-year-old pharmacy mecca. I’ve cried here before, too, but it has never once stopped an elderly saleslady from scolding me that my pores need help. Also, the new Violet Gray, chicly tucked away in a garden.

Bookstore or library: One of the last of its kind, The Corner Bookstore is a cherished gem of Carnegie Hill, open since 1978! I visited often while writing this book as a literary haven. The New York Society Library is also a special place.

To buy flowers: I always pause in front of the lovely sidewalk flowers at Alexander Florals.

Must-take Instagram shot: Maybe the new Le Petit Prince sculpture? Or the hot dog cart in front of the Mark Hotel.

Must-buy souvenir: Black-and-white cookies at William Greenberg! Also, Poems of New York is a perfect, pocket-sized anthology (I worked for the editor in college) that I gift to everyone.

Tourist trap I love anyway: The Guggenheim Museum.

Nature escape: Central Park is a leading character in my book, and a boundless source of inspiration that I have returned to again and again throughout the volatile weather of my life. I walk at all hours, in all seasons, and my route reflects my mood: the sundial in Shakespeare’s Garden, the floral urns of Bow Bridge, the bronze angel atop Bethesda Fountain. I remember drifting through the saffron-hued corridors of Christo’s The Gates in 2005 and realizing I could never leave this city.

For peace and quiet: If I reveal the Lehman Wing at the Met Museum, will I regret it? The Bonnards, the Balthuses, the red-velvet sitting room and stained-glass skylight...it’s a hushed respite to reflect and escape.

Best way to get around town: By foot, of course! And I do love a crosstown bus.

Day trip: The Plunge travels to the North Fork of Long Island, which has long been a home for artists and writers. Wine-taste your way through the many vineyards, hike along Orient Point, and eat at The Old Mill Inn in Mattituck.

Best view: The top of Belvedere Castle at twilight, waiting for the moon to rise over the skyline.

Architectural gem: The newly renovated Frick Collection, based in Henry Clay Frick’s 1914 mansion, is a beauty. I’m sad that Flora Yukhnovich’s “Four Seasons” is gone, but sit beneath the glass-domed roof in the Garden Court and find Whistler’s gossamer portrait of Frances Leyland.

Best time to visit, weather-wise: Cue Billie Holiday’s “Autumn in New York,” but don’t miss the park smothered in pink confetti from the cherry blossoms bursting in Spring.

Must-skip/don’t bother: If there’s a line for frozen yogurt...

Workout: Looping endlessly around the Jacqueline Kennedy Onassis Reservoir. My best friend and I call them “despair walks.”

Cheap date: The concerts at SummerStage, and the French film festival Films on the Green—both free and outdoors in Central Park. And, always, Shakespeare in the Park, if you wait in line for tickets!

Worth-it splurge: Dining beneath Joan Mitchell’s “King of Spades” at Marcel, the new restaurant inside the brutalist Breuer building that now houses Sotheby’s. I’m a bit biased because I got married at La Mercerie in Soho (where we lived for 2 years), so I’m in awe of anything that Robin and Stephen Alesch design—and their latest is elegantly enchanting.

Best place for people-watching: The bar at Polo Bar, sorry. (Hi, Nelly!) A favorite sighting was [Aryna] Sabalenka right after she won the 2025 US Open.

Secret spot only locals know: Albertine, named after a Proust character, is a charming French bookshop tucked inside a Beaux Arts mansion. The hand-painted celestial ceiling, wreathed with gilded zodiac signs, is transporting, as is its selection of French poetry.

Spa or salon: I rarely have time (endless deadlines!), but recently, before a photo shoot, a friend sent me to Georgia Louise, who depuffed me in ways I didn’t know were possible.

Favorite film about New York: There are many to choose from, but the 1964 film The World of Henry Orient blissfully captures another era–and gets a mention in the book. (I first watched it with my mom.) There’s a classic scene in Central Park when the teenage girls spy on Peter Sellars at the Alice in Wonderland statue, but I often think of the heart-twisting shot when Val traverses a snowy, funereal field all alone.

Something you should know about my city: While it’s gained new attention, the Upper East Side has had an unfair rap. Particularly when I was a single, struggling playwright living in rent-controlled garrets, I was always dazzled by the rich tradition of female writers who once lived and wrote here: Sylvia Plath, Shirley Hazzard, Dorothy Parker, Wendy Wasserstein. And of course, Joan Didion, who described living in a “monastic” place uptown in her infamous essay. I love this line: “I remember walking across Sixty-second Street one twilight that first spring, or the second spring, they were all alike for a while.”

How this city influences my writing: New York is inexorably in motion, it’s febrile, feral, and kinetic. I love disappearing into the carnival of strangers, while remaining attuned to the wild, unexpected moments in the everyday. I wrote most of The Plunge while alone in the city during the pandemic, inspired by how tenaciously it pressed on during its darkest hour. For a writer, the tensions of New York—grit and glitter; chaos and solitude—provide a charged space in which stories can take hold.