8 of the Best New York City Meet-Cutes in Literature

I moved to New York in 2010. When I left two or three years later, a friend asked me what my best moment here had been. I realized I had no snappy anecdote; instead, what I thought of were those times when I was on my own, well-caffeinated, and walking somewhere above Canal and below 14th. Being in Manhattan on a big-skied day can feel insanely exultant, outrageously full of potential.

The prime intoxication of any city is the probability of chance encounter, but this feels exceptionally heightened in New York City, a place of intersections both literal (it’s really a giant grid) and figurative (there’s coincidence to be had in a population of 8.5 million and counting.) My debut novel, Neon in Daylight, is plotted around chance encounters on downtown streets, but it’s also driven by the romantic, reasonable idea that you might meet anyone here, that they might change your life. The literature of the city is filled with moments of connection, coincidence, and confrontation on its streets. Here are a few of the best.

“Wants” by Grace Paley

Brief and guileless as a shrug, Paley’s story packs the enormity of regret, affection, marriage, personhood into fewer than 800 words. Its first three sentences are incidental and monumental: “I saw my ex-husband in the street. I was sitting on the steps of the new library. Hello, my life, I said.”

Breakfast at Tiffany’s by Truman Capote

There are few more fascinating strangers than Holly Golightly, and she’s particularly appealing when glimpsed by the novella’s unnamed narrator, from a Fifth Avenue bus stop: “I noticed a taxi stop across the street to let out a girl who ran up the steps of the Forty-second Street public library. She was through the doors before I recognized her, which was pardonable, for Holly and libraries were not an easy association to make.”

“Debbie Harry at the Supermarket” by Wayne Koestenbaum

In Manhattan, the stranger ahead of you in line might also be a generation’s icon. However many times I walk past the grand old Chelsea building where Debbie Harry still lives, I will always think the words “Debbie Harry at the Supermarket.” Koestenbaum, crushing wildly, spins a roaming ode of an essay precipitated by spying the Blondie singer ahead of him, waiting to buy groceries. The ensuing rhapsody includes this observation: “The terror of being unable to describe Debbie Harry’s sublimity is built into the experience of apprehending it…” Stars: they’re nothing like us.

“The Purchase” by Elizabeth Hardwick

An author sometimes needs to incite her characters into collision, and Hardwick knows that life’s putative chance encounters can also be semi-orchestrated, half-willed. The magic of chance in this story is more the contrivance of the character himself, Palmer, who heads downtown with the intention of running into an acquaintance’s wife — and succeeds, cranking the story’s gears into motion. (There is the added pleasure of imagining moneyed Hudson Street as a place where, “a dingy, unkempt, transient quality still clung to the neglected alleys.”)

Jazz by Toni Morrison

“Romantic love seemed to me one of the fingerprints of the twenties, and jazz its engine,” Morrison wrote of her sixth novel, in which the city, an extra engine to the jazz, is unnamed but unmistakably New York—specifically, 1920s Harlem. The central couple, Joe and Violet, arrive together, but it’s in the city streets, which Morrison riffs on in bursts like sax solos, that they encounter themselves and each other for the first time: “The minute they arrive at the train station or get off the ferry and glimpse the wide streets and the wasteful lamps lighting them, they know they are born for it. There, in a city, they are not so much new as themselves, their stronger, riskier selves. And in the beginning when they first arrive, and twenty years later when they and the city have grown up, they love that part of themselves so much they forget what loving other people was like — if they ever knew, that is.”

Dancer from the Dance by Andrew Holleran

The first line of this unashamedly lush and lyrical 1978 novel, an under-celebrated gay classic, announces itself as a novel of crowds, glances and aleatory romance: “He was just a face I saw in a discotheque one winter…” That face is Malone’s, a character who commits to love in the grand abstract after a random, but longed-for encounter with a messenger boy, a Puerto Rican kid from the Bronx, a kind of cupid in “maroon pants and sneakers.” “Little wonder,” that when Malone, “looked at strangers on the street now, his unquiet yearning for rescue went out to them.”

Just Kids by Patti Smith

Smith’s celebrated memoir of her relationship with Robert Mapplethorpe includes the memory of meeting him on her first day in the city. A chance meeting in Brooklyn is also an instantaneous enchantment: “I watched him as he walked ahead, leading the way with a light-footed gait, slightly bowlegged. I noticed his hands as he tapped his fingers against his thigh. I had never seen anyone like him. He delivered me to another brownstone on Clinton Avenue, gave a little farewell salute, smiled, and was on his way.” Days later, he walks into the bookstore where she works. The rest is punk history.

Underworld by Don DeLillo

The greatest novel DeLillo ever wrote, which is also one of the greatest novels anyone ever wrote, is shot through with the electricity of street encounters. The most significant is one of plain eros. Klara Sax, unhappily married, artistically frustrated, sees Nick Shay standing by a lamppost from her window. He sees her, flicks a cigarette, walks across the street and the thing is begun: an affair, a plot.