The Best Version of Itself: Nora Ephron’s New York in When Harry Met Sally…

Meg Ryan and Billy Crystal in When Harry Met Sally, written by Nora Ephron and directed by Rob Reiner

Columbia Pictures

Nora Ephron invented fall. A sweeping generalization, of course, a wild assertion, to assign an entire cinematic season to one filmmaker, as if many others haven’t done it equal amounts of justice, as if other seasons cease to exist in Ephron’s films. Okay, an adjustment: Nora Ephron invented fall in New York. Still a reach? Maybe. But when you think about fall on film, chances are you think of Nora Ephron, and when you think about the films of Nora Ephron, it’s pretty likely you’ll think about fall.1 See what I mean?

I’ve spent 10 falls in New York, a number I believe is large enough to finally grant me permission to officially call myself a New Yorker. Each of these falls—when the air turns crisp and store windows begin to fill with leather jackets and wool sweaters in varying shades of reds and oranges and browns—I swear that this will be the year I buy my Sally Albright Outfit. And each year I fail, surprised to find that it’s suddenly November and there are no slacks hanging in my closet, or quirky printed turtlenecks, and that it’s too cold to stroll the city in nothing heavier than a herringbone blazer. Still, each year, I walk or run through Central Park multiple times a week, consistently marveling at its beauty as if for the first time, stopping to take photos of changing leaves as if I have never once seen foliage. But even at its best, it never looks quite as good as it does in When Harry Met Sally. The trees are never so perfectly uniform orange, never so vibrant all at the same time without a few still-green stragglers. The paths are never that absent of tourists, the dead leaves never that thick and crunchy under your feet. The autumnal park on display in When Harry Met Sally is, if not a version of the city I arrived too late to witness, then perhaps one that even in its own time was more of a dream-like version, a Facetuned glow up, a Ludwig filter on reality. 

There are plenty of standout shots (and lines) in When Harry Met Sally, a film thoroughly committed to showing New York at its best and most inviting. However, it’s this frame—so iconic that it graces the DVD cover and practically fills the entire first page of Google image results for the film—that has taken up permanent residence in my brain. After all this time living here, I know it is a fictional portrait I should dismiss for its ever-so-slight disconnect. Instead, as time goes on, my love for it only deepens. No longer does it look like a fantasy viewed through the eyes of a child growing up in the suburbs. Ten years in, it looks just like the distorted version of the reality in which I live; if love can make people more beautiful in our mind’s eye than they are in real life, can’t the same logic be applied to cities, too?

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When Harry (Billy Crystal) and Sally (Meg Ryan) meet—again, for the third time actually—in a bookstore on the Upper West Side, they meet as New Yorkers, real New Yorkers, having just crossed the 10 year threshold themselves. They’ve each grown since those past encounters; they’re no longer two strangers unable to understand, much less tolerate, differing opinions, no longer ambitious young professionals foolishly thinking they can have it all. All these years later, with breakup-bruised egos and matured perspectives, they truly meet cute. And while their fast friendship this time around is likely a sign that they are meant to be together, I read it another way. Now that Harry and Sally are real New Yorkers, they must know that real New York friendships are often formed at a rapid pace, just as quickly as the city moves, and more often than not over the course of a marathon fuckaround day. 

At the mercy of public transit, New Yorkers are obsessed with time and distance and how to best optimize both. The fuckaround day, though, is the perfect kind of New York day—one where all thought-out plans are abandoned. How perfectly Nora (yes, we will be on a first name basis for the rest of this piece) captures it here, the small simple pleasure of spending an entire impromptu afternoon with someone else you are truly vibing with. Harry and Sally’s reunion is the rare moment of sustained connection when you find yourself too engrossed in conversation to look at your phone or pretend that you have somewhere else to be, ending the day absurdly closer than you started, saying your goodbyes with a bit of reluctance, more because you want to save room for next time than because you want to actually part ways. By the time we reach the scene here in Central Park, where Harry and Sally share intimate details of their most neurotic dreams, they’ve only been friends for a couple of months at most. 

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Rob Reiner directed When Harry Met Sally, and while it’s imbued with the same sensibilities his most popular comedies share—smart and fair, sweet but a little tough, unreliant on cheap gender stereotypes—it’s Nora’s movie, through and through, in its presentation of New York. When Harry Met Sally is a love letter to the city, the kind we’d see again in some of her later directing work (This Is My Life, You’ve Got Mail), a big, gentle hug for its neighborhoods and its people. 

The New York seen through Nora Ephron’s eyes is romantic and idealized—a dream of New York, created in the aftermath of a long stretch of time during which the city was perceived as something more akin to a nightmare—but always quotidian, always (seemingly) attainable. Critics are right to point out that her mostly Upper West Side-dwelling protagonists are white and privileged; but, looking back, aside from Joe Fox, they weren’t particularly wealthy so much as solidly middle class with normal people jobs and relatively modest, rent-controlled apartments. It’s Nora’s warm, comfortable, lived-in New York I have been chasing all these years—not, like many young women of my generation, Sex and the City’s or, god forbid, Girls’. When I watch Harry and Sally stroll through Central Park, I think, If I could just find a way to crawl inside this movie, inside this New York, I could be a real person. I could be okay

Because nothing truly bad, nothing truly awful ever really happens in Nora Ephron’s New York. Her New York is a place where, as Sally Albright says, you go so something can finally happen to you (including but not at all limited to meeting the love of your life). In Nora’s New York, there are no corrupt cops or empty luxury high rises for tax-evading oligarchs, and no one, not one single person, complains about cyberbullying the mayor. 

That’s not to say nothing bad happens; things do indeed get rotten. But if “everything is copy” was the first guiding principle of Nora’s life, “I insist on happy endings” was the second. The point is that it’s all survivable; it will all be a funny story at some point in the future.

Nora Ephron was born in New York, but she was not raised there, returning permanently (save for a very famous, very brief stint in Washington, D.C.) only as an adult—an inevitable fate which, as she later wrote, she’d spent her Beverly Hills childhood waiting for. In those in-between years, the only New York she knew was the one that existed in her mind: “the most exciting, magical, fraught-with-possibility place that you could ever live; a place where if you really wanted something you might be able to get it; a place where I’d be surrounded by people I was dying to know; a place where I might be able to become the only thing worth being, a journalist. And I’d turned out to be right.” Of course she was right; she’s Nora Ephron, the woman so invested in the magic of New York she wrote a love story about her (not-that-great, actually) apartment. 

While Nora was from California, she never really belonged there; she was imbued with a New Yorker’s sensibility and devotion all along: arch and opinionated, with little patience or interest in froth. It makes sense, in a way, that all of her films set in the golden state were bombs. There’s no love for their location; unlike her New York films, in which the city is just as much a character as the actual characters themselves, they could likely be set anywhere without losing much. Even in the best of the uneven bunch, there’s something tonally off; despite the romanticism in her scripts, they are still full of sharp barbs and a touch of cynicism that cannot survive under the bright California sun. (Case in point: A dark holiday comedy set at a suicide prevention center in…Venice Beach.) It’s when she turns her eye to New York (even just partially, like in Julie and Julia, or for a pivotal plot point, like in Sleepless in Seattle) that her films feel most comfortable, most relaxed, most right.

It’s this outsider-turned-insider perspective that makes her on-screen depictions of the city work, a combination of her dream and the reality she encountered. No matter how many ugly truths she encountered as time went on, she still saw the best in New York. Money helps, of course it does, but it doesn’t completely immunize a person to a city’s challenges. This year alone served as proof: plenty of New Yorkers wealthy enough to live comfortably will still inevitably bail for greener pastures.   

Seeing Harry and Sally create entire lives for themselves in the city, far from where they started, and become real grown-ups argues otherwise. The truth is that New York will always treat you better the longer you stay. You just have to spend enough time getting to know the rhythm of the city, learning how to play it like the instrument that it is, accepting that you’ll still hit a few bum notes here and there, but knowing the ways to wring it for as much as it can possibly offer, money or not. In the end, it shakes out to become just the place you live, a place you love as much as anyone else who loves the place they live, personally special not so much because it’s New York but because it’s become well-worn and known and wonderful in an indescribable way. Because it’s home. Nora’s depictions of modern adulthood here understand that, particularly emphasizing the high-low combination of joys this city has to offer. Her version of romanticizing New York doesn’t mean showing off its flashiest features; it means finding charm in day-to-day life, especially the cheap thrills. Harry and Sally dine out, they go shopping, they go to formal parties with open bars—but they are at their closest and most intimate when it’s just the two of them and the simple gifts this city has to offer: being the only people in a wing of the Met; enjoying a really great sandwich in a crowded deli; walking through Central Park in its full fall glory.

This summer and mild fall, as Central Park became a vital location for both solitude and socialization, I thought often about Harry and Sally and their walks and talks. Why did people stop doing that? When did every conversation or meet-up with a friend shift to occurring over drinks or dinner in a just too-loud and just too-dim bar or restaurant where it was impossible to really get close? I thought about how suddenly we were forced back out into the fresh air, into the one anomalous chunk of nature plopped smack dab in the center of this concrete island, feeling safe and really seeing each other once again. 

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Nora Ephron and I only lived in the same New York for a little over a year, though, of course, we didn’t really inhabit the same New York. I was a poor student downtown, she was a famous filmmaker uptown. We did share one thing, however: Central Park. New York’s park. Harry and Sally’s park. Our park. I like to think she delighted in its small wonders her last year here: the reservoir regulars who start running laps at the same time every morning, no matter how cold; the few short weeks in spring when you can smell old ladies’ perfume lingering in the air; the way bare backed bodies spread out across Sheep Meadow on a hot summer afternoon resemble a painting; the perfect afternoon walk by the history museum when the leaves begin to turn. 

I miss Nora Ephron. I know it’s such a strange thing to say about someone I never even met, but it’s true, and I feel it more acutely as the years go by and the city seems to grow increasingly crueler and more difficult to love unconditionally. I still don’t live in Nora Eprhon’s New York; I have been made aware of this countless times over the past decade. I don’t think I know anyone who does though, really. Despite having a reasonably good job, I can’t afford to live on my own or meet my friends for lunch at the Boathouse and I have never been to a party with my peers that wasn’t BYOB. The real New York is not, of course, Nora’s New York. But it’s still nice to pretend sometimes, nice to put my headphones on, queue up my Nora Ephron soundtrack playlist and walk through Central Park on one of the last perfect days of fall before the trees are skinny and bare, and for an hour or two pretend I am the plucky heroine in one of her New York films. It’s nice sometimes to tell myself that the good days here outnumber the bad, that everything will work out okay in the end, because it has to, because it would simply be bad writing for it to not.  

  1. It has to be said…Sure, you think about Woody Allen, too; upon When Harry Met Sally’s release in 1989, many critics dismissed it as cheap imitation. Both paint chatty portraits of a mostly white, uptown, neurotic New York, but the similarities end there. Ephron takes a warmer, more optimistic approach. Allen’s films, meanwhile, are more caustic, often told from the perspective of a misanthropic man with a thoroughly jaded view of modern love.