When Harry and Sally met New York City

Twenty-five years after the classic rom-com debuted, the film’s Manhattan locations remain an ideal tour for visitors and locals alike.

“Nothing has happened to me yet. That’s why I’m going to New York!”

Bright-eyed, '80s-hair college graduate Sally (Meg Ryan, at her peak) perkily uttered that enthusiastic assessment of big city life to Harry (Billy Crystal, at his) during the opening road trip of 1989’s sincerely rom-, indisputably com classic, When Harry Met Sally… and she wasn’t wrong. Everyone knows New York is where things happen, and the film’s Manhattan had never looked more happening. Even 25 years after its debut, the movie has everything: autumnal walks in Central Park, huge apartments with impressive views, fake orgasms over impossibly thick pastrami sandwiches.

In fact, the beautiful montages and key locations in the film are so quintessentially New York, they serve as a perfect itinerary for new and frequent travellers alike. Even locals could benefit from an occasional When-Harry-Met-Sally tour – say, every five years – to rekindle their love of the city.

So cue up the Harry Connick Jr, grab your bowler hat and, if you’re lucky, someone you love: we’re going for a (non-sequential but geographically logical) walk!

We’ll start with some fortification at the single most important landmark on this film tour: Katz’s Delicatessen on Houston Street, which marks the line of demarcation between the East Village and Lower East Side neighbourhoods, both of which are currently too hip to be Harry or Sally friendly.

This 125-year-old deli is the stuff of corned beef legend. The lines getting in (to order) and out (to pay) can be long, especially on weekends, so you may want to expedite your lunch by sitting at a waiter-served table – but then you wouldn’t be sitting at the table, in the self-serve section. In the middle of the main dining room, indistinguishable from every other except for the sign hanging above it, is the table where Sally hilariously and provocatively demonstrates the ease and ubiquity of faking an orgasm – to which Rob Reiner’s mother famously quips: “I’ll have what she’s having.”

I joined a tourist who was eating alone at the table, and he romantically shared the plate of dill and garlic pickles that’s delivered to every group. As he packed up the uneaten half of his massive, expensive, mustard-smeared pastrami on rye, he seemed oblivious to the diners taking his picture (though they were really aiming for the sign). I asked if he chose the table because of its connection to the film.

“What’s a ‘Harry meets Sally’?” he asked.

I gave him a summary and his eyes went wide in recognition. “Oh! The scene with the…the…Oh! Well, I’ll be damned!” And then he promptly handed his phone to a stranger – who’d just snapped a picture of the sign – to capture his accidental brush with cinema fame. He left and a pretty blonde took his place. She was a few bites into her sandwich, which she wisely carved into with a fork and knife, when an older gentleman paused to flirt with her: “I’d be glad to have what you’re having.” She looked perplexed, so I pointed out the sign above her. She guffawed at her cluelessness.

After finishing my sandwich, a creamy slice of New York cheesecake and a terrible cup of coffee, I asked a waitress how often people ask for the famous seat. “Way less than you’d think,” she said. “Maybe two or three times a day. Most people have no idea.” She said she could only think of one occasion in the last two years when someone recreated the scene. Then she proudly pointed out a faded, 25-year-old photo of the cast during the filming, next to another of Reiner unappetizingly eating a sandwich.

Roughly eight blocks west, at the corner of Houston and Lafayette Street, is the Puck Building, its facade perhaps more recognizable as the office from the US sitcom Will & Grace. Inside, two key When Harry Met Sally… scenes were filmed: the wedding of the couple’s best friends Marie (Carrie Fisher) and Jess (Bruno Kirby), in which Harry and Sally have a big row and call off their budding relationship; and the New Year’s Eve Party where (spoiler alert) the two reconcile and decide to spend the rest of their lives together. The wedding took place in the Grand Ballroom, which is now an REI store selling outdoor sports gear. The party was filmed in the Skylight Ballroom, now a private office space.

A few blocks up Broadway and two blocks west is the second most famous park in Manhattan. Washington Square Park appears twice in the film: early on when the eponymous couple first part (“Have a nice life,” Sally said before Harry walks off under the white marble arch) and again at the end (a callback to the earlier scene). The small-ish park is cinematically lovely any time of year, especially since playgrounds were added and the fountain was moved five years ago to be aligned just so with the arch. Sally would approve.

Since there’s nothing worth seeing between Greenwich Village and Central Park – at least according to Reiner’s version of the city  – you might as well hail a cab. The subway would take you to our next stop as well, but Harry and Sally never venture underground, it seems.

Head straight to the inviting Shakespeare and Co Booksellers, unrelated to the older ones of the same name in Paris. This is the last of a small chain, the original of which closed on the Upper West Side in 1996, and was where Harry meets Sally for the third time after Marie spots him staring at her from the "personal growth" section. The bookstore doesn’t specialize, so has a bit of everything, including “World Film Locations: New York”. Plot-wise (and tour-wise) the bookstore scene is significant because the couple’s serendipitous reunion here – which comes after break-ups and as they’re starting to heal – leads to them hanging out as friends.

Cut to the Metropolitan Museum of Art, located eight blocks away, just inside Central Park. It’s the largest art museum in the country, packed with classical and historical works from the around the world. But the only section that’s applicable to this tour is the Sackler Wing, where Harry and Sally meander around the Temple of Dendur, which was saved from being drowned by the Aswan Dam. It’s here that Harry gave the famous line: “Waiter, there is too much pepper on my paprikash,” in a smile-inducing Eastern European accent.

From here, you can walk to Central Park’s Loeb Boathouse, where Sally and her friends have a lakeside lunch in which Marie whips out an ancient, pre-mobile phone, paper-based device called a Rolodex. Later in the film, Harry and Jess powerwalk (a trend that also went the way of the Rolodex) by the nearby Bethesda Fountain. Stroll by as you cross the park west toward the Museum of Natural History, which has a cameo in the film.

Central Park is a romantic place to end the tour, but Harry Met Sally die-hards will want to schlep on, even if the return on investment starts to dwindle. The beautiful (and privately owned, so don’t loiter) Brownstown apartment just off the park at 32 West 89th Street is where Jess and Marie lived. It’s also home to two of the funniest bits in the film: the “baby fishmouth” Pictionary scene and the cautionary divorce tale illustrated by the “stupid Roy Rogers wagon wheel coffee table”.

Another easy stroll away, on West 96th, is the Plant Shed, where Harry and Sally adorably buy a Christmas tree together – though it’s mainly the church next door you see in the film. A year later Sally returns, pathetic in her inability to manage carrying her tree home alone. The Plant Shed sells trees every December if you want to recreate either scene.

Dinner awaits just around the corner at the high-end French bistro Café Luxembourg, where Jess and Marie try to fix up Harry and Sally with each other, but end up together themselves. “Restaurants are to people in the ‘80s what theatres were to people in the ‘60s,” writes Jess, as quoted by Marie. And Luxembourg is  still popular 25 years later.

“…on the side”
If you know the name of Harry’s ex-girlfriend who was also Sally’s college roommate, or if you can answer the question: “When are you going to turn 40?” with the movie’s punchline, then you should probably make pilgrimages to the outer borough and New Jersey sites of Coney Island, where Harry and Jess practice in batting cages that no longer exist; John F Kennedy International Airport, where Harry met Sally for the second time; and MetLife Stadium – its predecessor, Giants Stadium (torn down in 2010), is where Harry’s soliloquy of soon-to-be divorced woe is punctuated by the wave. Landmarks come and go, but love is here to stay.