Where to Recreate Classic Romantic Comedy Scenes in NYC

Gillian Osswald

New York City has played a starring role in countless romantic comedies, which means a visit to the five boroughs is a great chance for rom-com fans to bring their favorite movie moments to life. We’ve rounded up some of the most memorable reunions, dramatic confessions and other pivotal romantic comedy scenes that took place at real NYC locations; grab your camera phone and a fellow fan or two and follow our guide to recreate them yourself.

Moonstruck (1987)
The Metropolitan Opera plays no small role in the love story of Ronny (Nicolas Cage) and Loretta (Cher). Meet at the Met to revisit the site where the two confirm their connection, exchanging meaningful glances while watching the opera singers on stage confess their love for each other. You don’t necessarily need to attend a performance of Puccini’s La Bohème, but you will want to carve out some time to dramatically stare while circling the Lincoln Center fountain.

Working Girl (1988)
Working girl Tess (Melanie Griffith) commutes to her Wall Street office every day on the Staten Island Ferry. You can channel her big-pitch energy by strutting into the Alexander Hamilton US Custom House in Lower Manhattan. The building, which houses the National Museum of the American Indian, served as the offices of Trask Industries in the movie. There, Tess presents her idea for Trask to acquire radio stations and scores her dream job.

Illustration by Elizabeth Daggar

When Harry Met Sally (1989)
If you want to have what she’s having (or, more specifically, what Meg Ryan had as Sally in this 1989 movie), order a turkey sandwich and grab a table at Katz’s Deli on the Lower East Side. If turkey’s not your thing, opt for Harry’s more traditional order of pastrami on rye and just fake it.

Sleepless in Seattle (1993)
Follow the fateful footsteps of Sam and Annie (played by Tom Hanks and Meg Ryan) up to the Empire State Building Observatory, the site where Annie, inspired by An Affair to Remember, has proposed she and Sam meet. It’s a thrill to visit this NYC landmark—and see the City from the 86th-floor observation deck—even if you aren’t involved in a serendipitous Valentine’s Day meetup.

You’ve Got Mail (1998)
Reenact another iconic Hanks-and-Ryan reunion in Riverside Park, where Shopgirl and NY152 bring their online relationship into the real world. Their exact rendezvous point is the petite 91st Street Garden (not far from their many other Upper West Side haunts), but any section of this picturesque park is a good place to take a romantic stroll or settle in with a title from your favorite independent bookstore.

Illustration by Elizabeth Daggar

Serendipity (2001)
When you order a Frrrozen Hot Chocolate at Serendipity 3, you join the ranks of the many celebrity guests who’ve enjoyed the restaurant’s signature drink since the 1950s. This includes John Cusack and Kate Beckinsale, who sipped the drink while playing Jonathan and Sara in Serendipity. You can even ask to sit at the table by the fireplace where they filmed the classic scene.

Maid in Manhattan (2002)
This NYC Cinderella story stages its royal ball at the Met Fifth Avenue, where hotel maid Marisa (played by New York native Jennifer Lopez) dances the night away with handsome hotel guest Chris (Ralph Fiennes). Follow their lead and take your own spin through the Temple of Dendur before strolling beside the museum’s charming outdoor fountains. You can also waltz down to the Waldorf Astoria, which posed as the exterior of the movie’s Hotel Beresford.

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How to Lose a Guy in 10 Days (2003)
Andie Anderson (Kate Hudson) and Ben Berry (Matthew McConaughey) cover a lot of New York City territory trying to win the conflicting bets they’ve placed on their relationship (hers to lose him and his to win her over). They ride the Staten Island Ferry, catch a Knicks game at Madison Square Garden and ultimately confess their feelings for each other on the Manhattan Bridge. We don’t advise getting out of a cab on the bridge like Andie, but you might get a comparable rush by glimpsing the Lower Manhattan skyline on your drive (or walk) over the span to Brooklyn.

Hitch (2005)
You may not be able to secure a Jet Ski ride to Ellis Island or an after-hours tour of the place, but you can visit the Ellis Island National Museum of Immigration to mirror the first date Hitch (Will Smith) plans for Sara (Eva Mendes). While you’re there, learn about late 19th- and early 20th-century arrivals to America—excluding, of course, Sara’s murderous great-great-grandfather.

Sex and the City (2008)
This film sequel to the HBO series of the same name subjected us to the not-so-surprising twist in which Mr. Big bails on his wedding to Carrie. To take a page from Carrie’s justifiably dramatic exit, head to her almost wedding venue: the New York Public Library’s main branch. While you could storm down the Astor Hall staircase and directly out the library doors à la Carrie, we recommend at least taking a peek at the stunning Rose Main Reading Room before you leave.

Illustration by Elizabeth Daggar

They Came Together (2014)
Trail Paul Rudd and Amy Poehler (as Joel and Molly) all over NYC in this satirical rom-com. The movie recounts their love story from meet-cute to marriage—and pokes fun at genre classics like You’ve Got Mail along the way. Check out the photogenic view at the site where the two finally come together: the Brooklyn Heights Promenade. While you’re there, maybe sip a nice “cup of Joel.”

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