An old Hollywood Valentine's Day

These classic film locations in New York City bring on the romance.

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  • An Affair to Remember

  • The Seven Year Itch

  • Photograph: Courtesy of onthesetofnewyork.com

    On the Town

  • Photograph: Courtesy of onthesetofnewyork.com

    Breakfast at Tiffany's

An Affair to Remember

New York is the romance capital of the world—at least on this side of the Atlantic—but our shining metropolis didn’t earn this title all on its own. Thanks in no small part to a number of classic Hollywood films, the city enjoys a reputation as a place of elegant avenues, majestic skyscrapers and parks with horse-drawn carriages. Viewed in stately black and white (or newly introduced Technicolor), even the George Washington Bridge can look enchanting. This Valentine’s Day, tap into old-school glamour by visiting classic film locations. Audrey Hepburn and Marilyn Monroe not included—but romance guaranteed.


RECOMMENDED: Valentine's Day ideas for New Yorkers


An Affair to Remember

Meet your significant other at the top of the Empire State Building

Many people might credit Sleepless in Seattle for establishing the Empire State (350 Fifth Ave at 33rd St; 212-736-3100, esbnyc.com) as a meeting spot for romantic liaisons, but the reference actually goes back to 1957’s An Affair to Remember (or perhaps even further, considering that An Affair was a remake of a 1939 film). Regardless, Cary Grant and Deborah Kerr own the weepy drama, which depicts the two lovebirds getting acquainted on a transatlantic voyage and vowing to meet at the iconic building six months later. Alas, Kerr’s Terry is struck by a car and crippled on her way to meeting her lover, leaving Grant’s Nickie alone on the observation deck. An awkward run-in after the missed connection produced this classic romantic movie line: “And all I could say was, ‘hello.’ ” Twists of fate aside, the view is hard to beat: “The Empire State Building is the closest thing to heaven in this city,” says Terry.

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The Seven Year Itch

Stand over the famous Marilyn Monroe subway grate

While everyone knows the image, not everyone knows the film it comes from. That would be 1955’s The Seven Year Itch, which cast the sprightly bombshell alongside an everyman (Tom Ewell) looking for some excitement when his wife and kid leave town. Left to his own devices, Ewell’s Richard contemplates an affair with the model renting an upstairs apartment, taking her out to the cinema on a particularly breezy summer evening. The windblown skirt speaks for itself, as does Monroe’s casting: Her character is simply known as the Girl—a classic-film sex object if there ever was one. Arrange an illicit rendezvous while wearing your own billowy white dress at the subway grate on the corner of Lexington Avenue and 52nd Street, where the scene was filmed.

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On the Town

Reenact Sinatra and Kelly’s tour of New York

In the 1949 film On the Town, Frank Sinatra, Gene Kelly and Jules Munshin star as three love-starved sailors whose 24-hour leave in the big city sends them on the hunt for some pretty dames—in particular, an actress Kelly’s character spots in a picture. In record time, the wayward visitors check in at more iconic tourist spots than a sixth-grade Girl Scout troop, including the Statue of Liberty, the Brooklyn Bridge and the Washington Square Park arch. Eventually, they find the actress (Vera-Ellen), as well as love interests for the other two, and share farewell kisses with their lady friends on the pier. We suggest that you choose the sunken courtyard at 30 Rockefeller Plaza (49th St between Fifth and Sixth Aves): It’s where the city’s original anthem (predating even Sinatra’s own song of the same name), “New York, New York,” was first performed. Sorry, Jay-Z.

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Breakfast at Tiffany's

Capture some of Audrey Hepburn’s elegance

The flighty Holly Golightly (Audrey Hepburn) is one of the most memorable characters in cinema—not to mention a model of classic fashion. Hepburn immortalized the role in 1961’s Breakfast at Tiffany’s, which shows the eccentric Holly living in an Upper East Side apartment (169 E 71st St between Lexington and Third Aves). Visit the abode for a dose of romanticized film history, or, you know, just go to Tiffany’s (727 Fifth Ave at 57th St; 212-755-8000, tiffany.com), where Holly and Paul get the Cracker Jack ring engraved, of course.

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