An Old Hollywood Valentine’s Day

Arts & Entertainment

by Eva Medoff, Time Out New York contributor, 02/01/2012

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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.

Meet your significant other at the top of the Empire State Building
Many people might credit Sleepless in Seattle for establishing the Empire State Building (350 Fifth Ave at 33rd St; 212-736-3100, 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.

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.

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,, where Holly and Paul get the Cracker Jack ring engraved, of course.

Visit the Flatiron Building like Jimmy Stewart
For a romantic moment south of 40th Street, look no further than Madison Square Park. It’s there, says Maynard, that Jimmy Stewart romanced Kim Novak, at the top of the Flatiron Building (175 Fifth Ave between 22nd and 23rd Sts), in 1958’s Bell Book and Candle. Or rather, she romanced him: Novak plays a Greenwich Village witch who casts a love spell on her unsuspecting neighbor. As the two gaze at the park below, Stewart’s character muses, “There’s a timelessness about this. I feel spellbound.” Take a stroll with your sweetheart and get enraptured by Manhattan’s classic scenery as well.

Go boozing like it’s 1945
Stop at P.J. Clarke’s (915 Third Ave at 55th St; 212-317-1616,, where down-on-his-luck writer Don Birnam (Ray Milland) drinks his troubles away in The Lost Weekend. Of course, the love of a good woman is all that’s needed to solve his problems, and he finds it in Jane Wyman’s Helen. Bring your own Helen or Don and enjoy Valentine’s Day in this drinking hole of yesteryear, where stained-glass windows, red-checked tablecloths and walls cluttered with black-and-white photos cast a romantic glow.

related venues/(4)

  1. 1
    Empire State Building Observatory
    350 Fifth Ave.
    Manhattan – Garment District
    NY 10118
  2. 2
    Tiffany & Co.
    727 Fifth Ave.
    Multiple Locations
    NY 10022
  3. 3
    Flatiron Building
    175 5th Ave
    Manhattan – Flatiron District
  1. 4
    P.J. Clarke’s
    915 Third Ave
    Manhattan – Midtown East
    NY 10022

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