An old Hollywood Valentine's Day

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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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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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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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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The triple threat of Lauren Bacall, Marilyn Monroe and Betty Grable commands the screen in the 1953 film How to Marry a Millionaire, a tale of three lasses who rent an upscale apartment in the hopes of entrapping rich husbands. The movie features shots of both the George Washington Bridge and their Upper East Side digs (36 Sutton Pl between 58th and 59th Sts), where Bacall's character declares, "The first rule is, gentlemen callers have got to wear a necktie," a sartorial tip dudes would be well served to remember. If the gold-digging theme seems a bit anti–Valentine's Day, don't worry: Love wins out in the end of the movie.

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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.

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Adam's Ribis known not only as a seminal romantic comedy, but also as an early feminist film. The year was 1949, the players were Katharine Hepburn and Spencer Tracy, and the plot was classic him-against-her. Unlike most relationships, this couple's battle plays out in the courtroom, as Hepburn's defense attorney squares off against Tracy's prosecutor in a case of spousal abuse. Visit the Criminal Courts Building (100 Centre St between Leonard and White Sts) to see where it all went down. Unconventional? Yes. But worth it—the real-life couple had one of the most famous love affairs in Hollywood history.

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Stop at P.J. Clarke's (915 Third Ave at 55th St; 212-317-1616, pjclarkes.com), 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.

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