An old Hollywood Valentine's Day

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

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  • Photograph: Courtesy of onthesetofnewyork.com

    How to Marry a Millionaire

  • Adam's Rib

  • Photograph: Courtesy of onthesetofnewyork.com

    The Lost Weekend

Photograph: Courtesy of onthesetofnewyork.com

How to Marry a Millionaire

Toast the town like a starlet

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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Flatiron Building

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.

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Claim some Hepburn-Tracy chemistry

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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Go boozing like it's 1945

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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