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Swing dancing and a speakeasy
Get things jumping Jon Favreau--style with a private swing dancing lesson from one of the pros at Dance Manhattan Studios (39 W 19th St between Fifth and Sixth Aves, fifth fl; 212-807-0802, dance-manhattan.com; $80 per couple). Over the course of an hour, you'll learn the fast-paced footwork of the Lindy Hop, which had its beginnings in 1930s Harlem (represent!). Then quickstep over to modern-day speakeasy Raines Law Room (48 W 17th between Fifth and Sixth Aves, no phone) to sip neoclassic cocktails like the gin-and-cucumber-based Archangel ($13). Snag one of the curtained booths in the back and you might just get to second base—over the shirt, of course.
Burger and a movie
What could be more classic than dinner and a movie? Try an all-American burger paired with a black-and-white film. Begin your night at the venerable Minetta Tavern (113 MacDougal St between Bleecker and W 3rd Sts; 212-475-3850, minettatavernny.com), where you can sit at the handsome wooden bar (which dates back to 1937) and split the sumptuous Black Label Burger ($26) and a side of pommes frites ($9). Then catch a screening of Bride of Frankenstein or The Invisible Man at Film Forum (209 W Houston St between Varick St and Sixth Ave; 212-627-2035, filmforum.org; $12), which is hosting a weeklong homage to British director James Whale from Friday 4 through December 10. Just don't let us catch you necking in the back of the theater. Crazy kids.
A jazzy blast from the past
It always looks and feels like the 1920s in Cobble Hill's elegant Clover Club (210 Smith St between Baltic and Butler Sts; 718-855-7939, cloverclubny.com)—witness the wood-paneled walls and retro cocktails like the Pink Lady (gin, lemon, house-made grenadine and egg white, $11). On Wednesdays from 9 to 11:30pm it sounds like the 1920s, too, thanks to the jazz standards and ballads performed by Michael Arenella & His Dreamland Orchestra. After swaying to the music, slip over to the Victorian dining room at Prime Meats (465 Court St at Luquer St, Carroll Gardens, Brooklyn; 718-254-0327, frankspm.com) and let the mustachioed waitstaff serve you juicy New York strip steaks ($20 each). Just make sure to be home by midnight.
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