… Sign up for a guerrilla class
Main Event
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Learn how to doodle, resolve conflicts, or look better dancing at LeeAnn Renninger’s experimental school, LifeLabs New York (32 Prince St., at Mott St.; lifelabsnewyork.com). Classes are affordable ($35 to $135), and teach skills you never knew you needed (to wit: this Tuesday’s sold-out workshop on coolness).
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Wind Down
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Continue bucking convention by dining nearby at the Kickstarter-funded pop-up restaurant What Happens When (25 Cleveland Pl., nr. Kenmare St.; 212-925-8310).
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… Bowl while dancing, or vice versa
Main Event
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Every Thursday night, ?uestlove packs all sixteen lanes and the dance floor at Brooklyn Bowl (61 Wythe Ave., nr. N. 11th St., Williamsburg; 718-963-3369; 11 p.m., $5 advance, $8 day of) for his Bowl Train parties. Soul Train videos play on the big screen while the Roots drummer spins rare funk, soul, R&B, hip-hop, and eighties cuts.
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Wind Down
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Keep the competitive juices flowing at the arcade bar The Whiskey Brooklyn (44 Berry St., at N. 11th St., Williamsburg; 718-387-8444).
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… Bust a gut laughing
Main Event
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Catch Wyatt Cenac, Billy Eichner, Look at This Fucking Hipster’s Joe Mande, and other rising comedic talents at Splurge!, a free showcase on the second Friday of every month at Happy Ending (302 Broome St., nr. Forsyth St.; 212-334-9676).
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Wind Down
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Land some hipster jokes of your own at gastropub-of-the-moment The Fat Radish (17 Orchard St., nr. Canal St.; 212-300-4053).
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… Shop for old stuff
Main Event
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Browse for used books, records, handmade jewelry, vintage clothing, and kitschy bric-a-brac at Artists & Fleas, the recently relocated pillar of Williamsburg’s secondhand scene (70 N. 7th St., nr. Wythe Ave.; weekends noon to 8 p.m.).
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Wind Down
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Tuck into some Cajun-Creole delights from Tchoup Shop BBQ every Sunday afternoon at d.b.a. (113 N. 7th St., nr. Berry St., Williamsburg; 347-223-2710; starts April 17).
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… Smoke something legal
Main Event
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Three-month-old hookah bar Hash55 (47 W. 55th St., nr. Sixth Ave.; 212-957-1899) supplies $30 bowls of flavored tobacco (apple, strawberry, orange, etc.) along with Middle Eastern–leaning cocktails, like the $11 Sand Storm (dark rum with cinnamon, burnt honey, and apple).
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Wind Down
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Trek from Arabia to Asia for bibimbap burgers and yuzu cream puffs at Angelo Sosa’s new Social Eatz (232 E. 53rd St., nr. Second Ave.; 212-207-3339; opens 3/10).
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… Watch tassels twirl
Main Event
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The French bistro–cum–burlesque house Affaire Restaurant & Lounge (50 Ave. B, nr. 4th St.; 212-375-0665) offers two dinner-and-a-show seatings (from $30) on Wednesday nights for up to fifteen couples in its bordello-ish subterranean Candle Room.
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Wind Down
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Sidle up to the copper bar for some dessert wine and cheese at nearby Austrian tavern Edi & The Wolf (102 Ave. C, nr. 7th St.; 212-598-1040).
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… Catch an art-house flick
Main Event
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So this is where the young film nerds are hanging out now. Williamsburg’s one-screen Spectacle Theater (124 S. 3rd St., nr. Bedford Ave.) shows rare films, cult classics, bizarro sci-fi, and silent movies accompanied by live music—all for $5.
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Wind Down
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Slurp oysters and clink absinthe glasses at Maison Premiere (298 Bedford Ave., nr. Grand St., Williamsburg; 347-335-0446).
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… Sample jazz and pork chops
Main Event
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Come for the rib-sticking supper-club grub at The Astor Room (34-12 36th St., nr. 35th Ave., Astoria; 718-255-1947). Stay for the retro cocktails (named after the stars, like Rudolph Valentino, who used to drink here) and the live jazz piano.
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Wind Down
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Cut the rug to Euro-pop hits at Croatian soccer lounge–dance hall Veslo (32-11 Broadway, nr. 33rd St., Astoria; 718-728-0549).
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What If We …
Unconventional date-night ideas, in two acts.
From the 2011 Best of New York issue of New York Magazine