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A date plan

A Playful Nolita Evening

Date · Nolita · Fun & Playful

Start with wine and intimate conversation at a cozy wine bar, play some nostalgic games for a fun break, and finish with decadent chocolate treats that'll make you both smile.

01Drinks & Appetizers

Nolita · $$ · Wine bar

Brick Wine Bar hits the sweet spot between laid-back and romantic—exposed brick, dim lighting, and a thoughtfully curated wine list that won't intimidate. Grab a glass of something interesting and some cheese; the vibe is intimate without trying too hard.

21 Clinton St, New York, NY 10002

~10 min walk (0.5 mi). From Brick to Game of 1000 Boxes, you're heading west toward Bowery—the energy shifts from wine-bar intimate to playful and lively. It's a fun tonal shift that keeps the night from getting too serious.

02Activity

Nolita · Amusement center · Event venue

Game of 1000 Boxes is exactly the kind of playful detour that breaks the ice and keeps things fun. Think vintage arcade games, board games, and retro nostalgia in a pumped-up lounge setting—perfect for some friendly competition and a few laughs together.

302 Bowery, New York, NY 10012

~6 min walk (0.3 mi). After some competitive fun, make your way south to Chocolate DIP on Orchard Street—you'll drift slightly east into the heart of Nolita proper, where the charm is undeniable and dessert calls.

03Dessert

Nolita · $ · Chocolate shop · Chocolate cafe

Chocolate DIP is the perfect sweet finale—a dreamy chocolate café where you can indulge in crepes, truffles, and over-the-top chocolate creations. It's rich, a little bit decadent, and impossible not to smile about.

177 Orchard St, New York, NY 10002

Curated by NYC Date Ideas