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We can already tell you with full confidence—like, statistically significant confidence—that this date night plan has a 100% long-term success rate. How can we be so sure? Well, let’s just say our founder, and the brains and beauty behind your daily plans for lovin’, had her first date with her man with this one-two punch of ‘za and Zinc Bar.

Pizza keeps this date night casual and of the people, but at OTTO enoteca pizzeria, our favorite cheesy carb gets transformed with a little wine bar action that significantly ups this celeb-chef restaurant’s game. Aside from delicious, mouth-watering, often truffle-finished pizza, there’s also an extensive and fresh antipasti menu, a knowledgeable sommelier to help you pair your reds with your red sauces, and ambiance for days. Sweeten the date with a gelato creation or an order of butterscotch budino before heading to the second half of date night.

Formerly Club Cinderella in its heyday, the original forties nightclub that now houses Zinc Bar is where Thelonious Monk, Billie Holiday, and Frank Sinatra used to cut loose and perform for the crowds. These days, the space still retains much of its sexy, sultry gin-joint feel thanks to heavy velvet curtains, Art-Deco inspired decor, and soft candlelight. Settle back, enjoy your cocktails, and let the live music and ambiance set the scene for the rest of the evening.