Best date spots: Flatiron, Gramercy and Murray Hill

This snug restaurant features three dining areas; we’re partial to the main one, outfitted with a romantic chandelier and a bright fireplace that’s used to warm focacce, ciabatte and pizzas before they’re served. Chef Shea Gallante, formerly of Cru, oversees the menu, plus a rotating selection of daily specials.

This massive food and drink complex, from Joe and Lidia Bastianich is the largest Italian market in the world. The New York flagship takes inspiration from Oscar Farinetti's Eataly Torino Italy, which opened back in 2007, with a sprawling 48,000-square-feet maze of awe-inspiring stands filled with hard-to-find, high-quality produce, cafés and restaurants. It's a chance for New Yorkers to educate their tastebuds on the nuances of Italy's 20 regions.

Explore this institution’s collection of titillating photographs, vibrators, films, sculptures and all manner of erotic and outlandish ephemera while exchanging coy, subtextual glances. If you’re heading back to one of your apartments afterward, stop by the institution’s souvenir shop and pick up a set of Sex! Dice to liven up the rest of the evening.

Drum up enough fodder for several more dates of inside jokes by enjoying a night of comedy at the PIT. Grab a beer from the bar and settle in at the proscenium or black-box theater to watch sketch and improv groups do their thing. The shows are all either cheap or free—and reliably funny—so you pretty much can’t lose.