Date Night: Chelsea

Dining and drinks advice for every date

Love is hard enough—so no matter how noncommittal or committed you are, you should have a game plan for your next big date.

Look no further than ever-evolving Chelsea, which is packed with places for every stage of courtship, whether you've just swiped right and have a drinks date lined up or you're ready to meet the 'rents.

First Date

"Never. Do. Dinner. On. The. First. Date." Such is the emphatic advice delivered by a wise older divorced man we know—and we tend to agree. Long dinners can feel like endless job interviews. But keeping it loose doesn't mean you have to be cheap: Get to know each other over fancy cocktails at speakeasy-esque Bathtub Gin. Enter through a door marked with a red light at the back of the Stone Street Coffee Company shop, slip into a tufted leather booth and order a classic Vesper or Negroni Bianco ($15). First impressions count, so don't have so many you pass out in the copper bathtub.

Day Date

So the thought of spending a few hours with this person—in broad daylight, no less—doesn't freak you out. Congratulations! Swing by the new Manhattan location of fancy food and cheese shop, Stinky Bklyn, and pack a picnic for the Highline: a few nubs of runny Tome d'Aquitaine washed-rind goat cheese ($7.50 per quarter pound) or a block of Plymouth aged cheddar ($11); a package of La Quercia's speck Americano ($11); a baguette from Sullivan Street Bakery ($3.75); some fresh raspberries ($6 per pint). Grab a bottle next door at Back Label Wine Merchants (also owned by Stinky Bklyn) or keep things casual with a few cans of Stillwater Brewery's Classique farmhouse ale ($2.50 each). Cheers, eat cheese, repeat.

DTR Dinner

You want to take things to the next level. Or you don't. Either way, you're eventually going to have the inevitable semi-awkward, sorta sweet "Define the Relationship" (DTR) convo. You may as well do it in the grownup-but-fun and always solid French bistro Montmartre: oysters on the half shell ($16 for a half dozen), chicken liver mousse ($6), a killer burger topped with dreamy house-made béarnaise cheese on toasted pain au levain ($19). Request a table in the back garden where, after you've declared your love, you can get handsy over pommes frites with aioli and brown butter sabayon ($9).

Meet the Parents

Is this a date? Well, whatever it is, it's a stressful situation calling for just the right reservation and gin cocktails. Play it smart with a Sunday night at Barchetta. Parents will approve of the reasonable sound-level and comfortable leather banquettes. Break the ice over strong drinks, like the Whisperer ($15): gin, cocchi and averna. And nothing soothes family drama like distracting everyone with lots of good pasta: buttery, breadcrumb-topped bavette noodles with crab and onion flowers ($23) or fettuccine studded with chunks of lobster meat, English peas and sorrel ($28).

The Post-It's-Not-You-It's-Me Meal

Hey, things don't always work out. Date night for one! Eat your feelings—and tons of carne asada tacos on handmade corn tortillas ($3.50)—at Los Tacos No. 1 in Chelsea Market. There are no tables so you avoid the one-top guac of shame. Order extra chopped onions—because who cares? And you can always blame the tears on the chile de arbol you just bit into.