Feelings are like water slides or pet snakes. When they get big enough, they get kind of scary. But if you recently developed feelings for someone you’ve been hooking up with, don’t just panic, fake your death, and start a new life on a fishing boat in Nova Scotia. Plan a dinner at one of these places instead. They’re all kind of romantic, but they’re also casual enough that you won’t feel like you’re committing to a lifetime of quiet walks, half-finished crosswords, and shared toiletries with this person you only just started to like.
Oh god, do you like this person? Are the two of you going to spend the rest of your lives going to Halloween parties in couples’ costumes until you both decide that you’d rather stay home and go to bed early so you can wake up and catch an early workout class? Is that what your life is now? Absolutely. And we suggest you lean into it, and go to Cervo’s on the Lower East Side. Sit at the bar, drink some good wine, and share a few seafood small plates with this person who says charming things like, “Wine makes me sleepy.” Come here often enough, and you can even start telling other couples that this is “your spot.”
Remember, this is a new and mostly undefined relationship, so you don’t want to come on too strong and suggest a dinner at a place where it seems like you might propose or suggest a joint checking account. Instead, go to Red Hook Tavern, a dark, old-school restaurant in Red Hook decorated with candles, wine bottles, and some classy floral wallpaper. Put your name in for a few seats at the bar, split a burger and some chicken liver mousse, and try to figure out if you actually like this person or if you’re just lonely and confused. Whatever you decide, order gelato for dessert.
One day, you might go to Italy with this person. Maybe you’ll even wear matching striped shirts, rent a vintage Fiat, and cruise down the coast while laughing at nothing in particular. Before you get to this point, have a casual meal at Vini E Fritti. They only serve small plates at this Nomad wine bar, so you can either just pick at a few pillows of fried dough with prosciutto on top, or you can eat a full meal and order some pork ribs, potato pancakes, and fried artichokes (all of which are delicious).
Chez Ma Tante is impressive in an understated sort of way, and so are you. Or maybe you aren’t, but you’re trying to be. Either way, book a table at this neighborhood spot in Greenpoint, order a caesar salad and some pork shoulder, and smile in a non-creepy way while your date tries to figure out if you’d be a suitable long-term romantic partner. It isn’t too hard to get a table here, despite the fact that the food is excellent, and the space is clean, minimalist, and grown-up without feeling stuffy.
Maybe the first time you two ate together, your meal consisted of a couple of slices, and neither of you were particularly sober. Now that you’ve grown, changed, and developed emotions that are equal parts confusing and exciting, it’s time to sit in a nice room and use silverware to eat a plate of food. If you’re on the UWS, we suggest Marlow Bistro. It’s a Mediterranean spot where you can eat some solid pastas and thin-crust pizzas in a charming space with tiled floors and lots of plants.
You have feelings now, so you walk around listening to Trey Songz and Sam Smith, and you cry whenever you watch the opening sequence of Up. But you still need to play it cool, so arrange a casual dinner at Milkflower in Astoria. If you aren’t sure how to propose this, try something like, “Hey, would you like to eat pizza with me?” That sounds pretty casual. Also, the Neapolitan pies at Milkflower are great, there are a bunch of other things on the menu like octopus and meatballs, and you probably won’t be the only date here.
Fancy Nancy is a starter restaurant. It’s where you go with someone when you aren’t entirely sure if you want to meet their family or go hiking with them once a year for the next several decades, and it’s the kind of place where you can hang out for either 30 minutes or several hours. This Bed-Stuy spot also has a solid burger, a neon color scheme, and little TV that you can watch in case your feelings take a u-turn and you’d rather not talk to your date.
If you’re afraid of rejection, pretend you want to go on a dinner date ironically. Say that you think it would be funny if you drank wine, held hands, and ate French food together. Arrange a dinner at Le French Diner. It’s a tiny spot on the LES you’ve probably walked past, and it’s extremely casual, somewhat cramped, and just the right amount of romantic. Order the steak with a side of cheesy potatoes, and be sure to ask if your date would like some or all of the cheesy potatoes.
You don’t have to eat a full dinner at Maison Yaki in Prospect Heights. Most of the menu at this French-Japanese spot (from the people behind Olmsted) consists of individual skewers. So if you aren’t quite ready to commit to a long meal during which you might accidentally sneeze on your date’s face or express an incorrect opinion on Maggie Rogers, come here, and have a few drinks and snacks. We especially like the lobster meatball and duck l’orange skewers, and we suggest you make a reservation. Because this place is cool, and cool places get busy.
Yes, Have & Meyer could technically work for a first date - but we always end up spending more money than we expect to here. So save this place for when you know for a fact that you won’t regret spending $70 on four glasses of wine with your date. This tiny Williamsburg wine bar feels like a study in an eccentric millionaire’s 19th-century mansion, it’s packed with wine bottles, and there are over 100 wines by the glass. There’s also some perfectly fine pasta, as well as a bunch of meat and cheese, which is usually what we stick to when we come here.
Perhaps you’re a coward, and you aren’t ready to sit across a table from your date and confront your emotions by making solid eye contact and asking thoughtful questions. That’s fair. Just go sit at the bar at Archer & Goat, a casual restaurant/bar in the bottom of a townhouse in Harlem. Eat some arepas or a burger, and have a few cocktails while you stare straight ahead and think about whether you’re ready to settle down, date this person, and stop sending suggestive Shrek memes to all the other people in your personal contacts.
Camillio is a notch above your average neighborhood Italian spot, and bringing someone here sends the message that you like them and not just in a physical sort of way (but also probably in physical sort of way). With its brick walls and marble bar, it looks kind of like a sleek Italian farmhouse, and the pastas and Roman-style pizzas are great. You’ll probably also see a few families here, so if you’d like a preview of what your future might hold, you can squint and pretend you’re one of them.