There’s more to life than being cool. But when you need to plan a dinner with someone you know or strongly suspect to be cooler than you, that’s easy to forget. So here’s a list of restaurants that will help convince this person you’re actually the cool one. It has some places that aren’t too well-known, plus others that are objectively impressive but not impossible to get into. Eat dinner at one of them, then stop worrying what this person thinks - at least until the next time you have dinner together.
At Mo’s Original in Prospect Lefferts Gardens, you can eat ribs, ramen, and some predictably delicious tater tots. The food is a unique mix of Caribbean, Japanese, and American, and it’s perfect for when you need to eat with someone who has better taste in music and/or has read more books than you. The space is plain, white, and filled with potted plants (which is currently the default setting for new NYC restaurants), and nothing on the menu costs more than $20.
The name Win Son Bakery is misleading. Yes, it’s a bakery, and it’s from the people behind Win Son (directly across the street in East Williamsburg), but there’s more than just baked goods here. Fried chicken, for example, and a burger on a squishy milk bun with what seems like half a cup of a creamy secret sauce we’d gladly eat with a spoon if only the world were filled with more tolerant people who choose to make meals out of condiments. This place is counter-service, but there’s a full bar, and the whole operation is just as impressive as most non-counter-service spots.
Red Hook Tavern has brick walls, floral wallpaper, and a great selection of natural wine. In other words, it’s a trendy restaurant in Brooklyn, and you probably know several people who’ve been meaning to eat here. It’s crowded pretty much every night, but there’s a long bar reserved for walk-ins, so stop by with someone you’re trying to impress, put your name in, then come back and eat a romaine wedge salad and buttery burger draped in cheese.
A dinner at Turk’s Inn is an event. There’s just something about the abundance of retro decor that makes this place feel like a brief trip to an alternate universe in which overdecorating is not and will never be a thing. The walls are covered in plates and portraits, the U-shaped bar is surrounded with gold tassels and taxidermy, and all the way in the back, you’ll see a majestic cat painting watching over everything. Also, the Mediterranean food is pretty solid (get some fried halloumi and a plate of crudites), and you can stop by the casual rooftop bar for a drink after dinner.
Momofuku Ko is an excellent restaurant. It also costs $255 per person. But there’s a place where you can eat similarly great food for a fraction of the price. It’s called Ko Bar, and it’s the small, semi-separate space at the entrance to Momofuku Ko. The menu is a la carte and changes daily, but you can expect things like a flaky duck pot pie and some cold fried chicken soaked in a sweet glaze. The best part is, you don’t need a reservation to eat here (Ko Bar is walk-in only), and most people don’t seem to realize this place exists.
Bring someone to Bernie’s, and this person will probably start telling people it’s their new favorite restaurant. They’ll say things like “Have you been to Bernie’s?” and, “I miss the mozzarella sticks at Bernie’s,” and you’ll just sit there, knowing that you introduced this cool-yet-irritating person to Bernie’s. Think of this Greenpoint spot as a darker, smaller, and better version of TGI Friday’s. The tables are covered in red-checkered tablecloths, and they serve things like buffalo wings, shrimp cocktails, and a fast-food style double-patty burger that’s worth a trip all by itself.
Maybe you’re grabbing food with someone who’s in the market for a new denim jacket or a jumpsuit. Yes, you could make two stops - or you could go to Bangklyn in East Harlem, where there’s a small collection of vintage clothing for sale. This place is counter-service and about as casual as a coffee shop (because it’s one of those as well), and the owner might tell you a story about Alexander Wang while you eat some khao mun gai or tamarind coconut noodles tossed with an ample amount of crab.
On top of being worried about the normal date stuff, like avoiding awkward silences and making sure you don’t have arugula in your teeth, you also want to pick a spot that says, “I’m clearly into cool sh*t.” Try this 20-seat East Village wine bar. Get some really good small plates from the constantly-changing menu, then ask the bartender to tell you about some of the 250 natural wines they serve. That should give you a few seconds to check the food-in-teeth status with your phone camera, too.
Celebrities hung out at Florent and The Odeon in the ’80s, artists and tourists hung out at Balthazar in the ’90s, and now people who like natural wine, excellent French-ish food, and loud, crowded scenes go to Frenchette. Provided they can get in. Make a reservation here well in advance, and if you want to look as cool as possible, order the lobster. Everyone around you will be jealous.
Your friend posts pictures from European beaches and luxury resorts in the middle of the desert, and somehow she’s already been to all the more upscale places you suggest. So go another route, and meet at this BYO pizza spot in Carroll Gardens. You might have to get there two hours before her to put your name down, but she doesn’t need to know about that, and this will be some of the best pizza either of you has ever had.
There are a lot of restaurants on the lower part of the Lower East Side, and they tend to be filled with people who keep track of things like clothing trends and pop culture. So if you want to convince someone you know about that stuff, take them to Cervo’s. It’s a Portuguese-inspired place from the people behind Hart’s, and they have some great seafood small plates as well as a very good lamb burger. There’s also a long bar, which is where you should drink wine and eat clams while talking about whatever shows everyone is supposed to be watching.
This Japanese spot on the LES is the size of a studio apartment, but serves dishes ranging from oden (small bowls of dashi broth with ingredients like daikon or fried octopus) to Japanese spaghetti topped with a ton of uni. Sit at the counter drinking natural wine while you watch the chef prepare your dinner, and wait for your popular-kid cousin to suggest that you pick the place next time, too.
Take 31 is a Korean restaurant on 31st Street from the same people behind Her Name is Han and Nonono - and if you know what to order here, you’ll easily impress whoever you’re having dinner with. First off, get a stew for the table. It comes in a big metal pan with a flame underneath, and it’ll be enough for two people. Next, get a jar of makgeolli, a Korean rice wine they blend into slushy form with things like peach and banana. At this point, you should be doing just fine, although getting a seafood pancake too isn’t a bad idea. Just be sure to get here early, because it fills up fast (they don’t take reservations).
If you’re pretty sure your friend is more interested in showing off a new haircut than eating something good - but you’re personally more interested in food - go to Dirty French. Your friend can enjoy the experience of eating in a room full of expensively dressed people, while you enjoy some really good variations on traditional French dishes, along with drinks from the long wine list.
Simon & The Whale is the main restaurant at the Freehand Hotel, but there’s another one from the same people on the second floor. It’s called Studio, it’s open all day, and it feels kind of like a clubhouse for people who work for fashion magazines (with a bar, a bunch of potted plants, and some booths in the middle draped with fur blankets). There’s a good chance you’ll see someone you recognize from social media eating a lamb burger or some grains with avocado and tahini, if that’s not the person you came with in the first place.
The first time you go to Le French Diner, you’ll wonder how it took you so long to find out about this place. It’s a tiny French restaurant on the Lower East Side that looks like a casual wine bar - and while you can definitely get wine here, you mostly come for the food. Try the steak that comes with a square of cheesy potatoes, or the octopus or the escargots. Or all three. You can’t really go wrong.
If you’re meeting in East Williamsburg, you have some options everyone already knows about, like Roberta’s or Win Son. Try this lesser-known spot instead. It serves high-quality American/Mediterranean food like mussels, ribs, and duck confit in a nice space you’ll want to hang out in for a while.