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.
Most steakhouses are cool in an old-timey kind of way - in other words, not exactly trendy. And while Holy Ground has a lot of familiar features (like red leather booths, low ceilings, and great martinis), it also has things you definitely won’t find at spots in Midtown or FiDi. Most notably, slow-smoked meats. So instead of a porterhouse, get a whole rack of ribs served tableside - the meat is charred and smoky, and falls right off the bone when you pick it up.
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.
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.
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 Yakitori 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).
Just east of Tompkins Square Park, there’s a tapas place called Donostia. It’s small and easy to miss, but it has an enormous menu of pintxos and other Spanish dishes, like salt cod and razor clams on little pieces of bread. It can get a little pricey depending on how much you order, but it makes it easy to try a bunch of things, and there’s a great selection of sherry that you can pretend to know a lot about. The space is long and dimly lit, so it works especially well for a date.
If you’re meeting in East Williamsburg, you have some options everyone already knows about, like Roberta’s. Try this less-well-known spot instead. It serves high-quality American/Mediterranean food like mussels, ribs, and duck confit, and has a nice space you’ll want to hang out in for a while.
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 here.
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.
There’s an advertising team in town from Paris, and you need to take them out in Midtown. Go to The Polynesian, a tiki-themed bar in the Pod Hotel near Times Square from the people behind Carbone and The Grill. Sit at a booth in the dining room for some really good bar food, then move to the wraparound terrace overlooking Midtown for a round of rum cocktails that come out on fire in mugs shaped like skulls.