Unless you sing lead in a band or spend your days writing fantasy novels deep in the woods of Westchester, you probably have someone who tells you what to do. This person is called your “boss” - and you might have to book a table for him or her one day. Sure, you didn’t go to school just so you could make reservations for someone who has more vacation homes than you have pillowcases, but such is life. So here are some upscale spots that are cool enough for your boss, but not impossible to get into (even at the last minute).
No matter what you’re looking for, it’s hard to be upset with The Loyal. The menu is huge, with everything from steak tartare and mushroom carbonara to a kale salad and some roasted chicken with a side of steamed vegetables (that are surprisingly good). It also has a fun, downtown atmosphere - but the back dining room is still upscale enough for a special occasion. And if your boss wants something more casual, there’s bar area up front where he or she can have a burger and several martinis.
Cote is an upscale Korean barbecue place in Flatiron, and they serve classic steakhouse cuts that the servers grill in the middle of your table. The whole place is dark and sleek - and it’s just upscale enough for any kind of business-y occasion. That being said, it isn’t formal or stuffy, and, if your boss wants to, he or she can order several rounds of pink slushy drinks. It can be a little tough to get a table at prime hours, but either book a few weeks in advance or convince your boss that all the cool people are eating at 5pm now.
At Sushi Ishikawa, there are only two things you can order: a 12-piece omakase for $85, or a 15-piece one for $125. You’re not paying, so opt for the more expensive one on your boss’s behalf - it will come with things like uni, truffles, and caviar, and it’ll cause people to stare and wonder how they too can eat such things. Reservations here are pretty easy to get, although you should book counter seats if you want to give your boss the full experience of having pieces handed over by a chef.
If your boss often looks for the opportunity to mention how long he or she has lived in this city, try Il Buco. It opened over 20 years ago, and it’s been serving great Italian food ever since. The dimly-lit space is both charming and romantic due to the fact that used it be an antique store, so it’s particularly good for something like an anniversary dinner or special date night.
Pasquale Jones and Charlie Bird are two of our favorite restaurants downtown, and Legacy Records is sort of like their older sibling who has slightly more money. It’s a big space in Hudson Yards with a green-and-gold color scheme, a long wine list, and a menu of things like lobster risotto and a whole lacquered duck. They also do a crudo tasting with things like uni, crab, and tuna belly, and that should be on your table. Or your boss’s table.
Casa Apicii is in the bottom of a Greenwich Village townhouse, and it doesn’t look like much from the outside - but walk inside and you’ll find a big dining room with velvet chairs, high ceilings, and some leather banquettes. You’ll also find some very good Italian food, including pastas that your boss will text you about mid-meal. The best part is that it isn’t very hard to get a reservation. So keep the Casa Apicii number on speed dial.
Your boss needs a place with a view, but you’ve tried and failed to book a table at Manhatta. Try Celestine instead. It isn’t on a rooftop - but it’s at the edge of the Dumbo waterfront, and it has a great view of the East River and Manhattan. The food is Mediterranean, and while it isn’t perfect, it’s pretty solid overall (we particularly like the Turkish dumplings). It’s also a nice minimalist space with high ceilings and big windows - and despite the fact that the view is probably worth several million dollars, reservations aren’t too tough.
Does your boss want to eat in Williamsburg because he heard it’s cool? If so, you have a few options. There’s Lilia - but unless you have dirt on one of the hosts, you aren’t getting a last-minute reservation there. So go for Reynard. It’s the restaurant in the bottom of the Wythe Hotel, and it looks like it could plausibly exist in Hogwarts, with high ceilings, big windows, and exposed brick walls. Also, it’s never really as busy as it should be. The food can be on the heavier side, but if your boss likes eating birds, he’ll appreciate the whole chicken that gets roasted over an open fire.
If your boss asked for a table at a place that’s “fun” and “downtown,” but you suspect that a spot like Tijuana Picnic will be a little too much, try Simon & The Whale. It’s in the bottom of the Freehand Hotel, it gets pretty loud and lively, and your boss can eat some good and interesting Mediterranean food here, like smoked mussels or pork collar milanese. The space is also somewhat luxurious, with low ceilings, tiled walls, and lots of wood paneling, and there’s a rooftop bar (Broken Shaker) where your boss can have a tiki drink after dinner, as long as he or she doesn’t mind waiting in line.
Mimi is a tiny French restaurant in Greenwich Village where the servers wear T-shirts and the menu consists of things like uni with egg yolk and wasabi, lamb tartare, and soft shell crab with blood sausage. All of the food is pretty unique and inventive, and the atmosphere feels sort of like a small house party downtown where everyone is seated at a table. It’s a fun place, and your boss will enjoy telling people about this little spot she discovered, which has actually been open for years.
Your boss would like to get dinner near a Jenner at Carbone, but that just isn’t in the cards tonight, or any night for at least the next month. Here’s the good news: Quality Italian has a much bigger space, the food here is solid, and getting a last-minute table isn’t difficult. So if your boss wants red-sauce Italian in a place where he or she can drink expensive wine or get a few rounds of shots, book a table here. It’s also in Midtown, which is another selling point (for anyone who works in Midtown).
Steakhouses typically feel like they were designed for oil barons and/or lonely tech billionaires who no longer have any friends. But Quality Meats is different. It feels like it was designed for a tech billionaire who has plenty of friends. It’s big and loud, it isn’t very stuffy, and, much like Quality Italian, it looks like it could be located in the bottom of a casino in Las Vegas. Your boss will have fun here, and also probably spend a decent amount of money on large cuts of red meat.
Does your boss want to feel like Poseidon? Book a table at Marea. It’s an upscale seafood spot just across from Central Park on 59th Street, and it’s a good place to eat some crudo, oysters, and caviar. This place also serves a lot of very good pasta - recommend the one with octopus and bone marrow, and there’s a chance you’ll get promoted. You probably won’t, but it’s important to hope for things.
Maialino is the ideal place to eat with someone who just recently stopped going below 14th Street. We aren’t saying it’s uncool - it’s just nice and wholesome-looking with its blue-and-white checkered tablecloths, and the menu has a bunch of pastas that pretty much everyone will like. This place is located in the bottom of the Gramercy Park Hotel, and it’s a good spot for your boss and a friend to eat some cacio e pepe while they talk about school districts.
The Clocktower is broken up into five different rooms, and they all feel like they belong in the home of a very rich English person who might try to hunt you. It’s dark and intimate, there’s a bar covered in actual gold, and the food is just as impressive as the space. The menu is English and American, with things like oysters, foie gras, duck, and steak - and you can also pretty much always get a table here.
Vaucluse is a fancy French place, but it isn’t as uptight as some of the other high-end restaurants in the area. Sure, there’s a prix fixe and a tasting menu, but you can also just order à la carte and have some steak and oysters. It’s good for a special occasion or a business dinner when you don’t necessarily want to spend $1,000 - although your boss could still spend that much on wine if he or she wanted to.
If your boss sometimes suspects that the skim latte you hand-deliver each morning was actually made with whole milk, Little Park might be the right choice. Many of the dishes here consist of fish or vegetables, so it’s perfect for someone who occasionally talks about going on a juice cleanse - although there are also some other options, like steak and duck. The space is in the bottom of a hotel in Tribeca, it has some nice big booths, and it’s decorated with earth tones, which your boss should find comforting.
Lafayette is a big, all-purpose bistro in Noho that’s essentially the Pepsi to Balthazar’s Coke. There are high ceilings and banquettes, and, like Balthazar, there’s also a bakery attached. The menu is comprehensive, with plenty of classic French options like escargots and moules frites, in addition to some other things like pasta and a burger. Book a big booth here and hope you’ll be invited this time, too.