Your boss gets paid more than you, and can afford to eat whatever they want. But at least you have youth. You can drink a 24-ounce beer and chase that with six shots of tequila and feel aces in the morning.
Keep that in mind the next time your boss asks you to find them the “perfect” place to eat dinner. And use this guide to find a place that’s just right - a restaurant that’s pricey but not insanely expensive, mature but not strictly for old people, and (most importantly) somewhere you can actually make a reservation.
Perfect For: Boss Who Wants Carbone
Your boss would rather be eating beside Kanye at Carbone, but that’s just not in the cards tonight. On the bright side, Quality Italian is a much bigger space, and you won’t have to get past a host who’s on the champagne-and-cigarettes diet. When your boss wants red-sauce Italian, book a table here. It’s in Midtown, and they can bring as many people and spend as much money as they want.
Perfect For: Boss Who Once Tried To Take You To Scores
Your boss is under fifty, and wants a steak. Or maybe they just feel like they’re under fifty and want to continue feeling that way. That’s when you send them to Quality Meats. It’s a steakhouse, but it’s less stuffy than a traditional one, and it wouldn’t feel out of place in the bottom of a Vegas hotel adjacent to a very classy strip club.
Perfect For: Boss Who’s Had The Same Expensive Handbag For Over A Decade
If your boss misses Bloomberg and Giuliani (and reminds you of this daily), Il Buco might keep them quiet for minute. It opened over twenty years ago, and it’s been serving good food ever since. Here, it’s upscale Italian in a romantic setting with downtown vibes. The space used to be an antiques store, if that gives you an idea of what’s going down.
Perfect For: Boss Who Looks Down On Your Whole Foods Sushi
Is your boss a pescatarian? Book a table at Marea. And if your boss only eats parrotfish crudo, Marea has them covered. (There’s a whole crudo menu.) But the thing you don’t want to miss here is the pasta. If the bone marrow/octopus one is on the menu, tell your boss to get it. This is a fancier option, and it’s right below Central Park, so it’s good for something a little more formal.
Perfect For: Boss Who Asks For Room-Temperature Water
Before your boss becomes an old person who complains about the temperature in Daniel, book them a dinner at Vaucluse. The food is French, but the experience isn’t as uptight as it is at other fine-dining places in the area. It’s good for a moderately-special occasion or a formal business dinner between a few people who are getting up there in years but consider the people at Per Se the true fuddy duddies.
Perfect For: Boss Who Gave Kids Gender-Neutral Names
In a word, Maialino is “nice.” The proprietor (Danny Meyer, bringer of Shake Shack) is all about hospitality, so expect warm service and family-friendly vibes. The restaurant’s located in the bottom of the Gramercy Park Hotel, the dining room is unpretentious, and it’s a good place for your boss and a friend to pick at a few somewhat-expensive pastas while they talk about school districts.
Perfect For: Boss Who Wants To Hide From Spouse
The Clocktower is broken up into five different rooms, and they all feel like they belong in the home of a very rich person who once spent a semester abroad in London and won’t let anyone forget. The good news is, the English/American food is as good as the decor. Also, it’s dark and intimate, and there’s a bar covered in actual gold. It’s called the Gold Bar.
Perfect For: Boss Who Had More Hair And Less Money When Nobu First Opened
When your boss peaked fifteen years ago, they didn’t have enough money to appropriately express their swagger. Now they’re loaded, and that’s no longer the case. Send them to Nobu. Nobu’s rock shrimp and miso black cod are probably half the reason your boss wanted so badly to climb the corporate ladder, so be like the Make A Wish Foundation For People Who Probably Don’t Deserve It, and get them a table there. The sushi isn’t bad either.
Perfect For: Boss Who Smokes And Pronounces Givenchy Correctly
Just so you know, “tortue” is French for “turtle.” Don’t go to France and think you know more French than you do. (That’s not a good game plan.) The name of Le Turtle is just one of many random elements of a restaurant whose strangeness was probably meant to appeal to fashion-y people. About a third of the ingredients on the dinner menu will be unexpected or unfamiliar, but the food is surprisingly good. If your boss wears all black at least twenty percent of the time, send them here.
Perfect For: Boss Who Goes To Clubs But Shouldn’t
If shoes with bright red soles or untucked button-down shirts are key elements of your boss’ weekend wardrobe, get a table at La Sirena. It’s only a few blocks from the Meatpacking District and there’s a Tao on the same block, so if your forty-something boss wants a “scene,” they'll enjoy eating pasta here.
Perfect For: Boss Who Assumes They’re Just As Important Outside The Office
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 there’s a bakery in front. This place was built with people like your boss in mind. If you get them a booth where other people can see them, they will be grateful (although they might not express it). The menu is comprehensive, with plenty of classic French options and some pastas as well. Your boss will find something to eat. If they’re going through a midlife crisis and they’re feeling uninteresting, they might get the frog legs.
Perfect For: Boss Who’s Been Known To Say, “This Is Fun, Right?”
If you need somewhere between The Smith and fine dining, this is it. The NoMad’s a little too pricey and formal for actually-fun people, but your boss will appreciate the truffled chicken and the classic rock soundtrack. If they’re looking for somewhere lively, the NoMad and its bar draw steady crowds. Also, the expensive-looking decor will assure them that this is a worthwhile dining experience, and you won’t get shouted at the next day if they order the aforementioned chicken.
Perfect For: Boss Who Asks For Dry Whole Wheat Toast
If your boss has ever referred to a “beet” as a “beetroot,” Little Park might be for them. They’ll appreciate the excuse to say “beetroot” without any shame, and they can have it as a tartare alongside some carrot risotto and a watermelon steak. Most of the dishes at Little Park consist of fish and vegetables, so this place is perfect for the boss who often suspects that their skim milk cappuccino was made with whole milk. It’s also an attractive space in the bottom of a Tribeca hotel, so that’s just a win all around.
Perfect For: Boss Who Wants To “Hang”
Your boss probably isn’t the Brooklyn type. Maybe Park Slope, but we can’t really see them shooting whiskey at the Three Diamond Door. So if they’re feeling adventurous and they want to check out this “Williamsburg” they’ve heard so much about, book them a table at Lilia. It’s a big, bright restaurant off the Bedford L that would probably draw a lot of fire for unwelcome gentrification if the food weren’t so consistently excellent. It might not be authentic Williamsburg, but at this point, what is? Just tell your boss it’s the real deal and Uber them over the bridge.
Perfect For: Boss Who Asked To Go To A “Foodie” Place
Does your boss watch a lot of the Food Network? So much that they come into work in the morning asking if you saw all the crazy sh*t that went down on Chopped the night before but also isn’t Ted Allen such a dork but also sort of hot? Osteria Morini is the downtown restaurant to book for that upcoming client outing. It’s a good restaurant from a well-known chef who isn’t quite a “celebrity” so that’ll add some cred when the inevitable name dropping starts happening: “I just love Michael White restaurants.” Of course you do.
Perfect For: Boss Who Only Eats Santa Barbara Uni
Do you have one of those bosses who brags about spending exorbitant amounts of money on sushi? The kind that only eats sashimi and only sits at the counter? Well, when the inevitable call comes that you have to book an important dinner “somewhere expensive,” book 15 East with confidence. This is a sushi restaurant of the highest quality, with a nice, upscale room, and great tables for parties of four or larger. Will it be the same experience as eating hand rolls passed directly to you from the chef? No. But it’ll do the job.
Perfect For: Boss Who Wants To Wear A Suit Downtown
If you work for someone who just can’t get comfortable with the idea of hosting a business dinner sans jacket/pant suit, but also wants to seem cool and “in the know” about things other than jackets and pant suits, The Clam is the place to be. This restaurant nicely straddles the boundary between cute West Village spot and upscale West Village spot, and the food is very good. Just make sure everyone is down to eat seafood or at least not deathly allergic to it.