There’s more to life than being cool. But when you need to plan a dinner with someone you know (or strongly suspect) is cooler than you, that’s easy to forget. So here’s a list of restaurants that will help convince this person that you’re actually the cool one. Some of these places are unique, some of them aren’t as well known as they should be, and all of them are cool enough to impress someone who has a list of their favorite art galleries in North Africa.
Steakhouses are usually only considered cool by bankers and people who unironically quote Entourage, but that’s because there aren’t a lot of steakhouses hidden in the back room of an Irish pub-like Bogie’s Place in Downtown Crossing. Slip through a curtain past the “Adult’s Only” sign, turn off your cell phone (it’s not allowed), and split a giant porterhouse along with a classic cocktail. This place is a lot cooler than what you usually find in the back of an Irish pub - an underage college kid relieving himself against a dumpster.
Pricey tasting menu places aren’t always cool. But that’s to be expected from restaurants that treat their food like museum pieces, where everyone around you is so quiet that you half-expect to see Tiger Woods trying for a birdie putt from the kitchen. But Asta in Back Bay is different, as you’ll be able to tell from the Ryan Gosling posters in the bathroom and lambskin-covered benches in the dining area. Come here when you want fine food like rabbit confit or seared foie gras with sunflower, but want it in a place that feels a bit like a bar.
Working shipyards can be either scary (if it’s the type of shipyard where things that are going to be on the morning news go down at 2am) or cool (if it’s the type of shipyard where a few of the old warehouses have been converted to art galleries). The shipyard across the harbor in East Boston is the latter, and it’s made even cooler by the presence of KO Pies, an Australian beach bar that’s been dropped into the middle of an industrial marina. Grab some meat pies, a beer, and sit on a picnic table as your cool friend tells you about the three months they spent as a stowaway on a container ship in the Indian Ocean.
Restaurants that can be mistaken for the bathroom are automatically cool, that’s just how the world works. No Relation is a tiny, nine-seat sushi counter hidden next to the bathrooms in the back hall of Shore Leave, which itself is a pretty cool tiki bar that will make you feel like a sailor working the spice route in the South Seas. The omakase costs about $100 per person, which definitely isn’t cheap, but it’s one of the better omakases in the city, and you get it in a casual place where you’ll probably end up chatting up the other people at the counter and the chef making your nigiri.
Saloon in Davis Square is one of our favorite speakeasies, a really dark basement that feels like the speakeasy behind the speakeasy, where the mob boss entertained corrupt politicians with the secret stash of whiskey and scotch. It’s even cooler on one Friday every month, when, for $48, you can get a two-course meal here followed by tickets to the burlesque show at the Rockwell, a theater down the hall.
If you’re not down for an actual burlesque experience, head to Cuchi Cuchi in Central Square instead. This place is burlesque-themed - not aggressively so in like a Hard Rock Cafe Meets Moulin Rouge way, but more subtly in that it feels a bit like something that would’ve belonged in New Orleans when French pirates were a thing. It has a ton of original cocktails and the menu is “global tapas,” which really just means they have a lot of different things to eat.
If you’re a musician or artist interested in becoming an icon of cool, then you should probably consider dying young in order to leave everyone wanting more. That’s basically the philosophy behind pop-up restaurants, too, and Tsurumen, in particular, which only plans to be in business for exactly 1,000 days. The noodles are outstanding at this tiny Davis Square spot and knowing that it’s going to be around for less time than James Dean makes it all the better.
Bow Market in Union Square - a converted storage garage that now houses a brewery, art studios, and shops that sell vintage Pez dispensers - is one of the coolest places in all of Boston. And Tanam, a Filipino restaurant that consists of just a single 10-seat table, is not only cool, but outstanding. Come here on Wednesday night for a communal meal of shellfish and pork that you eat with your hands off banana leaves, or on the weekend for a five-course meal of things like lobster spring rolls with caviar and spicy vinegar.
If you can’t get into Tanam because of that whole “single 10-seat table” thing, grab something to-go from one of the other vendors and head upstairs to Create. This tiny cocktail spot is as much of an art gallery as a bar, but as a bar it’s pretty damn good, because it serves exclusively draft cocktails put together by other bartenders from all over the city.
Brassica Kitchen & Cafe
Sometimes you might think Brassica in JP tries a little too hard to be cool. It’s a place where, if the table next to you is empty, your server will either casually lean against it while talking to you, or even sit down, as if to say “remember, I’m not a normal server, I’m a cool server.” But it isn’t entirely a put-on. It’s the product of a place that makes great food in a casual atmosphere, where the owner might stop at your table to let you know that the kitchen’s working out a new empanada dish tonight, and if any are plate-worthy he’ll send one your way. And if you really want to have fun, for $85 you can do a tasting of each of the 15 small plates on the menu.
We’ve always had great seafood, but unfortunately, it’s often been served in restaurants that look like a South Shore yacht club in 1982 - a lot of ships-in-a-bottle and creepy statuettes of old fishermen that are probably cursed. Saltie Girl, though, is the coolest oyster bar in the city, a place that feels like a seafood-themed runway during fashion week. The menu is great too, with a lot of things like torched salmon belly that you wouldn’t normally find in more traditional seafood restaurants.