Your date is going great. You didn’t awkwardly bump heads when you hugged hello. Your shirt remains free of tomato sauce stains. And you only spent 10 minutes repeatedly asking each other if you saw that new show on Amazon Prime, and then replying “Oh, no. But I’ve heard good things” (this is well under the national average of 27 and a half minutes).
But where do you go next?
This is not the time to drop and break your phone while nervously searching around for nearby spots. And if you do your homework beforehand, you won’t have to. Here are our favorite One-Two Punches - bars and restaurants within a few blocks of each other that work perfectly as part of the same itinerary. We can’t promise these plans will convince someone to go home with you, but we can promise they’ll be a rock solid foundation on which to seal the deal.
Italian restaurants and dates go together like pre-tiger attack Siegfried and Roy. SRV in the South End is one of the very best places for pasta in the city, with an extensive wine list, great small plates, and plenty of romantic outdoor seating during the good weather. Definitely get the truffle risotto.
Even if jazz isn’t really your thing, you can probably appreciate a no-cover club that’s been around so long it can start collecting social security. So after SRV, head across Mass Ave. to Wally’s, where you and your date can re-enact some scenes from La La Land and figure out which of you takes music way too seriously.
If you want to come off as cool during a date, you could steal some pithy tweets you read at lunch and pass them off as your own jokes. Or you could pick a new restaurant with a great menu and a space that feels like an art school party where no one’s trying too hard. Celeste in Union Square has a really interesting menu of ceviche and Peruvian stew, and it’s in a tiny little space that’ll keep things intimate but casual.
After eating every ceviche on the menu at Celeste, head down Bow Street to Thunder Road. No need to worry about recycling Twitter jokes here, because there’s a live indie band just about every night, so you won’t even need to talk to each other. There’s a cover, but it’s rarely more than $10.
It is possible that your date gets nightmares after staring at and eating the roasted pig’s head at Craigie On Main in Central Square. But think of that as an opportunity to overcome some challenges together. There are plenty of other great options on the . menu, so get the fried Essex clams if the pig freaks you out too much.
If you’re worried about being chased by the ghost of the pig whose head you just ate at Craigie, go hide in Brick and Mortar, a speakeasy you access through the unmarked door next to Central Kitchen. It’s got creative cocktails, good small bites, and hardly a single person who’s likely to spill a drink on you. Even if the pig ghost does manage to track you down, this place is so chill that he’ll probably have a couple of martinis and forgive you.
The decor at Yvonne’s Supper Club in Downtown crossing is elegant bordering on ostentatious, which gives you plenty to talk about during your date. Of course, after you enter the restaurant through a faux-hair salon, the Mediterranean-ish menu keeps things interesting, too. We like to stick to the small plates and toasts (particularly the wasabi lobster), but you can also go big with one of their feasts for two.
You’ll want to balance out Yvonne’s with something a little more low-key, so head to Haley.Henry in Downtown Crossing. It’s an unpretentious wine bar, and the perfect place to discuss the artistic value of the Bill Murray watercolor you just saw at dinner.
Your relationship won’t work if you guys don’t learn to share, so hit up Banyan in the South End, which has an extensive dim sum menu that’s designed for sharing. Split the KFC bao (way better than anything they actually serve at KFC) and have a drink in a restaurant that looks like a tree house in the mountains outside of Seoul.
Just a five-minute walk from Banyan you’ll find Wink And Nod, which is dark, fancy, and looks kind of like a cocktail den in Vegas (one of the classy ones the Ocean’s 11 guys would go to, not literally every other place in Vegas). In other words, if the date went so well that if you’re thinking of eloping in Vegas, then this is a good place for a test run. If scotch is your thing, you’ll have over 100 options here, but you should lean towards the cocktails, which are prepared with homemade cordials.
Fort Point / seaport
A date isn’t necessarily a good time to take risks, so play it safe with wine and pasta at Sportello in Fort Point. Start with the spicy tomato soup and make sure to try the braised rabbit strozzapreti. As an added bonus, most of the seats here are situated along a long, snaking counter, so if the date isn’t going well you can just turn around and talk to the stranger on the other side of you.
Trust is the most important part of any relationship, and there’s no better way to show how trusting you are than by going to a cocktail bar that, instead of giving you a menu, asks you to simply give the bartender a little guidance and let them do their thing. It also doesn’t hurt that Drink is right beneath Sportello, so you won’t lose any momentum changing venues.
With cherry blossom wallpaper, caged lanterns, and wooden walls that you want to say are cedar, but only because cedar is really the only fancy wood building material you can name, Basho is one of those casual-cool places that will make you realize how little actual effort you put into decorating your own place. It’s a Japanese restaurant in the Fenway with moderate prices and a wide-ranging menu (we’re fans of the miso black cod), so your date will still be able to eat something even if they don’t like sushi (though that may be a sign that you need to find a new date).
Across the street from Basho you’ll find Fool’s Errand. It’s a little cocktail bar with small bites, glimmering chandeliers, and a bathroom you’ll have to wait in line for because everyone’s taking pictures of the photo that hangs above the toilet of Snoop and Martha Stewart holding each other in a loving embrace. This place also doesn’t have any seats, so you’ll already be on your feet and ready to make an escape if you find out your date doesn’t like brown butter pumpkin croquettes either.
After The Table At Season To Taste, keep the cool little local spot thing going by heading to UpperWest. It’s a cocktail bar hidden in the basement of a veteran’s hall, and you’ll get points just for knowing it exists.
Waypoint in Harvard Square is an untraditional seafood restaurant with great cocktails, a menu that stretches from clam pizza to Maine lamb shoulder, and crowds of people who are always having fun. In other words, if you and your date don’t have a good time here, there’s pretty much no hope for you and you should break it off now.
If you two did have a good time at Waypoint, we’re betting that their extensive selection of absinthe cocktails had something to do with it. Slow things down with some beers at Beat Brew Hall, which has over 20 rotating taps and live music.
A chill, tiny ceviche bar with an outdoor patio and (appropriately for Newbury Street) pop art all over the walls probably isn’t a place you’re going to be in any hurry to leave. Luckily, Puro’s extensive menu of small plates gives you a reason to stay a while. Start with the sea bass ceviche and go nuts from there.
Stick with the Latin theme up the street and around the corner at Lolita, a neo-gothic dungeon of a restaurant/lounge that serves 11 different types of margaritas. There might be a line outside on a weekend, but after chilling at Puro for so long, you probably won’t mind something with a little more buzz.