Whatever your relationship (or situationship) demands, we’ve got the restaurant for you.
LessSRV, or the Serene Republic of Venice, is a small plates spot with an exclusively Italian wine list, plates of pasta made with locally-milled flour, and a level of impeccable service that you might have heard doesn’t exist anymore. The food and drink offerings riff on baraci, the casual drink-and-snack bars you might pop into after work in Venice, but the vibe is extremely upscale South End neighborhood hangout. You could absolutely go here for a dolled-up anniversary or other special occasion.
If your idea of a good date involves eating wontons and bao while sipping on a mai tai, Darling is for you. The drink menu leans into molecular mixology, but they’re not all annoying about it. Think fizzy, bright, lacto-fermented tomato garnishes and sweet, aromatic clarified milk punch rather than foams and spheres. Their take on a lychee martini has a whiff of Jasmine and an almost creamy texture.
If you want to get into Oleana on a weekend night, plan accordingly. The relatively few tables in this small but much-loved Mediterranean restaurant on the edge of Inman Square book up quickly. It’s worth the effort, though, and it’s a little easier to get in during the summer when the backyard is open. Order some wine, and then pick out a few good-looking mezzes to share. If your date isn’t interested in the Sultan’s Delight, it’s kind of a red flag.
You’ll know you’ve found love when someone talks about you with even half the passion that Pammy’s regulars gush about this Central Square staple. The menu leans Italian, with little surprises every step of the way: gochujang in your bolognese sauce, tripe more velvety than you’ve ever had before, a humble beet smoked to perfection. Reservations are expected to order off the prix fixe menu, while those willing to wait for a walk-in table can order a la carte.
The Block At Woods Hill is the slightly more unbuttoned sibling to Woods Hill Pier 4. Slightly, because it’s still the sort of spot where you can celebrate a big anniversary by adding caviar to your seared foie gras. But you can also walk in for a spontaneous Tuesday date night and grab a casual glass of wine and some pig’s ear tater tots. The small plates here are plentiful, and it’s easy to make a meal out of them.
This small, family-owned restaurant tucked inside a darling pink building in Huron Village is a godsend when you’re looking for a quieter dinner. Our favorites from the menu include the roasted brussels sprouts with persimmon chips, the housemade sourdough bread served with a chive-forward compound butter, and the crispy petite chicken with root vegetable puree.
This is one of the most interesting restaurants in the city’s most interesting neighborhood. If you’re tired of planning out your conversation topics before your dates, come to this JP tapas spot that’s part-bookstore, part-record store, and part-living room of the chef-friend you don’t have. Hit up the patio if it’s nice out, the slope-side cabin of a dining room when it’s not, and always order the stuffed dates.
Just about everything is served family-style at this small Asian fusion spot in the South End. Expect fun cocktails, really great smells, and a lively atmosphere that always feels like a party. You should also know about the “great date night” special on Mondays-Thursdays, assuming you appreciate the idea of a fun, affordable prix-fixe menu with punny names. Which you should.
You can’t take the T to get to Celeste, but there are still plenty of opportunities to experience some unintentional shoulder-rubbing here since it’s only about the size of a train car. That said, we still really like this place. You’ll feel like you’re having an intimate date in the living room of a questionably legal pop-up restaurant, though government regulations will be the furthest thing from your mind as you enjoy some pisco sours, ceviche, and lamb stew.
The kind of American comfort food at Beehive works for most occasions, and date night is no exception. While the food is probably not going to make you commit the rest of your life to anyone, you’re also really here for the nightly live music, which is a rarity in Boston. Go out and have fun at this loud, underground restaurant that makes you feel a little cooler than you probably are.
O Ya is a special restaurant—the kind you reserve for that talk you’ve been putting off about getting engaged, buying a house, or whether having one kid is already one too many. The $295 omakase at O Ya is 20 perfect bites of fish, and you’ll want to take your time with each one to stave off the inevitable withdrawal you’ll go through when the meal is over.
Maybe you record tasting notes in a leather-bound notebook, or maybe you’ve been known to sip a glass of wine and say, “Huh, this one’s a little more red.” No matter how many outlandish adjectives you can or can’t come up with to describe what's in your glass, the people at this wine bar in the Fenway will help you find something you like. Just note that this dark, intimate spot is better for drinks and a bite than a full meal.
At Woods Hill Pier 4, the food and harbor views will constantly battle for your attention. This is a good thing, because both are excellent. Bring your date and order the smoky adelita margarita, the Cubano with ham and pork shoulder confit on the butteriest baguette, and any towering shellfish platter that comes, naturally, with Old Bay aioli.