Food & Drink

The Best Date Bar in (Almost) Every Boston 'Hood

Published On 10/01/2015 Published On 10/01/2015
Courtesy of Dave Baldwin
Flickr/Bernt Rostad

Allston

Sunset Grill and Tap (address and info)

If you want to say “I have social skills, and I like good beer,” the chill vibe at Sunset is a fantastic place for a meet-up. The hearty entrees come in epic portions, and the fountains of brew flow so freely you’ll be able to have an entire conversation about JUST BEER if it turns out you’ve got nothing in common. It sends the message that you have taste, but aren’t overly desperate to impress someone you hardly know.

Flickr/Egan Snow

Back Bay

Bukowski Tavern (address and info)

There aren’t a lot of places you can go out for a casual drink in Back Bay, but of the ones there are, Bukowski’s tops our list for its top-notch beer selection and sophisticated diveyness. While we can’t endorse the blatant misogyny and horrific poetry of its namesake, we can certainly get behind the bar’s signature “surly service,” “sharing is caring” apps, and, of course, the peanut butter burger (with bacon, because duh).

Courtesy of The Liberty Hotel

Beacon Hill

The Liberty Hotel (address and info)

If you're looking to lock it down with someone special, you can't escape this up-cycled jail just a stone's throw from the MGH T stop (although, yes, we realize that it's technically across the street from Beacon Hill). The space  is home to two sleek lounges (the Liberty Bar and Alibi), an outdoor courtyard, and multiple restaurants, so not only can you sip punny cocktails (like the "Cool Hand Cuke") in a super-sophisticated atmosphere, but you can hop around without ever leaving the building. Don't have a date?  That's cool, too -- the Liberty attracts one of the best-looking clienteles this side of the Charles.

The Warren Tavern

Charlestown

Warren Tavern (address and info)

Not only is Warren casual enough for an early round get-together, its food and drink are pretty solid on all fronts (the chowder especially). While you could easily meet up for a quick brew, you could just as easily spend all night noshing on burgers in front of the roaring dining room fireplace. Just like George Washington did.

Courtesy of Alan Medvinsky

Chinatown

Q Restaurant (address and info)

In a neighborhood of ramen-slinging, cash-only noodle stands, Q is one of the more stylish options for a night out. Fast service, reasonable prices, and a slick aesthetic make the pan-Asian lounge a decent drink destination, and should you find that things are heating up, you can always extend your time together and order a hot pot.

Flickr/ Jan Mark Holzer

Downtown

Highball Lounge (address and info)

Nine Zero Hotel’s cocktail lounge is more fun than fancy, featuring everything from rubber duckie-adorned martinis to a Spin the Wheel-style drink selector for the indecisive. Jenga, magnetic poetry, board games, View-Master toys, and rotating DJs all contribute to the playful vibe. That being said, it’s certainly not a gimmick; award-winning bartender Shaher Misif whips up one heck of a highball.
 

BONUS: jm Curley (address and info)

Or, if you’re looking for a post-Ant Man hangout spot, jm Curley serves up creative pub food (like the famous Curley’s cracka jack) alongside its rotating lineup of drinks. Also, there’s a strict no-douchebag rule, so the odds that you’ll be fending off date poachers is slim to none. And there’s enough noise to make any awkward silences bearable, but not enough to interfere with your conversation about the annoying physics of your new favorite superhero. (And hey, you’ll need another person to help you polish off that Monte Cristo.)
 

Dorchester

Ashmont Grill (address and info)

In a neighborhood of dive bars, the Ashmont’s outdoor patio and chill post-work crowd are remarkably date friendly. With Buck-a-Shuck Thursdays and six types of Bloody Mary available during weekend brunch, a few hours at Ashmont can become something of a sampling session, which is guaranteed to keep the conversation rolling.

Audubon

Fenway

Audubon (address and info)

From the owners of Trina’s Starlite Lounge comes Audubon, a Fenway bar that isn’t crowded with rabid Red Sox fans and actually serves some respectable beer. A few carefully curated cocktails and affordable-but-adorable sharing plates make it a game-day destination that’s less about gorging yourself on wings while glued to the TV than paying attention to your new friend. Which is good, 'cause who really wants to watch the Sox these days anyway.
 

Jamaica Plain

The Haven (address and info)

The Haven prides itself on its authentic Scottish “food, drink, and banter,” and it delivers on all fronts. The extensive beer list is organized by type and features a whole host of Scottish suds you’ve probably never had before, while the menu includes apps like Cullen skink, house-made lamb haggis, and truffle-honey rutabaga neeps with Drambuie butter. Also, desserts like toffee pudding and tipsy laird trifle. 

Ward 8

North End

Ward 8 (address and info)

Even if you’re meeting up post-Garden, remember: there’s nothing romantic about a sports bar. Unless you're on a date with Olympic gymnast and Needham's own Aly Raisman, then, maybe. Instead, head to this sleek-looking lounge, where you can swill a Scorched Earth or sip on a cold one while running through the play by play. Or discussing the intricacies of the balance beam, as it may be. They place has also been known to serve seasonal specials like absinthe or painkillers (in coconut goblets) just to mix it up. It’s a little dark, but that just adds to the ambiance.

Wink & Nod

South End

Wink and Nod (address and info)

Because it’s a great spot, PERIOD. Wink and Nod has out-of-the-park, 100%-from-scratch drinks, star chefs, a speakeasy-style entrance... what’s not to like? So, maybe it’s a bit classy for a first date, but if you’re on date two or three, or serious about him or her, it’ll be worth it. And if they bore you to death, at least you’ll get a kickass cocktail out of the deal. What’s more, the service is totally on point, and there’s something different every season. We like it so much we didn’t even want to tell you about it. But we did. So you’re welcome.

Courtesy of Melissa Ostrow

Fort Point/ Seaport

Committee (address and info)

This bar/restaurant combo just opened up in June, so not only are the odds good that your date hasn’t been there yet, but you’ll also likely earn bonus points for suggesting someplace new and different. Combine that with the cozy seating, eccentric collection of Tiki glassware (some Star Wars themed), friendly bar staff, and cheeky takes on classic cocktails, and you have all the ingredients for a great date bar. Also, there’s some decidedly romantic sidewalk seating.
 

Southie

Lincoln (address and info)

Sure, it’s not the classic Southie dive experience, but as we mentioned before, Pabst-coated sports bars aren’t exactly sexy. What is sexy is Lincoln’s gorgeous wood interior and its Monday night “Good Wine Cheap” event -- a weekly promo featuring discounted bottles that are perfect for the young, trendy, and not-quite-Newbury. The cocktails are cool but far from glitzy; the Crush on You, for instance (Ketel One, lemon, vanilla, and orange soda) makes it easy to send a completely un-subtle message to the person across from you.

Russell House Tavern

Harvard Square

Russell House Tavern (address and info)

Russell House has exposed brick, dark wood panels, and candlelit tables, all of which are just bonuses when you consider the bar’s popular oyster happy hour (post-11pm) and inventive cocktail list (try the End of Story or Jumpin’ Jack Smash). The first floor is a good place to watch the hustle and bustle of Harvard, but if you’d like a more laid-back evening, you can head downstairs for an atmosphere that’s more classy than collegiate. Trust us... it’s way better than taking her to the Wrong Kong.

Courtesy of Ames Street Deli

Kendall Square

Ames Street Deli (address and info)

From the folks behind Union Square's backbar comes Ames Street Deli, a tiny café that transforms into a cozy bar at night. Like backbar, Ames Street offers gourmand bar snacks “to share” along with a variety of strange brews and quirky cocktails. It’s a great-quality bar that doesn’t take itself too seriously, which is exactly what you want for the first time out with that special someone.
 

Inman Square

Trina’s Starlite Lounge (address and info)

Sure, it looks divey, but the southern food is to die for, and the drinks are anything but an afterthought. Pick up a StarPop (the bartender’s special fizz for the evening) or a rocking chair (black tea-infused bonded bourbon, Canton ginger Cognac, lemon) to start off the night. Trina’s also gets bonus points for having a delightful winter morning brunch; snag the Captain Crunch toast and chicken & waffles, then soak off your food coma at Inman Oasis.
 

River Gods (address and info)

River Gods is the kind of place where you can really hedge your bets. There’s beer, there are good cocktails on the menu, and there are people, but the bar isn’t as loud and crowded as, say, Brick and Mortar, and not as upscale and cocktail-centric as, say, Green Street or Craigie. It’s off the beaten path enough that it’s usually not as mobbed as other Central Square spots, and it’s the kind of place where you can figure out where things are going without laying all your cards on the table. If your romantic intentions fizzle, you can pass it off as the kind of place you’d take a good friend. If they fire, it’s nice enough that you won’t embarrass yourself.

The Abbey

Porter Square

The Abbey (address and info)

It’s casual and comfortable, with drinks and food that are basic without veering into boring. It feels more like your living room than a bar, even though it spans two floors and boasts a far more robust beer list than your fridge does. If bars could talk, this one would say, “I’m mature, affectionate, and looking for a stable relationship.” Not bad, right?
 

Davis Square

Spoke (address and info)

The tiny Davis Square wine bar is a bit on the fancy side, but that can’t hurt your chances, right? With everybody else headed to Saloon, it’ll not only be easy to find a table at this slick little establishment, but you’ll actually be able to hear each other talk! It’s not the best bet for beer (obviously), but if you’re into wine and cocktails, both are killer.

Brass Union

Union Square

Brass Union (address and info)

Brass Union feels like a laid-back house party, if that house party had an enviable craft beer program. The bar is covered with tabletop games and the indoor area features shuffleboard and Pac-Man -- there’s even a Pac-Man-themed dessert. Head to the outdoor patio for some fresh air and a shot at giant Jenga. It’ll give you both an opportunity to indulge your competitive side, or team up to topple other couples.

Sign up here for our daily Boston email and be the first to get all the food/drink/fun the Hub has to offer.

By day, Kim Prosise writes and edits content for clients around the world; by night, her circus freak alter ego performs high-flying feats of fantastic daredevilry. When she's not working, she's traveling, baking, or Dustbusting glitter. Ask her for facts about sea creatures.