Food & Drink

The Best First Date Restaurant in (Almost) Every Boston 'Hood

Published On 09/21/2015 Published On 09/21/2015

First dates are tricky: you don’t want to invest too much in a relationship that hasn’t even started, but you also want to make a good impression. As a lady who has been on many dates in many neighborhoods, I am here to tell you that the following restaurants do a nice job of walking that line. 

DAVE BALDWIN/THRILLIST

Allston

Deep Ellum (address and infoand Lone Star Taco Bar (address and info)
Learn a little about your date by having them choose between the two restaurants, under the same ownership and conveniently right next door to each other. The food is consistently delicious and creative at both, and neither one will break the bank. But is she a tequila and guac kind of girl, or more of a whiskey and burger type? Also, FoMu is only a few doors down and makes an excellent dessert. 
 

Back Bay

Zocalo (address and info)
Don’t want to give off sugar-daddy vibes to that random OkCupid person? Luckily, this cute little place plates fresh Mexican at first date prices. The dishes are Instagram-worthy, and the cocktails (like a fig Manhattan with molé bitters and a hibiscus margarita) feel more fun than fancy.

The Tip Tap Room

Beacon Hill

The Tip Tap Room (address and info)
The Tip Tap Room is the perfect combination of classic and distinct, and the ambiance is as good as the food. With a gorgeous wooden interior and huge garage door-style windows, it’s an ideal place to while away the last of the warm weather while sipping a Manhattan (or one of 70 beers!) and chowing down on wild boar tips.

DAVE BALDWIN/Thrillist

Charlestown

Pier 6 (address and info)
There’s nothing more romantic than a sunset over the skyline, except maybe a sunset shared over drinks and appetizers at a rooftop bar.
 

Chinatown

Gourmet Dumpling House (address and info)
Dumplings! GDH has some of the best bite-sized Chinese food in town. Also, if you move in together and microwave frozen dumplings for half your meals instead of actually cooking, you can always chalk your laziness up to the beautiful memory of the day you met.

Flickr/Massachusetts Office of Travel & Tourism

Downtown

Marliave (address and info)
For a classy lunch date look to Marliave, a sunny French place tucked away off Tremont St. It’s both upscale and unexpected, and odds are you’ll win points just for knowing it was there.
 

Faneuil Hall

If you’re going on a first date in Faneuil Hall, it’s probably because you’re a tourist (and/or from the suburbs) and don’t know any better. So, uh, yeah, don’t do that.
 

Fenway

Thaitation (address and info)
Thaitation has some of the best Thai food in Boston, and attentive service to boot. It’s bright, well decorated, and offers sidewalk seating during the warmer months.

Centre Street Cafe JP/Alex Gang

Jamaica Plain

Centre Street Café (address and info)
Even if you’re going on a more casual date, you still want the place to be cute enough to rub off on you. Centre Street does that, but in a good way.
 

North End

Carmen (address and info)
For Italian food in a cozy environment, Carmen is your move. Beware, though, you’ll need reservations if you want to beat the line. Follow it up with some of the neighborhood's best cannoli for a thoroughly Italian-themed outing.

Gaslight Brasserie du Coin

South End

Gaslight (address and info)
There are SO many places to choose from in the South End, but Gaslight wins for its laid-back atmosphere and modest pricing (for the South End, that is).

WILLIAM HORNE

Fort Point/Seaport

Trade (address and info)
Trade has a cool interior and a fun twist on small plates (try the sausage flatbread). And since it's a date, sharing is fun. Or if your date doesn't like to share, well, you've just learned something important. It’s also close enough to the water that you can see out over parts of the seaport, or walk around afterwards on your way to Drink.

Local 149

Southie

Local 149 (address and info)
Comfort food and craft beer should win the heart of any South Bostonian, and whimsical offerings like cast-iron Point Judith squid or flash-seared yellowtail are great for those with a slightly adventurous side.

WILLIAM HORNE

Harvard Square

Park Restaurant and Bar (address and info)
If you want to up the ante, Park Restaurant and Bar’s posh couches and swanky cocktails will make you feel like you’re hanging out in a James Bond film.
 

Kendall Square

The Friendly Toast (address and info)
Trust on this one. We already told you about the Sklarmaggeddon, right? But be sure to get there early -- it’s popular.
 

Inman Square

Tupelo (address and info)
This chic Inman Square spot pairs surprisingly affordable Southern comfort food with drinks in Mason jars. Whether you’re actually a lumbersexual or your plaid is just occasional, we recommend that you embrace the hipness and go.

Flickr/Christopher Schmidt

Central Square

Cuchi Cuchi (address and info)
This strange, sparkly mecca of cocktails, small plates, and waitresses dressed like flappers is fun without being too cheesy. The staff has enough of a sense of humor that they’ll entertain you even if your date turns out to be a bore. Plus, the banana bread is the perfect size to share. And if you make it past the first date, be sure to hit its sister spot off Inman, Dali.
 

Porter Square

Christopher’s (address and info)
The following is a real conversation:
Me: “What good first date restaurants are there in Porter?” 
Friend: “That you would actually go to, that aren’t Christopher’s?”
There you have it. So grab an English burger with avocado and follow it up with some live music at Toad.

WILLIAM HORNE

Davis Square

Foundry on Elm (address and info)
It’s classy bar food, but there’s something available for almost anyone, including oysters and a fun twist on bacon-wrapped dates. Also, you don’t have to be a mixologist to order a cocktail that you’ll enjoy. Try the On Fleek for something fresh and different.

WILLIAM HORNE

Union Square

Bronwyn (address and info)
If it was a really, really good date, you should be treating your companion to a really, really good brunch. The same applies if you're about to embark on one of those epic all-day dates that will no doubt involve day drinking, kayaking on the Charles, and a long "aren't we having so much fun today" stroll along the Esplanade. At Bronwyn, you can get maple-drenched German baked pancakes, sausage that is miles better than “breakfast sausage,” and surprisingly delicious grapefruit beer to wash it all down. And you can eat it all outdoors on the patio if you like.

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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.

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1. Deep Ellum 477 Cambridge St, Allston, MA 02134 (Allston Brighton)

Whiskey cocktails and Southern-inspired brunch fare are the name of the game at this Allston cocktail hangout. Deep Ellum's menu features seven types of Manhattans and more than 25 beers on tap, all worth exploring while you attempt to talk over blaring music (tip: get here early for a spot on the quieter, plant-filled back patio). While there is a solid dinner menu (go for the reuben sandwich and truffle gorgonzola fries), the brunch dishes are Boston bucket list-worthy and served seven days a week (!), and include a killer kielbasa & egg sandwich and a BBQ breakfast with braised pork shoulder, cornbread, and a fried egg.

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2. Lone Star Taco Bar 479 Cambridge St, Allston, MA 02134 (Allston Brighton)

Lone Star is the result of a collaboration between two dudes from Texas and Southern California, so you can feel pretty confident that they know their way around Mexican food. With a menu influenced by taquerias and markets in Austin, Dallas, and Mazatlan, Lone Star serves up a huge range of tacos, from carnitas and barbacoa to refried beans and huevos rancheros. They also do a killer breakfast menu (breakfast tacos! huevos rancheros!) and have an absolute ton of tequilas ready to pour.

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3. Zocalo Mexican Bistro & Tequila Bar 35 Stanhope St, Boston, MA 02116 (Back Bay)

Between its days in Brighton and now in the Back Bay, Zocalo has spent 25 years serving up faves like grilled jumbo shrimp in chimichurri sauce and chicken-stuffed batter-fried poblano peppers accompanied by killer margaritas.

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4. The Tip Tap Room 138 Cambridge St, Boston, MA 02114 (Boston)

Their concept is simple: cook up a variety of meat "tips", ranging from normal (steak and turkey) to exotic (Cilantro Serrano Kangaroo Filet), then pour more than 30 beers from their taps to wash it all down. And don't worry, if for some reason you're not interested in the tips or taps, they concoct a number of cocktails and serve other tasty eats, as well.

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5. Pier 6 Boston Waterfront 1 8th St, Charlestown, MA 02129 (Charlestown)

If you're looking for a restaurant with panoramic views of Boston Harbor, Pier 6 in Charlestown is for you. The three-floor restaurant focuses on New England fare and features a raw bar, a private dining room, and a roof deck.

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6. Gourmet Dumpling House 52 Beach St, Boston, MA 02111

If you're looking to stuff your face with delicious pork buns or other doughy comfort foods, this popular place serves cheap, authentic dumplings.

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7. Marliave 10 Bosworth St , Boston, MA 02108 (Downtown Crossing)

Downtown Boston’s Marliave might be the city’s fourth oldest city, but that only galvanizes its commitment to freshness both in décor and ingredients. The French and Italian restaurant creates all breads, desserts, sauces, pastas, ice cream, and stocks in-house, all of which combine to create the menu’s raw bar dishes, appetizers, eggs, pasta plates, risotto, meat and fish, sandwiches, and sides. The second-floor dining room is jam-packed with black tables, white-cushioned brown chairs, and a panorama of glass windows.

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8. Thaitation 129 Jersey St, Boston, MA 02215 (Fenway Kenmore)

Aiming to instill "more authenticity" in the old Brown Sugar space, a longtime BS chef has Bangkok'd the joint out, instituting a legit Thai menu and renovating the interior to "make you feel like you're in Thailand" with "sunshine yellow" walls, authentic Thai artwork, and sweet Thai background music (but oddly, nary a lady-boy).

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9. Centre Street Cafe 669 Centre St #A, Boston, MA 02130 (Jamaica Plain)

This bright, quirky spot sitting happily in Jamaica Plains boasts affordable breakfasts and Italian dinners. The menu's both vegetarian- and college kid-friendly (jackpot if you're both) with reasonably priced dishes like biscuits & gravy in the morning, pancetta-based burgers in the afternoon, and garlic-y corn risotto in the evening.

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10. Carmen 33 North Sq, Boston, MA 02113

Reservations are recommended at this cozy, elegant Italian restaurant, because there are only nine tables. Carmen's boasts a seasonal menu that features items like spice-crusted tuna, seafood brodetto, pan-seared duck, and sautéed haddock Francese.

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11. Gaslight Brasserie du Coin 560 Harrison Ave, Boston, MA 02118 (South End)

Parisian brasserie complete with cafe tables, communal booths, and an eclectic bar. Extensive wine list with over 20 French wines by the glass, and an impressive menu chock full o' Parisian delicacies.

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12. Trade 540 Atlantic Ave, Boston, MA 02210 (Financial Dist Waterfront)

Trade's industrial/wooded interior is quite the sight to behold until your meal arrives and you forget all about it. Award-winning chef Jody Adams features a menu of internationally inspired chow and specialty craft drinkables, wines and beer.

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13. Local 149 149 P St, South Boston, MA 02127 (South Boston)

The Local 149 puts the emphasis on "Local," offering a cozy and welcoming atmosphere for folks to pick from more than 20 brews on tap and eat delicious and fresh bar grub in South Boston.

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14. Park Restaurant & Bar 59 Jfk St, Cambridge, MA 02138 (Harvard Square)

This place is a class act with comfy couches and killer cocktails. It's got a romantic vibe, and a late night menu.

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15. The Friendly Toast 1 Kendall Square, Cambridge, MA 02139

The Kendall Square spinoff of the cult Portsmouth favorite, FT's Fri/Sat 24-hr, 150-seat full-service diner featuring a 22-seat bar, front lounge, and two dining areas adorned w/ lime green walls and hunter green vinyl seats and booths.

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16. Tupelo 1193 Cambridge St., Cambridge, MA 02139 (North Cambridge)

From the owner of Petsi Pies, Tupelo purveys "comfort food with a Southern flair" offering incestually authentic Louisiana recipes in a redwood-walled 45 seat space with white tile floors and chocolate wood tables.

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17. Cuchi Cuchi 795 Main St, Cambridge, MA 02139 (Kendall Square)

Opened in July 2001, CC serves up small plates (don't call them tapas here) and have a full liquor bar available with experienced bartenders making delicious specialty drinks.

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18. Christopher's Restaurant & Bar 1920 Massachusetts Ave, Cambridge, MA 02140 (Porter Square)

Christopher's in Cambridge offers up a delicious menu made up of American fare like wings and calamari, as well as great drinks.

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19. Foundry on Elm 255 Elm St, Somerville, MA 02144 (Davis)

A joint venture from two industry heavyweights who've dreamed of working together since high school, FOE's a brasserie-tavern hybrid (brassevern!) balancing oft-local hearty fare with delicious artisanal draughts.

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20. Bronwyn 255 Washington St, Somerville, MA 02143 (Union Square)

This cozy Union Square restaurant serves up modern twists on traditional and authentic German fare (borscht, massive bretzels, every wurst imaginable). And, in true German fashion, Bronwyn offers dozens of beers (by the liter, boot or bucket) from all over central Europe and New England. Owner Tim Wiechmann was aiming to imitate the atmosphere of a European dive or hostel with this location, and he totally nailed it with its nearly medeival look (dark, heavy wooden tables, worn-leather bar stools, rustic red and blue walls).

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