The Hopeless Romantic’s Guide to Dating in Boston

Edited by Andrea Timpano

Photo illustration by Benjamen Purvis / Getty Images

Masks. Boosters. Zoom. Dating life sure is different now. Yet some things never change: We all still want a little love—and some sound advice on where to find it. So here’s how to do just that. From casual spots for nailing that first impression to cozy hideaways for spicing things up with your longtime better half, check out 20 places every starry-eyed city dweller should know by heart.

Illustration by Mark Matcho

First Dates

What impression do you want to make? We’ve got a plan for that.

I’m a Foodie

With 19 food and beverage vendors, seating for about 500 diners, and an LED entertainment system displaying all the local games, High Street Place—opening at long last this March—has no shortage of conversation starters. Go halfsies on a pie from Tiffani Faison’s old-school pizza-and-grinders spot Tenderoni’s, one of three new businesses the Top Chef alum is debuting at the food hall, or sample a spread of Insta-worthy doughnuts from Lionheart Confections; options abound.

I’m a Wine Lover

Maybe you bonded on Hinge over your mutual love for cool-climate Syrah; maybe you don’t know your Chardonnay from your Chenin Blanc. Either way, you’re in good hands at Cambridge’s Dear Annie, where Lauren Friel (of Rebel Rebel) and Andrew Brady and Sara Markey (of Field & Vine) serve up a hyper-curated selection of natural wines along with pescatarian small plates. Pull up a couple of chairs at the new bar’s cozy communal table, soak up the dreamy candlelight, and let the vino take the edge off.

I’m a Kid at Heart

A surefire cure for the first-date jitters? Channeling all of that nervous energy into a rousing round of “tech-infused” indoor mini golf at Puttshack, opening later this year in the Seaport. Screens guide you and your date through the game, and the balls keep track of scoring for you—so you can focus all of your attention on your flirty banter. We’d call that a win.

I’m a Style Icon

If you want to cop your date’s impeccable taste—and prove you’ve been paying attention—follow their lead on a stroll through the small but mighty storefronts at Union Square’s Bow Market. Whether it’s a vintage cookbook from Blue Bandana Relics or Crane & Turtle’s beautiful, minimalist tableware, you’re sure to come home with a treasure or two—and, if you’re lucky, plans for a second hang.

I’m One Cool Competitor

If you and your prospective mate share a competitive edge, there’s no better spot for a first meetup than Indie Trivia at Aeronaut’s Somerville brewery, a weekly throw-down hosted by different trivia-master volunteers who craft tricky rounds and questions entirely on their own. From the moment you land on the perfect team name to your glorious end-of-night victory, nothing is more romantic than besting a bunch of strangers. —Alyssa Vaughn

Photo by Kristin Teig

Date Night Confessions

As told to Brenna Donovan

Christopher Myers and Joanne Chang
Co-owners of Myers + Chang

Christopher Myers: A date doesn’t have to be complicated. Our ritual is we go to the fish store, we decide what dish to make, and then we launch into a long discussion about which starch we’re going to have. And we really should disabuse ourselves of that custom because rice wins every time.

Joanne Chang: I go through the motions of pretending like we’re going to consider maybe potatoes or something, but no.

CM: A meal without rice is not really a meal.

JC: If we’re going out, it’s pretty casual in that we’re not making a reservation for primetime 7 p.m. on Saturday. That’s not really our thing. We like to eat pretty early and sit at the bar and watch people. Plus, you can sit closer together at a bar.

CM: I don’t think we have a date where there’s not a walk involved, especially after dinner. We call it a postprandial. So that occasionally means bringing a backpack for better shoes.

JC: That’s one of the reasons to eat early, so that you’re not walking around at like 10 at night. And I think it’s good for your digestion, too.

Love in the Time of COVID

Some etiquette tips for dating in the new normal.

Share Your Status

Vaccination status can make or break a budding relationship, so Jodi Smith, president and owner of Marblehead-based Mannersmith Etiquette Consulting, suggests broaching the topic as early as possible. Pro tip: Instead of asking your date to fess up, try sharing your status first. It’ll give your love interest a convenient opportunity to return the favor.

Suss Out Risk

In this phase of the pandemic, when some are clubbing and others are still sticking to takeout on the couch, how do you determine your date’s attitude toward risk-taking? “Ask, but don’t interrogate,” Smith advises. In other words: Don’t demand every detail of their recent whereabouts. Instead, pose more casual questions (How did you celebrate the holidays? How many people were there?) that will help paint a picture of their risk tolerance.

Set Boundaries

Should you decide to meet IRL, don’t leave your date wondering how COVID-cautious you’ll be. “Having good manners means making those around you feel comfortable,” Smith says. “And one way you can do that is by letting them know what’s expected of them.” From your thoughts on crowded places to whether you plan to wear a mask throughout your meetup, leaving nothing to the imagination is, in this case, a good thing.

Brush Up on Small Talk

After months of isolation, the idea of sustaining a multi-hour conversation with a stranger can seem insurmountable. To keep awkward silences at bay, Smith recommends checking in with yourself before the big event. “Take the time to think about what makes you unique,” she says. “What are the things that get you excited and happy?” These should be your talking points. —A.V.

Illustration by Mark Matcho

Double Dates

Gather your sweetie and your squad for one-of-a-kind group hangs.

Get Soulful at a Jazz Club

The long-awaited reopening of Scullers Jazz club last fall kicked off with an impressive lineup of musical greats including Grammy-winning vocalist Dee Dee Bridgewater and pianist Bill Charlap. Now, the legendary jazz club on the Charles is back in the swing of Friday- and Saturday-night shows. Snag tickets for a café table near the stage to get up close and personal with some dulcet tones, or opt to enjoy the performance from the Miles Davis Mezzanine—it’s just steps from the bar.

Take a Crack at an Obscure Olympic Sport

Down to bundle up? Try your hand at curling courtesy of Snowport, the Seaport’s take on a winter wonderland. Groups can reserve free 30-minute slots, which include brooms and stones, plus a freshly sanitized (and socially distanced) lane. Bonus: For the uninitiated, curling lessons are available on select Saturdays through mid-February.

Go on a Culinary Adventure

The staff at Tasting Counter encourage you to leave your wallet at home for their two-hour tasting-menu experience. Reserve a maximum of four all-inclusive tickets on the Somerville standout’s website, prepay online, and trust the rest to the hosts upon being seated at the restaurant’s U-shaped counter, where the kitchen in the center is on full display. While the meal’s nine courses—which are always a surprise to diners—highlight seasonal ingredients and flavors, guests can also create an online profile to help the chefs understand their palate and preferences. Yum.

Explore Your Artsy Side

Feeling creative? Rally your crew for an afternoon at the Clayroom in Brookline, where you can book a private pottery-wheel lesson for up to four people. With multiple two-hour time slots seven days a week, there are plenty of opportunities to get crafty with your group. Once your newly formed masterpiece is fired in a kiln, you can come back to pick up your creation or reserve another time slot to paint it.

Test Your Wits

Escape rooms may have fallen to the wayside at the height of the pandemic, but Trapology Boston devised a way to keep the fun going during COVID: Rather than finding your way out of a small indoor space, the company challenges teams of six to uncover clues and solve puzzles on the city’s streets, with the help of augmented-reality technology. Choose from three outdoor options, hit the pavement, and see if you can complete your quest in the allotted 90 minutes. Ticktock. —Madeline Bilis

Photo by Drew Altizer

Date Night Confessions

As told to M.B.

Paul and Sandy Edgerley
Cofounders of the ‘Quin House

Sandy Edgerley: For us, date night often revolves around a meal. We love all the great restaurants in town, and Davio’s has always been a favorite.

Paul Edgerley: I think we’ve been going there since when it was on Newbury Street, so that’s got to be 30-plus years.

SE: Our favorite waiter, Tonino, always takes great care of us.

PE: He has an extraordinarily warm, big personality, and he’s been with Davio’s since the early days. We’ve got one of a couple of tables we sit at, and they’re in his section. He knows that Sandy is going to have her Diet Coke with two lemons, and when we sit down, it’s there. I’m likely going to have an 18-Year-Old Macallan on the rocks, and it’s there. So there’s a familiarity. It’s that old Cheers, everybody-knows-your-name feeling.

Photo by Massimo Borchi/Atlantide PhotoTravel/Getty Images

Survey Says…

What our slightly nosey, all-in-good-fun dating poll reveals about Boston.

32 Percentage of Bostonians who think the Hub is a good place to live if you’re single and looking.

64 Percentage of Bostonians who reject the idea of love at first sight.

1  Ranking of the Esplanade, which was voted the most romantic spot in Boston.

62  Percentage of Bostonians who said “Nay” to workplace romance.

92  Percentage of Bostonians who feel the pandemic has made dating more difficult.

5  Percentage of Bostonians who have never used a dating app.

55  Percentage of Bostonians who named Hinge as their dating app of choice.

25  Percentage of Bostonians who believe in soulmates.

Illustration by Mark Matcho

Rekindle-the-Flame Dates

It’s never too late to spark fresh romance.

Heat Things Up in the Kitchen

Cooking with the person you love can be super romantic. But if it’s time to get out of your own kitchen, bring your appetite to a getaway at Lexington’s Inn at Hastings Park, where you and your sweetheart can indulge in a private cooking class to add some new dishes to your date-night-in repertoire. Hungry for more? The inn’s immersive cooking weekend boasts 20 hours of culinary education complete with a farm tour and a four-course tasting dinner.

Stoke Your Passion for Live Music

If you spent your twenties rocking out in clubs, rediscover the rush you got from seeing your favorite band (or find a new favorite) at Roadrunner, Allston-Brighton’s newest concert hall. Named for the classic Modern Lovers song about Massachusetts, this 3,500-person, general-admission venue is set to start its run of shows in March. And you can dance the night away for a good cause—currently, a portion of proceeds will go to the Shout Syndicate, a local fund that supports youth-led arts programs.

Get Cozy in a Custom Salt Cave

Tap into some relaxation with your beloved and re-create the feeling of breathing in salty ocean air at the only custom-built salt cave in Boston at G2O Spa + Salon. Leave your phone at the door, kick back in the reclining chairs, and take in the negative ion–charged air to cure what ails you (halotherapy is said to offer relief from respiratory and skin conditions, and there’s even talk that it reduces stress). COVID guidelines allow just one group at a time, which means a more intimate experience for you and your companion.

Reconnect in the Company of World-Class Art

Caught up on the documentary about the Gardner heist? Skip Netflix tonight and see the scene of the crime IRL at the museum’s Free First Thursdays, where admission is comped on the first Thursday evening of each month (and the museum stays open until 9). Sneak a kiss beneath the stone archways overlooking the Italian Villa–inspired courtyard, or wander the halls and marvel at the masterpieces—there’s plenty to see beyond the empty frames.

Bond Over an Outdoor Adventure

Spending a lazy afternoon picnicking beneath fluffy clouds is a true romantic’s dream. Once the snow melts, fill your wicker basket with snacks and head for Spectacle Island, just a quick ferry ride from the city. Explore its 114 acres until you find the perfect spot to spread your checkered blanket, or opt for a gazebo with a picnic table. And make sure you end the afternoon by walking hand in hand along the beach—the best way to soak in skyline views. —Brenna Donovan

Courtesy photo

Date Night Confessions

As told to Andrea Timpano

Wayne and Jacqui Budd
Senior counsel for Goodwin Procter and board president of Dress for Success, respectively

At our age, date night is almost every night. But when we are home alone and have no obligations, we have dinner. We have a little routine. First, we drink a toast to each other, usually with wine. His favorite is red, and mine is white. But it depends on what we’re eating. I will open the wine based on what I made for dinner—or what we’ve taken out for dinner, let me be honest. These days, it’s either/or. We live both in Boston and on Martha’s Vineyard. When we’re in Boston, we order from Picco. Here on the island, where we are now, we get takeout from the Barn Bowl & Bistro or Winston’s Kitchen, which is new. They’re really good.

Then, when we eat, we always have candlelight. That’s important. And we play our favorite music, which is anything from Quincy Jones, Chris Botti, or Sting. And, you know, we just have a leisurely dinner by ourselves and enjoy conversation. We’ve been doing that for years. It’s just special to have that downtime together.

Photo by Frederic Reglain/Alamy Stock Photo

The Singles Scene

On the hunt for love? Skip the swiping and head to these hotbeds of romance instead.

Abe & Louie’s

Who You’ll Find: A mix of vest-clad finance bros and dressed-to-the-nines, slightly more (ahem) mature patrons.

The Vibe: With dark-wood-paneled walls, white tablecloths, and leather booths, this Back Bay steakhouse gives off serious “I dabble in the stock market” energy. The lively bar area is ripe for hobnobbing, martini in hand, and if you’re lucky you may spot a celebrity in your midst; Abe & Louie’s is known for attracting high-profile clientele.

The Liberty Hotel

Who You’ll Find: Well-dressed thirty-somethings who have outgrown the club scene but aren’t quite ready to turn down the music.

The Vibe: This former jail turned hotel caters to more than just tourists. With strategically placed lounge tables and a hopping bar, the wide-open lobby space makes easy work of mingling with eligible locals. Want something a little more moody? Head downstairs to Alibi, the jail’s old drunk tank; now a popular watering hole, the dimly lit hangout offers close quarters perfect for brushing shoulders with a handsome stranger (a doctor from MGH, perhaps?).

Boston Ski and Sports Club

Who You’ll Find: Endorphin-seeking athletic types looking for someone to bond with over postgame beers.

The Vibe: From basketball and soccer to kickball and ultimate Frisbee, you’re sure to meet the jock you’re searching for when you join one of the many leagues offered by the largest adult sports organization in Greater Boston. And it’s not all team activities; sign up for a weekend ski trip or swing by a club-sponsored event at a bar to meet prospective love interests off the field. —B.D.

Illustration by Mark Matcho

Solo Dates

Among the benefits to going it alone? You get to do exactly what you want.

Make It a Spa Day

Let’s be honest: Does anyone even like couple’s massages? Skip the cliché and book a pampering party for one at the new VIO Med Spa, which began welcoming clients last October. Located some 15 miles north of the city in Burlington, the tranquil refuge offers a full roster of must-try restorative treatments, like the HydraFacial MD—a three-part service in which your skin is cleansed, exfoliated, and infused with antioxidant-rich serum in an hour or less.

Flex Your Creative Muscles

It’s hard to beat the satisfaction that comes from fashioning something with your own two hands. Why not craft your next masterpiece with an assist from the experienced pros at the historical North Bennet Street School? Founded in the late 19th century, the revered North End trade school recently relaunched its in-person continuing-education program. Roll up your sleeves for interactive courses in subjects including jewelry making, furniture building, and woodworking, and you’ll be reveling in “I made that” vibes in no time.

Get Your Culture On

Fancy yourself a history buff? Celebrate your independence with a stroll through the newly reimagined Concord Museum, where you’ll discover exhibits on the nation’s own quest for freedom. The museum, which reopened in September after wrapping a $16 million renovation, doesn’t just cover the Revolutionary War, though; throughout its 10 new gallery spaces, you’ll find fascinating displays on everything from the Colonial town’s Indigenous tribes to key players in 19th-century abolitionist movements.

Don Your Chef’s Hat

Forget dinner for two. Cooking for yourself can be just as rewarding—especially after you’ve built up some culinary chops. At Christopher Kimball’s Milk Street Cooking School, you can choose from dozens of livestream classes and workshops, each taught by seasoned chefs who’ll answer your questions in real time. Whether you want to bone up on sushi rolling, finally nail that tofu dish, or perfect your chocolate cake recipe, your taste buds are in for a treat.

Take a Hike

You know who was really good at spending time alone? Henry David Thoreau. Make like the poet—and tap into your outdoorsy side—with a hike at Walden Pond, where Thoreau famously spent two years living, writing, and meditating in the surrounding woods. Offering a series of easy-to-navigate (and largely waterfront) paths and trails, the historical hideaway is the perfect place to peep towering pine trees and visitor-made stone cairns while you bask in sweet solitude.
—Andrea Timpano

Photo by Peter Brinch

Date Night Confessions

As told to A.V.

Dr. Stephen DeVincent and Rufus Gifford
Faculty Fellow at Tufts University’s Center for Animals and Public Policy and the U.S. Chief of Protocol, respectively

We really don’t have a date-night routine, but when we are at our Nantucket home, we like to have dinner at the Nautilus, which is our favorite restaurant. It’s casual, and they have great cocktails and fantastic food. It’s hard to get in during the summer because it’s so popular, so we often go in the off-season. Plus, we both drink bourbon in the winter and the Nautilus makes a good Old Fashioned. They also have a dish there—the whole roasted duck, which is served with steamed buns. Of all the restaurants we go to, if we had to choose one favorite dish, that would be the one. Then, after dinner sometimes, we’ll have a drink at the bar at Greydon House, an inn in the center of town. The interiors are very well done, and they have a beautiful bar area. We’re very low-key.

Craft the Ultimate Online Dating Profile

The dos and don’ts to sending the right message.

Be Honest

Sharing personal info with strangers, especially online, is scary. But if you’re after an authentic and meaningful relationship, says Dr. Monica O’Neal, a Harvard-trained psychologist and relationship expert, you’ll need to dish—at least a little. “Give your real name, height, and age, and be clear about who you are,” she advises, adding that you’re more likely to attract an equally honest mate that way.

Ditch the Sarcasm

“Sometimes people want to be cheeky and sarcastic, which can read badly and make you look kind of embittered,” O’Neal says. Instead, focus on using positive language. “Own who you are in a way that’s loving and confident,” she says.

Set Expectations

Whether you’re searching for a casual fling, a serious commitment, or something in between, it’s important to be upfront about what—and who—you want. “Put that in there,” the expert suggests. “If you’re a person who’s affectionate,” for instance, “then you should say something like, ‘I’m looking for someone who likes affection or who isn’t scared of PDA,’” O’Neal says.

Choose Photos Wisely

Superficial as it seems, profile photos matter—a lot. “The ideal number of photos is five or six, with three being the absolute minimum,” the psychologist says. Smile for the camera, include action shots that show off your social side, and—remember—don’t overdo it with selfies. “If somebody is only taking selfies, it would make me feel concerned about their self-confidence or what they’re not showing me,” O’Neal explains. —A.T.