Will COVID-19 Change Boston’s Dating Scene for Good?

Illustration by Jon Reinfurt

Way back in time, when people still went out to bars with strangers and you could touch your face in public, I went on a first date with a guy named Joe. We had agreed to meet at a bar he’d picked that was between our houses, and he texted as I was parking to let me know he’d gotten there early to snag us seats—a sweet but probably unnecessary gesture. The place, which looked like a Masonic hall with microbrews, was almost empty when I walked in. He was easy to spot: Sitting at the bar, tall and tattooed in a bright-blue button-up shirt, he was the only one who didn’t look like a dad. I crawled up onto the tall chair next to him, my feet dangling. Excited as I was, I was also prepared for almost anything—I’d done enough dating in Boston to know that it’s like Russian roulette, only with more bullets and without the mercy of a quick ending if it doesn’t go your way. I smiled and said, “Hey.”

I was here because one sleepless night a few weeks earlier, I had decided to pass the time deleting apps on my phone, but when I got to Tinder, I lingered and wondered if I should try it again before declaring it useless for the umpteenth time. I clicked it open and, a few swipes in, found Joe. In the days that followed, we texted a lot, which I took as a sign that he was either desperate or cool. (It can really break either way.) I learned that he always needs to be doing something, which is one of the reasons why he devours books. I also found out that goats are his favorite animal and that he hikes a lot, has watched Twin Peaks more than twice, likes to drink Negronis—which I find both disgusting and respectable—and uses words like “neat” unironically. All of this seemed promising.

Meeting him in person, I decided he was definitely cool. He said hello like we already knew each other and made small talk that didn’t feel like he was trying to fill space. He asked good questions, slid into stories that weren’t disguises for humblebrags, was an attentive listener, and even looked like he probably flossed sometimes. (Yes, the bar is low.) He told me about his job as a wine sommelier and was able to talk about it in a way that wasn’t pretentious. I told him about my job as a social media manager (a.k.a. professional tweeter), and he seemed to find that genuinely interesting. On most outings, by the end of my first beer I’ve typically bookmarked something problematic my date has said and considered leaving. But that didn’t happen this time. I let him order my second drink for me and we kept talking. All of which is to say, Joe was a truly exceptional first date—he was nice, funny, and didn’t say anything that made me immediately want to flee. He was that rare person who lives up to being what we think of as “pretty normal,” but whom I can almost never actually seem to find. It was practically jarring.

The novelty of this was so strong, I couldn’t help but ask half-jokingly, “As a cool wine guy, is this a normal date for you? Do you usually have luck on Tinder?” He smiled and answered me straight. Like me, he said, he’d downloaded dating apps during spurts of boredom. Not all of his dates were horrendous—some were even good and led to relationships—but like everybody else, he often found himself exhausted by the crucible of the modern dating world: cringey first conversations online, cringier attempts to start conversations in real life, getting ghosted, gaslighting yourself every step of the way—all standard stuff. For both of us, this date was the exception. We talked about this until the bar closed, swapping stories about bad dates and making fun of how Boston archetypes are often all too real. In a city full of all kinds of people, we wondered, why is finding someone to date so hard?

Looking back across the social chasm riven by the coronavirus, some of these complaints feel silly and quaint—having a stranger hug you, for one, is now cringey for drastically different reasons. But the core questions seem as relevant now as ever: Is there something about this city’s culture that makes dating here particularly hard? And now that social distancing has all but wiped out the dating scene as we once knew it, is there any hope that what comes next will be any better?

On the face of it, there’s no obvious reason why dating in Boston should be bad. We live in a small, tight-knit city that has a reputation for being full of smart people who come from all over the world to work in a bevy of industries. There’s even a compelling data argument: According to the U.S. Census Bureau, as of 2018 nearly two-thirds of Boston residents were unmarried. The home-rental app Zumper, meanwhile, ranked the Boston/Cambridge area as the second-best city for singles in the country—a calculation it made using the number of bars, restaurants, and singles in the area; access to dating apps; and average rental prices, among other data points. (Admittedly, some of those factors are less relevant now.) Yet if you’ve tried dating here, it probably feels like those numbers aren’t adding up.

It didn’t take much digging to confirm that I’m far from the only one who thinks dating in Boston is a nightmare. (I’m not sure if that’s good news or bad news for me.) Local therapist Brie Shelly says that many of her clients feel it’s hard to meet people here, period, let alone people they want to date. “If you come here for college, you’re already set up to make friends,” she says. “But if you’re in your late twenties to thirties, it’s a whole different ballpark.” After all, Massachusetts is known for a lot of things—being smart, having a weirdly intense sports culture, clam chowder—but friendliness isn’t exactly one of them. The Boston cold shoulder certainly isn’t the only thing that makes dating here tough, but it might be the most pervasive problem—in fact, suffering from it seems like a rite of passage.

Even when you do break through and meet someone, it can be hard to make more than a casual connection in such a cerebral city. Shamika Rucker, a personal trainer in her forties, first moved to the area for a job at Raytheon and spent a dozen years on the road as part of her role there. She’s met people in different cities, towns, and countries, and says with confidence that there’s something about Boston that makes connecting with others a lot harder than it needs to be. “I think that a lot of people here are introverted, focused, and regimented in their lives,” says Rucker, who has found the local dating scene to be such a letdown that she even considered moving at one point. “There are a lot of intellectuals and people who have great careers and focus on that—it makes it easier for them to remain introverted.” Maybe so, but Boston is hardly the only city with a high-achieving work culture, so what gives?

Until recently, at least, one difference might have been that while cities such as New York and San Francisco like to work hard and play hard, our motto has long been closer to work hard, sleep hard. Despite attempts to redefine our drowsy, bookish city, the late-night culture here is basically getting beers with your coworker who also stayed at the office way too long. We tend to go out for drinks to decompress or to network—not necessarily to meet new people. Even if you do want to hit the town, unless you’re trying to crush PBRs with college students or order bottle service at the Grand with finance bros, the options are pretty slim.

Limited access to singles who are ready to mingle is only part of the problem, Shelly argues: Successful dating also has to do with how you act once you’re on a date. Maybe it’s because Boston always feels like a small town—it didn’t take long for Joe and me to realize that we had friends in common—or because so many people are focused on their careers, but there seems to be an abundance of caution about opening up here that makes laying the foundation for a successful relationship particularly difficult. “How motivated you are to actually engage with a person ultimately has a lot to do with vulnerability,” Shelly says—which doesn’t bode well for Bostonians, who collectively tend to be proud but also very guarded.

That critique resonates with Corinne Wardian, a frustrated thirtysomething who says that five years of dating in Boston has taken a toll. Originally a Midwesterner, she says exploring the city is one of the main ways she spends her free time, which means she’s often meeting new people. When she goes on a few dates with someone, she finds she’ll get up to that point of vulnerability—only to have the other person fall off the face of the earth. “You get tired of your friends being like, ‘You’re awesome!’ And you’re like, ‘Am I? Because it’s not adding up right now.’ Is dating here bad or am I bad at it? is a question I ask myself all the time.” She has started to wonder how much longer she’s willing to put up with it. “I don’t necessarily have a timeline or checklist—I’m not like, ‘I need to be married by X date,’” she says. But she does want to feel like she has a chance at a future with someone, and she’s tired of staring down dead ends.

Another problem might be that dating simply isn’t a priority for many Bostonians—in part because they don’t necessarily plan to stick around. Ben (who for professional reasons would rather not share his last name), a MassArt graduate in his twenties who’s also lived here for five years, says he finds it hard to get serious with people when he’s never really sure how long he or his dates might be here. “People do use Boston as a revolving door—at college and then out of college as a starter city. I’ve definitely used that term before when talking about my relationship to Boston,” he says. He may be onto something: Greater Boston is the 10th-most-populous metropolitan area in the nation, yet Massachusetts is among the top five states that people leave each year. And while we often think of students as undergrads, a big chunk of the 250,000 students here are in grad school, often in their twenties and thirties but with similar plans to leave.

As you read this, of course, the COVID-19 outbreak has upended pretty much every aspect of our lives, dating included. Moments of crisis often bring new perspectives and force us to refocus our priorities. The marathon bombings brought us together and showed how Bostonians could act as one when the moment demanded it—after all, we sheltered in place without question at the time simply because the governor asked us to. When social distancing first brought Boston to a screeching halt, many of us reconnected with people we hadn’t talked to in a while. Did we find ourselves looking for love in a new way, too?

The wave of outreach in the early days of the coronavirus—from friends, from people I hadn’t heard from in years—made me wonder if there is hope of a better dating world in Boston hovering just below the surface of the regular, less-than-inspiring one that everyone is trying to muddle through. People seemed to be starving for intimacy—and sure enough, it didn’t take long for them to find new ways to connect, even when public health officials were warning us to stay at least six feet apart. Some have taken to trying first dates over Zoom—you can even Venmo your companion cash for the bottle of wine they bought, if you’re feeling chivalrous. Others returned to a more tried-and-true approach: People have reported hearing from exes, which I guess might be evidence that there’s always time to reconsider (and that there’s nothing like a crisis to make you miss what you had). But we’re all in a grand experiment here, and it’s hard to know where it will go. Being forced to make the extra effort to connect, at the very least, might mean that we’re all a bit more willing to put ourselves out there to try to create real relationships.

In talking with her clients in recent weeks, Shelly said she’s found that a lot of people have made a quick pivot to virtual dates via video chats, with drastically varying results. “It’s been interesting to see some people are fine with [social distancing] and then some people are devastated,” she says. The people who are devastated are realizing how much they took for granted: It’s a real wakeup call to see the stark difference between a Boston in which it is difficult to meet people and a Boston in which you’re literally told you can’t. Still, she points out that this shakeup of norms could be a good thing, leading to a “deeper appreciation of other people” or even an opportunity to pause and focus inward for a time.

When I reached back out to Ben to see if he felt differently about looking for someone given the new reality, he was still figuring it out. “I think people’s perspectives will change,” he said. Specifically, he wondered whether the pandemic will have a profound psychological effect on single people who are suddenly faced with the stark reality of what it means to be alone in a time like this. Before social distancing, when we first spoke, he had hoped to find a mate merely by going about his life. “I like to believe that if I put myself in the situations that I love in the places that I love with the people that I love platonically, then I’ll meet someone,” he told me at the time. But now that our lives are specifically structured around not meeting people in an effort to stay healthy, he recognizes he’ll need to find a new plan. After all, we all have to get out of our comfort zones and find fresh ways to get close emotionally when we’re not supposed to be close physically.

In some ways, maybe it’s easier to build new habits when everything around you is changing. During this crisis, I’ve often thought back to advice that Shelly offered about what to do if you want to move a relationship forward: reach out, open up, and don’t be afraid to show who you really are.

Of course, when Joe and I were sitting at the bar mulling whether there was a hack to dating in Boston, we never could have seen the pandemic coming, but we did cover some ground that feels relevant now. He told me how he used to want to be a writer but had to drop out of school because he had cancer, and about trying to rebuild his life afterward—he answered almost any question I asked. I told him about living in New York, confided about a friend’s tragic accident, and unraveled how I ended up back in Boston, where I’d grown up. It wasn’t a therapy session, and it wasn’t all dark. It was just one of the least inhibited first conversations I’ve had with a person in Boston—and that’s a shame. The funny thing about vulnerability, though, is that it can catch on. After all, if you see someone else open the door, it feels safer to enter. And right now, we could use a little more of that openness. Instead of waiting for someone or something else to show us the way, maybe we should just start with ourselves. After all, at this point, what’s the worst that could possibly happen?