Ask A D.C. Native: How can dating here suck less?

D.C. singles feel hopeless about dating here that one social media user claimed it’s more likely for the rats to find love in the city than you. Based on my dating experiences, I’m inclined to agree, but hope persists. It’s my nature.

Perhaps it’s the accumulation of stories I consumed while reading the Washington Post’s On Love column. Every Sunday, it profiled Washington-area couples, tracing their unexpected paths to the altar. Week after week, it reminded me that romance was happening all around me, even when I wasn’t sure it would happen to me.

The city hasn’t stopped producing love stories. And yet, the path to finding it feels elusive. Beneath the rose-colored tint of those Sunday profiles lies a harder truth: building lasting connection takes work. 

Getting the ball rolling, though? That used to feel easy. In high school and college, connecting with a new person was simple: if I saw someone who piqued my interest, I looked at them, they looked at me, we had a brief conversation, and phone numbers were exchanged. 

This was before technology ruled our lives, and there was no guarantee you’d ever see that person again. So if you had a moment, you took advantage. It didn’t matter where you were: waiting for a train at Metro Center, the food court at PG Plaza mall, on the sidelines at the basketball court, or at Six Flags with friends. 

When social media entered the scene, some rules of engagement changed but it was still pretty straightforward. With a widened pool of people on sites like BlackPlanet and MySpace, I’d scroll through someone’s profile page, send a message if I liked what I saw, and lit up when they responded.

From there, connection unfolded naturally. You might chat incessantly online, spend hours on the phone talking about everything under the sun, meet up and canoodle on the stoop, or just wander around the city (my favorite pastime). Maybe our first date would be watching a movie at Union Station, then going to McDonald’s for a five-piece nugget meal. Or if you had a little coin, you might meet up at ESPN Zone downtown to play games and split fries. The approach was light. The stakes were low.

Then I became a twenty-something in the mid-2010s, navigating peak D.C. clubbing years when places like Dream, Glow, Marvin’s, and Patty Boom Boom became stages for meeting people. Meanwhile, happy hours, day parties, and networking events offered their own social rituals.

But somewhere along the way, as I moved into adulthood, interactions with new people began to feel more transactional. Networking often began with the familiar, “So, what do you do?”, and that question eventually seeped into the dating scene.

Before you’ve fully introduced yourself, someone may already be assessing your profession, your affiliations, your access, or your usefulness. What you do for work becomes shorthand for who you are and, sometimes, whether you’re worth getting to know.

Beyond this classic opener, D.C. singles seem to have an endless list of grievances about dating here: Is six degrees of separation actually a problem? What if my current boo used to date someone I know? Do I really want to date someone that lives across the Potomac River? And then there’s the big one: how do we move from “just vibing” to being intentional?

These are valid concerns, but they don’t quite get to the crux of the matter: How do you stay open to connection without losing yourself or letting the search wear you down? 

Erika Ettin, founder of the online dating agency A Little Nudge, says singles in D.C. could use a mindset shift. “If you believe that D.C. is a terrible place for dating, that will become your reality,” says Ettin, who isn’t dismissing anyone’s bad experiences. Instead, she’s questioning what happens when frustration becomes a substitute for participation. 

“A lot of people know each other in D.C. And D.C. can also be quite transient, which can feel frustrating. But those issues can exist anywhere. I believe if you lined up 20 people who live in different places and asked them, ‘How is dating in your city?’ they will all say, ‘Awful.’ Complaining requires less energy than trying something new.”

Psychotherapist Alexis Logan of the D.C. based Center for Intimacy and Relationships also encourages people to start with themselves. “Define what connection is. Define what intimacy is. Define what you’re looking for,” she says. Then, you can relay your needs to a potential partner. “Give them the opportunity to choose for themselves by being clear about what those things mean for you.”

Logan also encourages singles to establish boundaries by asking themselves what they’re willing to tolerate, what they can offer, and what they don’t have room for.

Once you’re mentally prepared, Ettin has a pretty straightforward dating prescription: attend three social events a month — one explicitly dating-oriented, and two where you can simply “say hi to a new person.” The goal isn’t to turn your social life into a performance metric. It’s to increase your opportunities for connection.

The same applies online. Ettin recommends using dating apps deliberately rather than compulsively: limited time, active messaging, and no endless swiping. 

And most importantly, she says, you should detach yourself from the outcome. A date doesn’t have to become a relationship to have been worthwhile. Maybe you discover a restaurant, learn a new game, or have a great conversation. Maybe you see the person twice and realize that’s enough. “It means that’s all it was supposed to be,” she says.   

Jessica Lewis, founder of Play Play DC, focuses on a grayer area of dating: the space between meeting someone and deciding what, if anything, they’ll become to you. For Lewis, that in-between space is ripe for curiosity. As a kindergarten teacher, she observed that play is “our most natural state.” Her social club offers alternatives to nightlife dating in D.C., like the popular Indoor Recess, with play stations designed to indulge childhood fantasies and old-school gym jams that channel the carefree spirit of a high school dance.

Personally, this is my favorite approach. Having an open and playful spirit lets me effortlessly explore my interests and curiosities with a companion. Sometimes it even leaves me breathless. For instance, a chance encounter at Malcolm X Park once turned into a four-hour conversation about art and travel, followed by an impromptu dinner at The Grill from Ipanema and a game of chess over gelato at Pitango.

While that relationship didn’t work out, it wasn’t a loss for me. Being playful is still a gift.“It gives you permission to explore yourself,” says Lewis. 

That practice also requires grace. People are imperfect. They don’t always get it right. They may need feedback, boundaries, or simply the opportunity to adjust. Dating can become disposable when we expect other people to arrive already fully formed. 

Then, we have to figure out how to move from play to intention without killing the vibes. Rather than asking yourself, Is this my person? on the first date, Logan suggests smaller, more immediate questions that are still impactful: Do I like this person? Do they interest me? Do I leave feeling energized or drained? It’s a different kind of vetting, one that prioritizes curiosity over judgment but still chips away at what’s most important to you. 

Perhaps the real challenge of dating in D.C. is practicing the skills that make connection possible in the first place: courage, curiosity, and playfulness. Did teenage dating offer us something we’ve forgotten as adults?