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The Ultimate Guide on How to Date in DC

What’s going on with dating in Washington? Here’s our guide to offline romance in the region, from places to meet and sweet success stories to dating disasters and what bartenders really think when they spot a potential couple.

Written by Damare Baker
, Daniella Byck
, Kate Corliss
and Kim Habicht
| Photographed by Lauren Pusateri | Published on May 8, 2025
Tweet Share

The Ultimate Guide on How to Date in DC

What’s going on with dating in Washington? Here’s our guide to offline romance in the region, from places to meet and sweet success stories to dating disasters and what bartenders really think when they spot a potential couple.

Written by Damare Baker
, Daniella Byck
, Kate Corliss
and Kim Habicht
| Photographed by Lauren Pusateri | Published on May 8, 2025
Tweet Share
Contents
  1. So, Where Do I Start?
  2. Joan Vassos
  3. Meet-Cutes
  4. Bartenders Spill
  5. First Impressions
  6. Dating Disasters
  7. Match Game
  8. Derek Sherman
  9. Meet and Greet
  10. You’ve Got Mail
  11. Marissa George
Y

ou’re trying to find love in DC. How hard can it be, right?

Pretty tough, actually.

Dating apps, once applauded for their choice and convenience, have become a swamp of their own, turning romance into a digital hellscape of prompts, swiping, and meandering conversations that often don’t lead to actual dates. According to a 2023 Pew report, 46 percent of respondents said they had a somewhat negative experience with online dating platforms—and remember, dating is supposed to be enjoyable. Another 2023 survey, by Axios and the Generation Lab, found that 79 percent of college students surveyed were barely going on the apps at all.

Dating pros who work with singles in both online and offline spaces are seeing the fatigue. “People are so exhausted from online dating—they’re exhausted or disillusioned,” says Michelle Jacoby, the matchmaker and dating coach behind DC Matchmaking. “Dating has become a little crazy with all of this access to people, but people not really connecting.” Paywalls that require users to cough up cash to see their “best” matches, the blurring carousel of faces, the invention of new terms to label flaky behavior, such as breadcrumbing and orbiting—it can feel like we’ve collectively swiped left on the art of courtship itself.

In response, there’s a yearning to return to a time when you could meet a potential partner standing in line for coffee or having a flirty encounter at a party. Shifting your love life from the online to the offline world isn’t impossible in 2025. We’ve compiled a guide to dating without the apps, including where to meet people (whether in the wild or at designated dating events) and how to overcome some of the challenges Washingtonians face in the dating ecosystem. Plus, you’ll find inspiration in stories of successful meet-cutes—or solace that it really can be worse, in our cringe-worthy dating disasters.

 

So, Where Do I Start?

If you’re looking to meet someone off your phone, consider these three recommendations. The number-one tip: Don’t stress about the outcome.

Photograph by Getty Images.

Where Like-Minded People Gather

The easiest way to meet someone you may click with? Use hobbies as a starting point, says dating coach Michelle Jacoby of DC Matchmaking. Dating apps provide limited space to express your interests, which can make it hard to gauge whether you have much in common beyond photos or prompts about “simple pleasures.” But if you hit the bouldering gym or a painting class because it’s something you actually like, you’ll know you’re already surrounded by kindred spirits—and have a good time, regardless of who you meet.

“I have been encouraging my clients to go to Meetup groups,” says Jacoby. “Be in the moment and just have fun.”

Active types can join recreational groups, from DC Bike Party to hiking clubs that explore Shenandoah National Park. Book clubs at shops such as Lost City Bookstore in Adams Morgan and Solid State Books on H Street are great places to find fellow bibliophiles, and discussions on the latest read can turn into deeper conversations. A bonus: You’ll likely encounter the same faces repeatedly.

Places That Lend Themselves to a Natural Approach

Not every spot is going to be ideal for sparking conversation. (Think silent libraries or thumping nightclubs.) Seek out places with openings for easy introductions and the right environment to continue chatting. For example, Washington has a vibrant social-dancing scene, including Thursday salsa socials at La Cosecha at Union Market, blues dancing at Maryland’s Glen Echo Park, and weekly swing sessions at Josephine Butler Parks Center near DC’s Meridian Hill Park. You don’t need to bring a dance partner, which means you’ll meet people as you pair off throughout the evening.

Or, if you’ve got a dog, consider it your wingman: Start frequenting a local dog park or canine-friendly bars such as Dog Daze Social Club in Logan Circle, where pups are a natural opener for owners, who already have something in common. And while recreational sports leagues may feel like a DC cliché, Jacoby puts them at the top of her list of locales for meeting potential partners. They’re intended to be social, with designated opportunities to mingle before or after games in groups such as Stonewall Kickball League or at a Dill Dinkers’ Open Play pickleball clinic. Even a bar with billiards—Nice & Easy in NoMa or Carpool in Arlington—can provide a chance to engage with new people.

Anywhere, Really

Opportunities to meet someone special can be found virtually everywhere, but many people remain absorbed in their own world, wearing earbuds and rushing from place to place. “The pandemic made us even more introverted, and people are really longing for that personal connection, which is ironic because they’re looking down at their phones,” says Jacoby. “Talk to people and look up, and don’t bring your phone—turn it off.” A simple compliment or amiable remark can spark a conversation. Jacoby’s advice: “Treat every stranger like a friend.”

Of course, there are concerns about appearing creepy or overstepping, especially for men. Context matters, cautions men’s dating coach Erika Davian. Approaching someone in a vulnerable setting—a gym, a doctor’s office, during yoga—can come off as intrusive rather than charming. The key is genuine curiosity, not an agenda, she says. If you’re trying to “get something” (say, a number or a date), the interaction can feel transactional.

In a work-driven city such as ours, Jacoby recommends leaving that networking mindset at the office. Approach interactions with openness, not interrogation. “People are too focused on qualifying the buyer,” she says. “Stay open and just enjoy meeting new people.” Everyday moments such as waiting for coffee or commuting on the Metro can lead to unexpected connections—if you’re open to it. (Don’t believe us? Scroll down for stories of real-life meet-cutes.)

 

Reality Check

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Joan Vassos

The Golden Bachelorette

The 62-year-old Rockville resident found love while dating a group of senior singles as TV’s first-ever Golden Bachelorette. Here, she answers some of our dating questions.

Do you have a local first-datespot you recommend?

I did usually go in Bethesda because it’s central to a lot of people if they’re from DC or Virginia. I’d go to Woodmont Grill, I’d go to Black’s [Bar & Kitchen], I love Mon Ami Gabi. They all have nice bars, great atmosphere. Those three places were always good.

How is dating on The Golden Bachelorette different from dating at home?

Dating, not just in Maryland but in general, at this age is hard. I did a dating website. I didn’t love that–it felt like a job. You had to spend a lot of time texting strangers and trying to figure out if their profile was truthful, which I found out a lot of times wasn’t. Dating on national TV–though that in itself is weird–the guys are vetted for you.

What advice do you have for DC-area singles?

I had a tendency to go for the bad boys or people that are just epic­ally fun, but when you’re thinking about what you want your life to look like, find the person who fits those categories. Concentrate and aim for what you want your long-term person to be.

 

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Meet-Cutes

Sometimes, that fairytale meeting really does happen. Here are five sweet stories of real-life romantic encounters.

Next Stop: Love

“We were both living in Virginia at the time, and we’d take the Yellow Line into DC every day. We rode in the same car and got off at the same stop, but we’d exit in different directions. During my commute, I would text my friends about my ‘Metro crush.’ I would listen to ‘Crush’ by David Archuleta. And this was in 2022, so everybody was wearing masks—at this point, I hadn’t even seen his whole face. I remember texting my friends the day the mandate was lifted, to let them know he was still hot without the mask! I never thought anything was going to happen. We never talked until one day about four months into riding together. We got off at our usual stop and went our separate ways, but suddenly I felt a tap on my shoulder. It was him. He said, ‘Hey, I’m moving into the city, so this is my last day on this Metro line,’ and he asked for my number. The whole time I was texting my friends about him, he was going into work and telling his coworkers about me. They actually helped him game out how to approach me. When he proposed, he had the ring box embossed with a map of the Metro. To this day, he’s in my phone as ‘Metro Crush.’ ”

—Brooke, 31, librarian

 


 Cupid’s Claw

“Both of us worked at José Andrés restaurants: I was a prep cook at Minibar, and my now-husband, Simon, was a sous chef at China Chilcano next door. At Minibar, we got shipments of whole lobster, but we only cooked the tails. It was my job to drop the claws off at China Chilcano every day, which was how I got to know the staff over there. I honestly never noticed Simon at first, but he noticed me right away—he tells me now, a decade later, ‘You had the butt.’ ”

—Rochelle, 34, pastry chef

 


Silver Lining

“I’m originally from Tennessee, and I had moved to DC for a job. I made some friends in my apartment building, and I got invited to go to a Nats game. I’m not a big baseball person—when I saw Nats hats, I thought it was a Walgreens logo. So I went, and we’re not even halfway through and it started pouring down rain. Somebody suggested going to Salt Line across the street and grabbing a drink, until we figured out how long the rain delay would last. They have an outdoor bar with an [overhang], so you can run underneath. There was a little space open, and I said, ‘Are ya’ll in line?’ And my now-husband said, ‘You’re not from here—you said ya’ll.’ We started talking, and he asked for my number. I normally wouldn’t do that, but I was like, ‘Sure, why not?’ People said, ‘Oh, you’re not going to meet a husband in DC.’ I pushed it out of my mind, and it ended up working out really well for me. It just seemed like fate.”

—Meg, 34, attorney

 


Rats Amore

“I met up with some guys at my friend’s place in Logan Circle for a boys’ night. We had just started on the walk from his rowhouse to Dupont when we ran into his neighbors outside in their backyard. Turns out they were throwing a birthday party for one of their roommates. My friend got to chatting with them about their mutual rat infestations—they lived in the same row of houses, after all—and they invited us inside to check out the holes the rats were using to sneak into their place. I had been expecting to go out to the bars rather than crashing a stranger’s birthday party, so I was feeling a little out of place, but I grabbed a beer and hung out in the kitchen. That’s when Alex, the birthday girl, came over and introduced herself. I had noticed a bunch of cow decor all over the house, so I asked her about it—she really loves cows, which was a great entry for me because my family owns a farm. After the party wrapped up, she invited me to Shenanigan’s with her and her friends. We danced, got Jumbo Slice, she asked for my number, and I walked the whole way home from Adams Morgan to the Waterfront.”

—David, 26, government worker

 


Art and Heart

“I was going to the National Gallery of Art, just as a single date with myself. I was walking around the Impressionist gallery, and I saw this woman standing in front of this big painting by Mary Cassatt. She was tall and had bright-blue eyes, very beautiful. The painting she happened to be standing in front of was a painting I actually wrote a report on—I was attending American University. She appeared to be alone, so that gave me the confidence to go up to her. I asked, ‘Do you like the painting?’ She said, ‘Yeah, it’s so beautiful.’ Then I went, ‘It’s my favorite in the gallery. I wrote a report on it for school.’ She took me over to this giant painting of Napoleon because she’s a European-history nerd. She was explaining that she had written a report on Napoleon for school. I asked, ‘Do you want to walk around the other galleries together?’ We went from room to room and talked about history and art and our degrees. We probably hung out for a couple of hours. Today is actually our two-year anniversary.”

—Claire, 22, conservationist

 


Related
50 Great Date Ideas in DC

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Bartenders Spill

Yes, they can spot a first date from a mile away. Here, mixologists share how they sense if it’s love at first sight or a dating disaster before you can say, “Check, please!”

First Dates

“You can tell everyone’s on their best behavior. Spine straight, using napkins, delicately drinking,” says Beth Lindsay, who has witnessed hundreds of first encounters as the owner of Board Room, a 12-year-old board-game bar in Dupont Circle. “And then when the date gets up and goes to the bathroom, they gulp their drink down and look at their phone to text.”

Meanwhile, David Strauss, owner of the Mount Pleasant speakeasy OKPB who has spent nearly three decades in the restaurant industry, has observed that first-daters will often order fewer drinks (to avoid inebriation) but stay longer. “Which is by no means a complaint,” he hastens to add. “We love watching from the outside and seeing how things play out. Ninety-nine percent of the time when you walk in, the bar staff is rooting for you to work out.”

Doomed Relationships

As anyone who’s played a heated round of Monopoly or Catan knows, board games can reveal some unsavory aspects of participants’ personalities. The Board Room’s Beth Lindsay describes a couple who came in to play Battleship. “He was really into it,” she says. “The young lady left to use the restroom, and he took a picture of her board. Later on, he used the restroom and I [told her], ‘Just letting you know, that guy’s cheating.’ ” Because some games take only a few minutes to complete, Lindsay sees a lot of serial daters: “My personal record is a gentleman I saw come in three times on a Saturday with different dates.”

Sometimes, it’s not what people do but what they say. Shelly Caviness, manager of Morris American Bar in Mount Vernon Square, recalls a red-flag moment: “I overheard a girl say, ‘I talked to my mom about you,’ and the guy said, ‘Yeah, I think it’s too soon for any of that.’ They split the bill afterwards.” If a meetup isn’t going well, she says she’ll get that look, and she has no problem asking someone to leave if they make their date uneasy. “We’re always checking to make sure you are safe and having a good time. If you’re feeling uncomfortable, please tell one of us.”

True Love

Believe it or not, servers want your Hinge date to turn out to be a soul connection almost as fervently as you do. “As much as we love cocktails, we really do love hospitality and relationships,” says Strauss. Bartender Zoe Pipines recalls a man who was so nervous about his date that he came into the Dupont Circle Mediterranean restaurant Balos Estiatorio a day early to check out the menu. The next day, his blind date ended quicker than expected. He stayed to order food and struck up a conversation with a woman sitting near him. They chatted until close and are still dating months later. Pipines knows because they’ve come in for their “anniversary” each month.

Says Strauss: “We talk a lot about it as a group. Like, ‘Remember that couple that came in on Friday? They stayed for three more and left together.’ We love seeing that. We get a front-row seat to the best cross section of humanity every night.”


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First Impressions

So you’ve met someone and it’s time to schedule a first date. Finding the perfect spot can be a balancing act, especially as you’re just getting to know each other. Here are nine destinations to consider, depending on your first-date vibe.

Photograph courtesy of Barca.

If you want a bar with reservations, to avoid awkward waits:

Barca in Old Town for wine by the waterfront; The Pub & the People in Bloomingdale for drinks and snacks in a cozy tavern; or Service Bar on U Street for cocktails and mocktails in a casual space.

Photograph by Hawkeye Johnson Photography.

If you want a nice daytime cafe with ample seating:

Yellow in Union Market for creative coffee drinks and pastries; Gustave in Del Ray for French baked goods in a sunny beer garden; or Ellē in Mount Pleasant for lattes at a table for two.

Photograph by Getty Images.

If you want an active date where you can easily chat:

Perch Putt in Tysons for mini-golf with a tiki bar; the United States Botanic Garden for a floral stroll and (if it’s going well) an easy transition to more museums; or Pinstripes in North Bethesda for bowling in sleek lanes with a full menu.

 

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Dating Disasters

Not every date is going to be a dream, but some are worse than others. Here are six stories of meetups gone wrong.


Pop Quiz

“I was still learning my buses and trains, so I texted to say, ‘Hey, I’m running late.’ Minutes later, I get this text that says, ‘If you can believe it, this girl does not care about me, she’s literally going to be 25 minutes late, this bitch.’ I was like, ‘I think you texted the wrong person.’ When I arrived at Church Hall, he had one of those huge tankards of beer, something that looks out of medieval times. And he’s already been drinking it. He goes, ‘I actually started looking you up while I was sitting here. I just want you to know that you answered this question on Quora about how you lost your virginity, so you should probably scrub it from the internet.’ I went back later and scrubbed it, of course, and to find that, you had to go through five pages of Google. He said, ‘Because you’re so late, I’m not going to buy you a drink unless you can answer these different questions.’ Then he quizzed me on something to do with European history, but he was really upset that I actually got the questions right. The bartender slipped me a note on a napkin when the guy went to the bathroom: Hey, do you need help? I looked up at him and said, ‘Honestly, this is hilarious. I just want to see how it can get worse.’ ”

—Franny, 27, project manager

 


Hide and Seek

“I met this guy for a date at the Georgetown waterfront. We were walking along the path that runs along the park when suddenly, without saying anything, he started running. I was really concerned—I thought he must have seen a bee or was having a panic attack. Then he went and hid behind a tree. I went over and asked if he was okay, to which he replied, ‘Oh, my God—I just saw my parents and they weren’t supposed to be here.’ I totally under­stand that’s an awkward situation, but he was almost 30. The rest of the date lasted no longer than ten minutes.”

—Maddie, 29, consultant

 


Deal Breaker

“She seemed fun, a little on the wild side—a break from the attorney lifestyle. This was during the pandemic. [Her friend] had been doing some comedy clubs and booked a gig somewhere in a farmland area where they could have an outdoor event. The day before, she brings up, ‘So listen, I do owe some money to a coke dealer in DC. I promised to push a little product at the show to help pay them off. So don’t freak out if I’m going from table to table. That’s fine, right?’ There was a part of me that said, Well, this should not be a surprise to me at all, based on everything I know about this woman. She literally just disappeared for a few minutes, I tried not to look where she was going, and then she came back and said, ‘Oh, sorry, just had to take care of something’—very subtle. At the end of the night, I was like, That was a bridge too far for me.”

—David, 41, attorney

 


Cast Away

“The reason I wanted to go on a date with him was because he had a motorcycle. As soon as I saw him, I noticed he was wearing one of those removable casts. He told me he’d been in a motorcycle accident, so the motorcycle was destroyed and now I could never ride it. He proceeded to take off the cast and put it on the table in front of me! It absolutely reeked of BO—I was disgusted. The whole time, the stink from this cast is wafting up at me.”

—Ruth, 26, public-relations rep

 


Train to Nowhere

“I was on a first date with this guy I felt I had a real connection with, and I’d mentioned I was doing some modeling work. He told me he’d actually just been part of a local PSA about pedestrian safety, which I thought was cool. The next day, I was on the Metro and I saw this PSA with a photo of him crossing a crosswalk! I texted him a picture of it. After several days, he hadn’t responded, so I was like, ‘Okay, now I just have to stare at this guy on my commute.’ The PSA was up for several months—on the Metro, on the sides of buses, on the Old Town Trolley, which I took to work every day. He ghosted me, but he was everywhere.”

—Kelly-Lynne, 36, content creator

 


Wife Guy

“People were still cautious about meeting up because of the pandemic, so a Hinge match and I decided to do our first date over FaceTime. Our text exchanges over that week had been very flirty, so I wore a lacy tank top that was basically lingerie. On the third ring, a woman answered his phone. I was shocked because he’d told me he was widowed and also because I was a quarter naked. She told me she was his wife and, in spite of what he’d told me, she was very much alive. Not only did she show me her ring—beautiful rock, by the way—but she happened to walk down her hallway, which I saw was lined with their wedding photos. She was super-nice and even told me she wasn’t angry with me. You could kind of just tell in her face that she just felt sorry for me.”

—Amber, 37, consultant

 


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Match Game

Singles everywhere like to say their city is a hard place to date in, but each location has its own challenges. Here, area matchmakers and dating coaches share some of the problems specific to Washington and how you can maneuver around them. Hint: It comes down to changing your mindset.

Challenge #1

Location Frustration

There’s some truth to the jokes about District residents not wanting to cross the river to Arlington and vice versa. But you may have to look even farther—we’re talking beyond the Beltway—for The One. Michelle Jacoby of DC Matchmaking encourages clients in the city to be open to the idea that their future partner could live in, say, Annapolis or Baltimore. One barrier? “Something that’s perhaps unique to DC is that a lot of people don’t have cars, especially women in their thirties,” says Jacoby. She’ll set up clients near Metro stops if they request it (and they do), but a Zipcar membership could be an investment in your love life that expands the pool of potential connections.

 

Challenge #2

Drawing Party Lines

DC is mostly blue, so perhaps it isn’t surprising party membership is a major concern for singles here. In particular, being MAGA is a red flag for many. “The number-one deal breaker we get is ‘a Donald Trump supporter,’ by far,” says Callie Harris, a senior matchmaker at Three Day Rule. Though it seems impossible to disentangle political ideologies from personal values, Ali Deckelbaum and Molly Dresner, cofounders of the Court, a local matchmaking service, encourage people to look beyond Democrat and Republican. “We try to get deep into your stance on specific issues, instead of just broad-stroke labels,” says Dresner. Matchmaker Natalie Fry of It’s Just Lunch Washington DC recommends avoiding politics on a first date: “Focusing on shared values and interests—that can transcend differences there. Someone who is living a life of purpose and meaning is really underlying that preference for the same political affiliation.”

 

Challenge #3

Dating a Résumé

All of the matchmakers we spoke with say app culture has impacted dating. Singles have become accustomed to filtering potential romances by somewhat meaningless metrics that encourage them to make swift judgments based on minimal information. “You’re forced to filter by things that don’t indicate compatibility,” says Harris. “We tend to think, ‘Oh, they’re asking me to filter by height, so that must mean it’s important.’ ” But in DC, experts say these snap judgments go well beyond the basics. “We have a ton of clients who are super-competitive and are into job titles and higher education, number of languages spoken, how many countries they have visited,” says Dresner. First, take a breath. Then consider what’s really important in a partnership: Is it a high-level security clearance and a passport filled with stamps? Or traits such as trustworthiness and empathy?

 

Challenge #4

Too Busy to Get Busy

According to the matchmakers, stereotypes about workaholic Washington manifest in dating. It’s hard for potential couples to gain momentum when dates are few and far between due to scheduling conflicts. Fry suggests adapting the same mindset you would in business: “Schedule dedicated time for dating, just like you would important work meetings.” Jacoby shares the story of a client she kept introducing to compatible matches, but his busy travel schedule for work kept any romance from blooming. However, when the pandemic hit, he was forced to stay put in Adams Morgan, and Jacoby connected him with a woman in Loudoun County: “He ended up getting married because he couldn’t go anywhere.”

 

Reality Check

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Derek Sherman

Married at First Sight

On the DC season of Married at First Sight, the 32-year-old met and married his now ex-wife at the altar. Currently living in Arlington, he shared his thoughts on love and dating.

What’s your dream date?

I’m a sucker for different activities. It would be going into DC, starting off at Whiskey Charlie, then going to Artechouse. Maybe checking out one of the museums on the way, then going to Swingers. My favorite dates have been at Christmastime, going to Enchant or towards Manassas to check out the Christmas-light shows.

What’s the number-one lesson you learned during Married at First Sight?

Honestly, one, patience, and two, being yourself. One of the hardest things from doing my show is trying to balance acting like you’re married and being yourself, and at the same time trying to impress them like a first date. The thing that helped me the most was just being true to myself, and again, patience and listening.

Do you have any advice for area singles?

Just getting out there! For singles in the DC area, one of the best things they have going for them is the diversity of what’s around you. We get pushed into our own bubbles, but just expanding those is the best advice. There’s so many different events happening. It’s a great way of having an icebreaker if it’s a new experience.

 

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Meet and Greet

One convenient aspect of dating apps? You know everyone is looking to meet someone. Dating events apply that same principle, just to the offline world. These days, you’re not limited to speed dating: Here’s the rundown on three events around DC.

Photograph of couple courtesy of The Feels DC.

Singles on Socials

languageWebsite

The vibe: Happy hour.

Age group: Some events are designated for the twenties crowd, while others cater to thirty- and fortysomethings.

Icebreaker: Question cards to spark conversation—think “What’s your favorite Italian restaurant?”

After spending all day on a computer screen at work, who wants to transition to a phone screen for dating? That’s the idea that inspired Sarah Goldenberg to create an after-hours alternative to apps. Women come to the space first, spending a half hour getting comfortable and acquainted with one another before men enter the venue. From there, it’s typically a low-pressure happy hour at a bar, though there have been one-off evenings at the Phillips Collection’s after-hours program or even a run club for a change of scenery. Attendance ranges from 60 to 250 people.

Price: $20 to $40.

 

The Feels

languageWebsite

The vibe: Intimate and a little woo-woo.

Age group: A wide swath from twenties to fifties.

Icebreaker: Facilitators share an embarrassing dating story.

Founder Allie Hoffman takes inspiration from psychologist Carl Jung and writer Joseph Campbell’s “hero’s journey” as well as her own experience with meditation and circlework. The event starts with drinks and mingling before settling in for an introduction and learning what type of body contact attendees may experience during the program. Then they’re split into rotating pairs to move through prompts that get under the surface. For example: What’s something you learned from your parents and something you’ve had to unlearn? Duos later reflect on each other’s responses, followed by a “somatic” element—a hug, extended eye contact—to be fully present in seeing how someone makes them feel.

Price: $83.

 

Cuffing Season

languageWebsite

The vibe: A night on the town.

Age group: Between 23 and 33.

Icebreaker: Bingo boards with squares such as “Find someone with a tattoo” for an excuse to approach someone.

Run by bar influencer Bruce Allen (@drinksinthedistrict), the casual event is intended to remind people that dating is supposed to be, you know, fun. Attendees are given green wristbands to denote they’re single or red for a wingperson who isn’t dating. The night unfolds like an unfussy party at Whitlow’s in Shaw, except you know exactly who’s down to meet someone from a crowd of up to 500.

Price: $11.


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3 Luxurious Romantic Date Ideas Around the DC Area

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You’ve Got Mail

Long before Tinder, Hinge, and Grindr, Washingtonian’s “In Search Of” ads were the way for area singles to meet.

Kathleen and Ward Rakestraw Kay on their wedding day. Photograph courtesy of Kathleen Rakestraw.

It was 1984, and after they’d emptied a few bottles of Moët together, a friend of Paula Fournier’s convinced the 23-year-old to submit a personal ad to Washingtonian.“The next morning, I was so embarrassed because I only had a vague idea of what I said,” she recalls.

A few weeks later, a package of about 50 responses arrived on her doorstep. She sorted the letters into three piles: “never,” “in a pinch,” and “tonight.” In the last group was one from Bill Fournier, a 27-year-old engineer living in Woodbridge. Their first date was at a Chinese restaurant in Tysons, where they connected over Bill’s profession—she came from a family of engineers—and a year to the day later, they married. “We would have never met any other way,” Paula says. “We didn’t run in the same circles.”

Washingtonian launched “In Search Of” in 1975. At its height in the ’80s and ’90s, it spanned more than 15 pages of the magazine each month, according to Ann Marie Grills, who at one point oversaw the section. (She’s now Washingtonian’s advertising traffic manager.) Grills and coworker Carol Simmons sifted through hundreds of responses every week, then sent the replies to the people who had placed the ads. The office accumulated an entire wall’s worth of engagement announcements, wedding photos, and baby pictures, all stemming from the ISOs.

Dating apps have largely replaced print classified ads—this magazine’s section shuttered in 2008 after entries dried up—but some elements remain constant. For one, quippy descriptions, such as those prompting you to swipe left or right on Bumble, have always been important. Kathleen and Ward Rakestraw Kay can attribute their own marriage in part to the wordplay in Ward’s ISO ad, which read, “WASP—without wife, 31, witty, wise, warm-hearted wayfaring wolverine with whiskers wishes wonderful, winsome, wacky, whimsical woman with weekend wanderlust.” Kathleen, who worked as an editor, found the diction enchanting and set up a date at Alexandria’s Union Street Public House. The couple is celebrating their 30th anniversary this year.

Paula Fournier also mentions the slight stigma around personal ads, not unlike the bad rap that dating apps and websites sometimes get today: “When people would first ask us how we met, it was awkward because that kind of thing was not looked positively on. So we would just say, ‘Oh, yeah, we met at a bar.’ Now it’s much more acceptable.”

The most notable constant, though, has to be the complaints about dating. Ward says his ad started as part of a standup routine about how hard it is to date here. “I wrote three joke personal ads, the last being the one I went with, where every word started with a ‘W’ except for the last one, which was romance. During the standup routine, I ended it with ‘womance.’ Once I was done with it, I went, ‘This is actually a pretty good ad. I’m going to use it.’ ”

 

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Marissa George

Love Is Blind

She got engaged sight unseen in the pods during the show’s DC season. While the engagement didn’t end in a wedding, the 32-year-old living in downtown DC later found love offscreen.

What’s your favorite DC date?

I love going to Bar Chinois–the scene is very intimate and low-light. My other date I love to do when I’m looking for something more fun–and I would like to go on a date with someone intelligent–I take them to Planet Word. It has this escape-room-but-not-an-escape-room called Lexicon Lane, and I really enjoy doing that trivia. On Wednesdays, they have wine, food, and you can play Scrabble for date night.

What tips do you have for singles who are not using dating apps?

I moved around a lot with the military, so every time I moved, I had to start over. I tend to just try to find an activity I like and then get involved in the community. That could be simple, like volunteering to clean up trash. It’s a great way to meet someone because you both have that shared interest.

What did you learn about love and dating during your time on Love Is Blind?

Just because someone says they want you in their life forever, that doesn’t mean it’s always going to be forever. But there is beauty in experiencing that love. As much as I would have loved to say I can go back and not have met [Love Is Blind fiancé] Ramses and gone through what I went through, there’s beauty in what we shared. It was worth the heart­ache.

Y

ou’re trying to find love in DC. How hard can it be, right?

Pretty tough, actually.

Dating apps, once applauded for their choice and convenience, have become a swamp of their own, turning romance into a digital hellscape of prompts, swiping, and meandering conversations that often don’t lead to actual dates. According to a 2023 Pew report, 46 percent of respondents said they had a somewhat negative experience with online dating platforms—and remember, dating is supposed to be enjoyable. Another 2023 survey, by Axios and the Generation Lab, found that 79 percent of college students surveyed were barely going on the apps at all.

Dating pros who work with singles in both online and offline spaces are seeing the fatigue. “People are so exhausted from online dating—they’re exhausted or disillusioned,” says Michelle Jacoby, the matchmaker and dating coach behind DC Matchmaking. “Dating has become a little crazy with all of this access to people, but people not really connecting.” Paywalls that require users to cough up cash to see their “best” matches, the blurring carousel of faces, the invention of new terms to label flaky behavior, such as breadcrumbing and orbiting—it can feel like we’ve collectively swiped left on the art of courtship itself.

In response, there’s a yearning to return to a time when you could meet a potential partner standing in line for coffee or having a flirty encounter at a party. Shifting your love life from the online to the offline world isn’t impossible in 2025. We’ve compiled a guide to dating without the apps, including where to meet people (whether in the wild or at designated dating events) and how to overcome some of the challenges Washingtonians face in the dating ecosystem. Plus, you’ll find inspiration in stories of successful meet-cutes—or solace that it really can be worse, in our cringe-worthy dating disasters.

 

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So, Where Do I Start?

If you’re looking to meet someone off your phone, consider these three recommendations. The number-one tip: Don’t stress about the outcome.

Photograph by Getty Images.

Where Like-Minded People Gather

The easiest way to meet someone you may click with? Use hobbies as a starting point, says dating coach Michelle Jacoby of DC Matchmaking. Dating apps provide limited space to express your interests, which can make it hard to gauge whether you have much in common beyond photos or prompts about “simple pleasures.” But if you hit the bouldering gym or a painting class because it’s something you actually like, you’ll know you’re already surrounded by kindred spirits—and have a good time, regardless of who you meet.

“I have been encouraging my clients to go to Meetup groups,” says Jacoby. “Be in the moment and just have fun.”

Active types can join recreational groups, from DC Bike Party to hiking clubs that explore Shenandoah National Park. Book clubs at shops such as Lost City Bookstore in Adams Morgan and Solid State Books on H Street are great places to find fellow bibliophiles, and discussions on the latest read can turn into deeper conversations. A bonus: You’ll likely encounter the same faces repeatedly.

Places That Lend Themselves to a Natural Approach

Not every spot is going to be ideal for sparking conversation. (Think silent libraries or thumping nightclubs.) Seek out places with openings for easy introductions and the right environment to continue chatting. For example, Washington has a vibrant social-dancing scene, including Thursday salsa socials at La Cosecha at Union Market, blues dancing at Maryland’s Glen Echo Park, and weekly swing sessions at Josephine Butler Parks Center near DC’s Meridian Hill Park. You don’t need to bring a dance partner, which means you’ll meet people as you pair off throughout the evening.

Or, if you’ve got a dog, consider it your wingman: Start frequenting a local dog park or canine-friendly bars such as Dog Daze Social Club in Logan Circle, where pups are a natural opener for owners, who already have something in common. And while recreational sports leagues may feel like a DC cliché, Jacoby puts them at the top of her list of locales for meeting potential partners. They’re intended to be social, with designated opportunities to mingle before or after games in groups such as Stonewall Kickball League or at a Dill Dinkers’ Open Play pickleball clinic. Even a bar with billiards—Nice & Easy in NoMa or Carpool in Arlington—can provide a chance to engage with new people.

Anywhere, Really

Opportunities to meet someone special can be found virtually everywhere, but many people remain absorbed in their own world, wearing earbuds and rushing from place to place. “The pandemic made us even more introverted, and people are really longing for that personal connection, which is ironic because they’re looking down at their phones,” says Jacoby. “Talk to people and look up, and don’t bring your phone—turn it off.” A simple compliment or amiable remark can spark a conversation. Jacoby’s advice: “Treat every stranger like a friend.”

Of course, there are concerns about appearing creepy or overstepping, especially for men. Context matters, cautions men’s dating coach Erika Davian. Approaching someone in a vulnerable setting—a gym, a doctor’s office, during yoga—can come off as intrusive rather than charming. The key is genuine curiosity, not an agenda, she says. If you’re trying to “get something” (say, a number or a date), the interaction can feel transactional.

In a work-driven city such as ours, Jacoby recommends leaving that networking mindset at the office. Approach interactions with openness, not interrogation. “People are too focused on qualifying the buyer,” she says. “Stay open and just enjoy meeting new people.” Everyday moments such as waiting for coffee or commuting on the Metro can lead to unexpected connections—if you’re open to it. (Don’t believe us? Scroll down for stories of real-life meet-cutes.)

 

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Joan Vassos

The Golden Bachelorette

The 62-year-old Rockville resident found love while dating a group of senior singles as TV’s first-ever Golden Bachelorette. Here, she answers some of our dating questions.

Do you have a local first-datespot you recommend?

I did usually go in Bethesda because it’s central to a lot of people if they’re from DC or Virginia. I’d go to Woodmont Grill, I’d go to Black’s [Bar & Kitchen], I love Mon Ami Gabi. They all have nice bars, great atmosphere. Those three places were always good.

How is dating on The Golden Bachelorette different from dating at home?

Dating, not just in Maryland but in general, at this age is hard. I did a dating website. I didn’t love that–it felt like a job. You had to spend a lot of time texting strangers and trying to figure out if their profile was truthful, which I found out a lot of times wasn’t. Dating on national TV–though that in itself is weird–the guys are vetted for you.

What advice do you have for DC-area singles?

I had a tendency to go for the bad boys or people that are just epic­ally fun, but when you’re thinking about what you want your life to look like, find the person who fits those categories. Concentrate and aim for what you want your long-term person to be.

 

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Meet-Cutes

Sometimes, that fairytale meeting really does happen. Here are five sweet stories of real-life romantic encounters.

Next Stop: Love

“We were both living in Virginia at the time, and we’d take the Yellow Line into DC every day. We rode in the same car and got off at the same stop, but we’d exit in different directions. During my commute, I would text my friends about my ‘Metro crush.’ I would listen to ‘Crush’ by David Archuleta. And this was in 2022, so everybody was wearing masks—at this point, I hadn’t even seen his whole face. I remember texting my friends the day the mandate was lifted, to let them know he was still hot without the mask! I never thought anything was going to happen. We never talked until one day about four months into riding together. We got off at our usual stop and went our separate ways, but suddenly I felt a tap on my shoulder. It was him. He said, ‘Hey, I’m moving into the city, so this is my last day on this Metro line,’ and he asked for my number. The whole time I was texting my friends about him, he was going into work and telling his coworkers about me. They actually helped him game out how to approach me. When he proposed, he had the ring box embossed with a map of the Metro. To this day, he’s in my phone as ‘Metro Crush.’ ”

—Brooke, 31, librarian

 


 Cupid’s Claw

“Both of us worked at José Andrés restaurants: I was a prep cook at Minibar, and my now-husband, Simon, was a sous chef at China Chilcano next door. At Minibar, we got shipments of whole lobster, but we only cooked the tails. It was my job to drop the claws off at China Chilcano every day, which was how I got to know the staff over there. I honestly never noticed Simon at first, but he noticed me right away—he tells me now, a decade later, ‘You had the butt.’ ”

—Rochelle, 34, pastry chef

 


Silver Lining

“I’m originally from Tennessee, and I had moved to DC for a job. I made some friends in my apartment building, and I got invited to go to a Nats game. I’m not a big baseball person—when I saw Nats hats, I thought it was a Walgreens logo. So I went, and we’re not even halfway through and it started pouring down rain. Somebody suggested going to Salt Line across the street and grabbing a drink, until we figured out how long the rain delay would last. They have an outdoor bar with an [overhang], so you can run underneath. There was a little space open, and I said, ‘Are ya’ll in line?’ And my now-husband said, ‘You’re not from here—you said ya’ll.’ We started talking, and he asked for my number. I normally wouldn’t do that, but I was like, ‘Sure, why not?’ People said, ‘Oh, you’re not going to meet a husband in DC.’ I pushed it out of my mind, and it ended up working out really well for me. It just seemed like fate.”

—Meg, 34, attorney

 


Rats Amore

“I met up with some guys at my friend’s place in Logan Circle for a boys’ night. We had just started on the walk from his rowhouse to Dupont when we ran into his neighbors outside in their backyard. Turns out they were throwing a birthday party for one of their roommates. My friend got to chatting with them about their mutual rat infestations—they lived in the same row of houses, after all—and they invited us inside to check out the holes the rats were using to sneak into their place. I had been expecting to go out to the bars rather than crashing a stranger’s birthday party, so I was feeling a little out of place, but I grabbed a beer and hung out in the kitchen. That’s when Alex, the birthday girl, came over and introduced herself. I had noticed a bunch of cow decor all over the house, so I asked her about it—she really loves cows, which was a great entry for me because my family owns a farm. After the party wrapped up, she invited me to Shenanigan’s with her and her friends. We danced, got Jumbo Slice, she asked for my number, and I walked the whole way home from Adams Morgan to the Waterfront.”

—David, 26, government worker

 


Art and Heart

“I was going to the National Gallery of Art, just as a single date with myself. I was walking around the Impressionist gallery, and I saw this woman standing in front of this big painting by Mary Cassatt. She was tall and had bright-blue eyes, very beautiful. The painting she happened to be standing in front of was a painting I actually wrote a report on—I was attending American University. She appeared to be alone, so that gave me the confidence to go up to her. I asked, ‘Do you like the painting?’ She said, ‘Yeah, it’s so beautiful.’ Then I went, ‘It’s my favorite in the gallery. I wrote a report on it for school.’ She took me over to this giant painting of Napoleon because she’s a European-history nerd. She was explaining that she had written a report on Napoleon for school. I asked, ‘Do you want to walk around the other galleries together?’ We went from room to room and talked about history and art and our degrees. We probably hung out for a couple of hours. Today is actually our two-year anniversary.”

—Claire, 22, conservationist

 


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Bartenders Spill

Yes, they can spot a first date from a mile away. Here, mixologists share how they sense if it’s love at first sight or a dating disaster before you can say, “Check, please!”

First Dates

“You can tell everyone’s on their best behavior. Spine straight, using napkins, delicately drinking,” says Beth Lindsay, who has witnessed hundreds of first encounters as the owner of Board Room, a 12-year-old board-game bar in Dupont Circle. “And then when the date gets up and goes to the bathroom, they gulp their drink down and look at their phone to text.”

Meanwhile, David Strauss, owner of the Mount Pleasant speakeasy OKPB who has spent nearly three decades in the restaurant industry, has observed that first-daters will often order fewer drinks (to avoid inebriation) but stay longer. “Which is by no means a complaint,” he hastens to add. “We love watching from the outside and seeing how things play out. Ninety-nine percent of the time when you walk in, the bar staff is rooting for you to work out.”

Doomed Relationships

As anyone who’s played a heated round of Monopoly or Catan knows, board games can reveal some unsavory aspects of participants’ personalities. The Board Room’s Beth Lindsay describes a couple who came in to play Battleship. “He was really into it,” she says. “The young lady left to use the restroom, and he took a picture of her board. Later on, he used the restroom and I [told her], ‘Just letting you know, that guy’s cheating.’ ” Because some games take only a few minutes to complete, Lindsay sees a lot of serial daters: “My personal record is a gentleman I saw come in three times on a Saturday with different dates.”

Sometimes, it’s not what people do but what they say. Shelly Caviness, manager of Morris American Bar in Mount Vernon Square, recalls a red-flag moment: “I overheard a girl say, ‘I talked to my mom about you,’ and the guy said, ‘Yeah, I think it’s too soon for any of that.’ They split the bill afterwards.” If a meetup isn’t going well, she says she’ll get that look, and she has no problem asking someone to leave if they make their date uneasy. “We’re always checking to make sure you are safe and having a good time. If you’re feeling uncomfortable, please tell one of us.”

True Love

Believe it or not, servers want your Hinge date to turn out to be a soul connection almost as fervently as you do. “As much as we love cocktails, we really do love hospitality and relationships,” says Strauss. Bartender Zoe Pipines recalls a man who was so nervous about his date that he came into the Dupont Circle Mediterranean restaurant Balos Estiatorio a day early to check out the menu. The next day, his blind date ended quicker than expected. He stayed to order food and struck up a conversation with a woman sitting near him. They chatted until close and are still dating months later. Pipines knows because they’ve come in for their “anniversary” each month.

Says Strauss: “We talk a lot about it as a group. Like, ‘Remember that couple that came in on Friday? They stayed for three more and left together.’ We love seeing that. We get a front-row seat to the best cross section of humanity every night.”


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First Impressions

So you’ve met someone and it’s time to schedule a first date. Finding the perfect spot can be a balancing act, especially as you’re just getting to know each other. Here are nine destinations to consider, depending on your first-date vibe.

Photograph courtesy of Barca.

If you want a bar with reservations, to avoid awkward waits:

Barca in Old Town for wine by the waterfront; The Pub & the People in Bloomingdale for drinks and snacks in a cozy tavern; or Service Bar on U Street for cocktails and mocktails in a casual space.

Photograph by Hawkeye Johnson Photography.

If you want a nice daytime cafe with ample seating:

Yellow in Union Market for creative coffee drinks and pastries; Gustave in Del Ray for French baked goods in a sunny beer garden; or Ellē in Mount Pleasant for lattes at a table for two.

Photograph by Getty Images.

If you want an active date where you can easily chat:

Perch Putt in Tysons for mini-golf with a tiki bar; the United States Botanic Garden for a floral stroll and (if it’s going well) an easy transition to more museums; or Pinstripes in North Bethesda for bowling in sleek lanes with a full menu.

 

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Dating Disasters

Not every date is going to be a dream, but some are worse than others. Here are six stories of meetups gone wrong.


Pop Quiz

“I was still learning my buses and trains, so I texted to say, ‘Hey, I’m running late.’ Minutes later, I get this text that says, ‘If you can believe it, this girl does not care about me, she’s literally going to be 25 minutes late, this bitch.’ I was like, ‘I think you texted the wrong person.’ When I arrived at Church Hall, he had one of those huge tankards of beer, something that looks out of medieval times. And he’s already been drinking it. He goes, ‘I actually started looking you up while I was sitting here. I just want you to know that you answered this question on Quora about how you lost your virginity, so you should probably scrub it from the internet.’ I went back later and scrubbed it, of course, and to find that, you had to go through five pages of Google. He said, ‘Because you’re so late, I’m not going to buy you a drink unless you can answer these different questions.’ Then he quizzed me on something to do with European history, but he was really upset that I actually got the questions right. The bartender slipped me a note on a napkin when the guy went to the bathroom: Hey, do you need help? I looked up at him and said, ‘Honestly, this is hilarious. I just want to see how it can get worse.’ ”

—Franny, 27, project manager

 


Hide and Seek

“I met this guy for a date at the Georgetown waterfront. We were walking along the path that runs along the park when suddenly, without saying anything, he started running. I was really concerned—I thought he must have seen a bee or was having a panic attack. Then he went and hid behind a tree. I went over and asked if he was okay, to which he replied, ‘Oh, my God—I just saw my parents and they weren’t supposed to be here.’ I totally under­stand that’s an awkward situation, but he was almost 30. The rest of the date lasted no longer than ten minutes.”

—Maddie, 29, consultant

 


Deal Breaker

“She seemed fun, a little on the wild side—a break from the attorney lifestyle. This was during the pandemic. [Her friend] had been doing some comedy clubs and booked a gig somewhere in a farmland area where they could have an outdoor event. The day before, she brings up, ‘So listen, I do owe some money to a coke dealer in DC. I promised to push a little product at the show to help pay them off. So don’t freak out if I’m going from table to table. That’s fine, right?’ There was a part of me that said, Well, this should not be a surprise to me at all, based on everything I know about this woman. She literally just disappeared for a few minutes, I tried not to look where she was going, and then she came back and said, ‘Oh, sorry, just had to take care of something’—very subtle. At the end of the night, I was like, That was a bridge too far for me.”

—David, 41, attorney

 


Cast Away

“The reason I wanted to go on a date with him was because he had a motorcycle. As soon as I saw him, I noticed he was wearing one of those removable casts. He told me he’d been in a motorcycle accident, so the motorcycle was destroyed and now I could never ride it. He proceeded to take off the cast and put it on the table in front of me! It absolutely reeked of BO—I was disgusted. The whole time, the stink from this cast is wafting up at me.”

—Ruth, 26, public-relations rep

 


Train to Nowhere

“I was on a first date with this guy I felt I had a real connection with, and I’d mentioned I was doing some modeling work. He told me he’d actually just been part of a local PSA about pedestrian safety, which I thought was cool. The next day, I was on the Metro and I saw this PSA with a photo of him crossing a crosswalk! I texted him a picture of it. After several days, he hadn’t responded, so I was like, ‘Okay, now I just have to stare at this guy on my commute.’ The PSA was up for several months—on the Metro, on the sides of buses, on the Old Town Trolley, which I took to work every day. He ghosted me, but he was everywhere.”

—Kelly-Lynne, 36, content creator

 


Wife Guy

“People were still cautious about meeting up because of the pandemic, so a Hinge match and I decided to do our first date over FaceTime. Our text exchanges over that week had been very flirty, so I wore a lacy tank top that was basically lingerie. On the third ring, a woman answered his phone. I was shocked because he’d told me he was widowed and also because I was a quarter naked. She told me she was his wife and, in spite of what he’d told me, she was very much alive. Not only did she show me her ring—beautiful rock, by the way—but she happened to walk down her hallway, which I saw was lined with their wedding photos. She was super-nice and even told me she wasn’t angry with me. You could kind of just tell in her face that she just felt sorry for me.”

—Amber, 37, consultant

 


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Match Game

Singles everywhere like to say their city is a hard place to date in, but each location has its own challenges. Here, area matchmakers and dating coaches share some of the problems specific to Washington and how you can maneuver around them. Hint: It comes down to changing your mindset.

Challenge #1

Location Frustration

There’s some truth to the jokes about District residents not wanting to cross the river to Arlington and vice versa. But you may have to look even farther—we’re talking beyond the Beltway—for The One. Michelle Jacoby of DC Matchmaking encourages clients in the city to be open to the idea that their future partner could live in, say, Annapolis or Baltimore. One barrier? “Something that’s perhaps unique to DC is that a lot of people don’t have cars, especially women in their thirties,” says Jacoby. She’ll set up clients near Metro stops if they request it (and they do), but a Zipcar membership could be an investment in your love life that expands the pool of potential connections.

 

Challenge #2

Drawing Party Lines

DC is mostly blue, so perhaps it isn’t surprising party membership is a major concern for singles here. In particular, being MAGA is a red flag for many. “The number-one deal breaker we get is ‘a Donald Trump supporter,’ by far,” says Callie Harris, a senior matchmaker at Three Day Rule. Though it seems impossible to disentangle political ideologies from personal values, Ali Deckelbaum and Molly Dresner, cofounders of the Court, a local matchmaking service, encourage people to look beyond Democrat and Republican. “We try to get deep into your stance on specific issues, instead of just broad-stroke labels,” says Dresner. Matchmaker Natalie Fry of It’s Just Lunch Washington DC recommends avoiding politics on a first date: “Focusing on shared values and interests—that can transcend differences there. Someone who is living a life of purpose and meaning is really underlying that preference for the same political affiliation.”

 

Challenge #3

Dating a Résumé

All of the matchmakers we spoke with say app culture has impacted dating. Singles have become accustomed to filtering potential romances by somewhat meaningless metrics that encourage them to make swift judgments based on minimal information. “You’re forced to filter by things that don’t indicate compatibility,” says Harris. “We tend to think, ‘Oh, they’re asking me to filter by height, so that must mean it’s important.’ ” But in DC, experts say these snap judgments go well beyond the basics. “We have a ton of clients who are super-competitive and are into job titles and higher education, number of languages spoken, how many countries they have visited,” says Dresner. First, take a breath. Then consider what’s really important in a partnership: Is it a high-level security clearance and a passport filled with stamps? Or traits such as trustworthiness and empathy?

 

Challenge #4

Too Busy to Get Busy

According to the matchmakers, stereotypes about workaholic Washington manifest in dating. It’s hard for potential couples to gain momentum when dates are few and far between due to scheduling conflicts. Fry suggests adapting the same mindset you would in business: “Schedule dedicated time for dating, just like you would important work meetings.” Jacoby shares the story of a client she kept introducing to compatible matches, but his busy travel schedule for work kept any romance from blooming. However, when the pandemic hit, he was forced to stay put in Adams Morgan, and Jacoby connected him with a woman in Loudoun County: “He ended up getting married because he couldn’t go anywhere.”

 

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Derek Sherman

Married at First Sight

On the DC season of Married at First Sight, the 32-year-old met and married his now ex-wife at the altar. Currently living in Arlington, he shared his thoughts on love and dating.

What’s your dream date?

I’m a sucker for different activities. It would be going into DC, starting off at Whiskey Charlie, then going to Artechouse. Maybe checking out one of the museums on the way, then going to Swingers. My favorite dates have been at Christmastime, going to Enchant or towards Manassas to check out the Christmas-light shows.

What’s the number-one lesson you learned during Married at First Sight?

Honestly, one, patience, and two, being yourself. One of the hardest things from doing my show is trying to balance acting like you’re married and being yourself, and at the same time trying to impress them like a first date. The thing that helped me the most was just being true to myself, and again, patience and listening.

Do you have any advice for area singles?

Just getting out there! For singles in the DC area, one of the best things they have going for them is the diversity of what’s around you. We get pushed into our own bubbles, but just expanding those is the best advice. There’s so many different events happening. It’s a great way of having an icebreaker if it’s a new experience.

 

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Meet and Greet

One convenient aspect of dating apps? You know everyone is looking to meet someone. Dating events apply that same principle, just to the offline world. These days, you’re not limited to speed dating: Here’s the rundown on three events around DC.

Photograph of couple courtesy of The Feels DC.

Singles on Socials

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The vibe: Happy hour.

Age group: Some events are designated for the twenties crowd, while others cater to thirty- and fortysomethings.

Icebreaker: Question cards to spark conversation—think “What’s your favorite Italian restaurant?”

After spending all day on a computer screen at work, who wants to transition to a phone screen for dating? That’s the idea that inspired Sarah Goldenberg to create an after-hours alternative to apps. Women come to the space first, spending a half hour getting comfortable and acquainted with one another before men enter the venue. From there, it’s typically a low-pressure happy hour at a bar, though there have been one-off evenings at the Phillips Collection’s after-hours program or even a run club for a change of scenery. Attendance ranges from 60 to 250 people.

Price: $20 to $40.

 

The Feels

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The vibe: Intimate and a little woo-woo.

Age group: A wide swath from twenties to fifties.

Icebreaker: Facilitators share an embarrassing dating story.

Founder Allie Hoffman takes inspiration from psychologist Carl Jung and writer Joseph Campbell’s “hero’s journey” as well as her own experience with meditation and circlework. The event starts with drinks and mingling before settling in for an introduction and learning what type of body contact attendees may experience during the program. Then they’re split into rotating pairs to move through prompts that get under the surface. For example: What’s something you learned from your parents and something you’ve had to unlearn? Duos later reflect on each other’s responses, followed by a “somatic” element—a hug, extended eye contact—to be fully present in seeing how someone makes them feel.

Price: $83.

 

Cuffing Season

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The vibe: A night on the town.

Age group: Between 23 and 33.

Icebreaker: Bingo boards with squares such as “Find someone with a tattoo” for an excuse to approach someone.

Run by bar influencer Bruce Allen (@drinksinthedistrict), the casual event is intended to remind people that dating is supposed to be, you know, fun. Attendees are given green wristbands to denote they’re single or red for a wingperson who isn’t dating. The night unfolds like an unfussy party at Whitlow’s in Shaw, except you know exactly who’s down to meet someone from a crowd of up to 500.

Price: $11.


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You’ve Got Mail

Long before Tinder, Hinge, and Grindr, Washingtonian’s “In Search Of” ads were the way for area singles to meet.

Kathleen and Ward Rakestraw Kay on their wedding day. Photograph courtesy of Kathleen Rakestraw.

It was 1984, and after they’d emptied a few bottles of Moët together, a friend of Paula Fournier’s convinced the 23-year-old to submit a personal ad to Washingtonian.“The next morning, I was so embarrassed because I only had a vague idea of what I said,” she recalls.

A few weeks later, a package of about 50 responses arrived on her doorstep. She sorted the letters into three piles: “never,” “in a pinch,” and “tonight.” In the last group was one from Bill Fournier, a 27-year-old engineer living in Woodbridge. Their first date was at a Chinese restaurant in Tysons, where they connected over Bill’s profession—she came from a family of engineers—and a year to the day later, they married. “We would have never met any other way,” Paula says. “We didn’t run in the same circles.”

Washingtonian launched “In Search Of” in 1975. At its height in the ’80s and ’90s, it spanned more than 15 pages of the magazine each month, according to Ann Marie Grills, who at one point oversaw the section. (She’s now Washingtonian’s advertising traffic manager.) Grills and coworker Carol Simmons sifted through hundreds of responses every week, then sent the replies to the people who had placed the ads. The office accumulated an entire wall’s worth of engagement announcements, wedding photos, and baby pictures, all stemming from the ISOs.

Dating apps have largely replaced print classified ads—this magazine’s section shuttered in 2008 after entries dried up—but some elements remain constant. For one, quippy descriptions, such as those prompting you to swipe left or right on Bumble, have always been important. Kathleen and Ward Rakestraw Kay can attribute their own marriage in part to the wordplay in Ward’s ISO ad, which read, “WASP—without wife, 31, witty, wise, warm-hearted wayfaring wolverine with whiskers wishes wonderful, winsome, wacky, whimsical woman with weekend wanderlust.” Kathleen, who worked as an editor, found the diction enchanting and set up a date at Alexandria’s Union Street Public House. The couple is celebrating their 30th anniversary this year.

Paula Fournier also mentions the slight stigma around personal ads, not unlike the bad rap that dating apps and websites sometimes get today: “When people would first ask us how we met, it was awkward because that kind of thing was not looked positively on. So we would just say, ‘Oh, yeah, we met at a bar.’ Now it’s much more acceptable.”

The most notable constant, though, has to be the complaints about dating. Ward says his ad started as part of a standup routine about how hard it is to date here. “I wrote three joke personal ads, the last being the one I went with, where every word started with a ‘W’ except for the last one, which was romance. During the standup routine, I ended it with ‘womance.’ Once I was done with it, I went, ‘This is actually a pretty good ad. I’m going to use it.’ ”

 

Reality Check

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Marissa George

Love Is Blind

She got engaged sight unseen in the pods during the show’s DC season. While the engagement didn’t end in a wedding, the 32-year-old living in downtown DC later found love offscreen.

What’s your favorite DC date?

I love going to Bar Chinois–the scene is very intimate and low-light. My other date I love to do when I’m looking for something more fun–and I would like to go on a date with someone intelligent–I take them to Planet Word. It has this escape-room-but-not-an-escape-room called Lexicon Lane, and I really enjoy doing that trivia. On Wednesdays, they have wine, food, and you can play Scrabble for date night.

What tips do you have for singles who are not using dating apps?

I moved around a lot with the military, so every time I moved, I had to start over. I tend to just try to find an activity I like and then get involved in the community. That could be simple, like volunteering to clean up trash. It’s a great way to meet someone because you both have that shared interest.

What did you learn about love and dating during your time on Love Is Blind?

Just because someone says they want you in their life forever, that doesn’t mean it’s always going to be forever. But there is beauty in experiencing that love. As much as I would have loved to say I can go back and not have met [Love Is Blind fiancé] Ramses and gone through what I went through, there’s beauty in what we shared. It was worth the heart­ache.

Illustrations by Connie Zheng
Photograph of Joan Vassos by Ramona Rosales.
Photograph of Derek Sherman courtesy of Sherman.
Photograph of Marissa George by Adam Rose/Netflix.
This article appears in the March 2025 issue of Washingtonian.

More: FeaturesDC dating
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Damare Baker
Damare Baker
Research Editor

Before becoming Research Editor, Damare Baker was an Editorial Fellow and Assistant Editor for Washingtonian. She has previously written for Voice of America and The Hill. She is a graduate of Georgetown University, where she studied international relations, Korean, and journalism.

Daniella Byck
Daniella Byck
Lifestyle Editor

Daniella Byck joined Washingtonian in 2022. She was previously with Outside Magazine and lives in Takoma.

Kate Corliss
Kate Corliss
Junior Staff Writer
Kim Habicht
Kim Habicht

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