Date ideas in the DC area from a local matchmaker

It’s time to debunk the myth that D.C. is a difficult city for dating and finding one’s true love. That’s the mission of Michelle Jacoby, the founder, owner and CEO of DC Matchmaking, a boutique matchmaking and dating coaching company based in the D.C. area. She is also the author of the book, “Never Waste Time on the Wrong Man Again,” published in April 2021.

According to Jacoby, there’s a lot to offer in the District.

“We have the most phenomenal demographic of singles here. We have highly educated, very healthy, well-traveled, interesting, passionate, amazing people here in D.C., and it’s a phenomenal place to date,” she said.

Of course, dating isn’t easy, but “dating is just hard wherever you are,” she said. “Dating is a skill, and not everyone is skillful at it.” That’s where Jacoby comes in.

She spoke to WTOP about her recommendations on where to go for a fun time.

It’s easy to default to Netflixing at home or going to dinner at a “usual” place, but Jacoby recommended adding a little variety to date nights to spice up one’s relationship. “It makes a relationship fun,” she said.

Here are some easy and creative ideas for locals and visitors in the D.C. area for a first date or a date with a longtime significant other.

D.C. date ideas

For those dating on a budget, consider going to the Kennedy Center’s Millennium Stage for free, daily events. The stage includes film screenings, live performances, standup comedy, as well as opera and orchestral performances.

If you’re interested in musical performances that are lesser-known, use the Sofar website that Jacoby described as “the speakeasy of small, live music.” This website lists “secret concerts” in intimate venues with the addresses not revealed until a few days before events.

Those ready for an adventure can check out Watson Adventures, which allows couples and groups to be able to turn their favorite neighborhood into a scavenger hunt. Scavenger hunts can be done in several areas of the District, including the American Art Museum and National Portrait Gallery, the National Zoo and Union Station.

Jacoby recommended activities like paddle boats at the Tidal Basin, the “high-end putt-putt/mini golf experience” known as Swingers and also games and brews at Board Room in the Dupont Circle neighborhood. Other fun events can be found at Crazy Aunt Helen’s in Capitol Hill, where they host the Musical Mondays open mic along with several other events.

Jacoby also suggested NoMa’s outdoor beer garden, Wunder Garten, adding that they can offer “really neat events there that are not just about beer.”

When it came to what to nosh on, Jacoby recommended Zaytinya by José Andrés, vegan restaurant Elizabeth’s Gone Raw and also pizza restaurant Comet Ping Pong.

Maryland date ideas

Further out from D.C. proper, locals and visitors looking to date in Maryland can head to Glen Echo Park, which includes dancing classes, art exhibitions and more.

In particular, Jacoby recommends the Spanish Ballroom for swing dancing, square dancing, folk dancing and even tango and milonga dancing.

For a more relaxing date, visit the Strathmore in Bethesda for afternoon tea with local musicians filling the air with music. Be sure to check out the venue’s full calendar for more events.

Virginia date ideas

Get physical by playing pickleball. Jacoby said it’s “a great thing to do with a partner … and friends” and a great way to meet people too. There are several pickleball courts in Arlington to consider.

Afterwards, head to Old Town Alexandria for a ghost tour pub crawl for public tours and private tours year-round with a costumed guide who will traverse through dark alleyways and ghostly taverns.

Not far, The Birchmere in Alexandria can also be found for more musical entertainment.

Michelle Goldchain

Michelle Goldchain’s reporting has focused primarily on the D.C. area, previously working as Editor of Curbed DC for Vox Media and Audience Growth & Engagement Editor for Washington City Paper. She is the author of “D.C. by Metro: A History & Guide.” She also reports for 'Artsplained' on YouTube.

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