51 First Date Ideas
Visit the Hillwood Museum & grab food in Cleveland Park (I suggest Dolan Uyghur). Often they have after hour music performances
Go to the Postal Museum and afterwards explore Union Market
Visit the Zoo, but stop by the Target, Streets Market or CVS at Cleveland Park and stock up on snacks
Explore the sky at the Phoebe Waterman Haas Public Observatory and then take a walk through the US Botanical Gardens on the way to We the Pizza for food or Hawk 'n Dove for a drink
Rent a kayak or a paddleboat from Georgetown and then grab a drink at The Berliner or at Foxtrot
Play tourist and rent a swan boat at the Tidal Basin, take a tour of the US Mint, and then find your way to the Waterfront for drinks at Tiki TnT
Visit a house of worship such as Sixth & I for a show such as a book talk or a podcast recording, or the National Cathedral for a play or performance
Walk through your local neighborhood and enjoy the seasonal decorations, grab coffee beforehand
Check out your local bookstore for author talks, and grab a drink beforehand nearby (Politics and Prose, Mahogany, Loyalty, Lost City, Solidstate Books, etc)
Enjoy the Heurich House beer garden (but they also host a very cute holiday market)!
Do mini-golf, if the weather is nice go to the East Potomac Wharf, or if you prefer an indoor boozy option, try Swingers (tip: get the drink package)
Play board games at The Board Room or at Labyrinth Games
Catch a comedy show-- Capitol Cider House, Eaton, Town Tavern, Bier Baron, Cafe Saint-Ex, Wonderland Ballroom, or Busboys and Poets
Enjoy crafternoons at ShopMadeInDC in Georgetown and wander to the Mall to catch the sunset
Grab your roller skates and go to the Anacostia Skate Park. (Skates are usually free to rent, but might not be available right now)
Or, if it's the season grab your ice skates and head to Georgetown or the National Gallery of Art
Support your local cinema such as Miracle Theater, Landmark E St, or Suns Cinema
Get a day pass and go climb at Brooklyn Boulders, or take the trip out to Pentagon City and Earth Treks
Visit a local embassy for a film showing, some favorite venues include the Embassy of France, Austria, Finland, Czech Republic; and the Former Residence of the Ambassador of Spain
Check your favorite beer gardens such as Wunder Garten, Dacha, Atlas Brewery, or MetroBar for programming
Head to Mess Hall for a pig or tuna butchering--they have them on occasion!
Explore one of the plethora of farmers' markets
Decorate doughnuts with District Donut (they sometimes have workshops or beer pairings!) or try a seasonal ice cream fleet from Ice Cream Jubilee
It's hard for two people to play in a trivia team, but Union Market, Hotel Zena, Red Bear Brewing, and Wunder Garten often have bingo
Enjoy the Kennedy Center's Reach outdoor performances. Or, inside (MyTix has discounted tickets for young professionals)
Watch a drag show --often you can find them at Red Bear, Mercy Me, Dupont Underground.
Visit Georgetown not to shop, but rather to attend a free event at Patagonia (often films or lectures) or Outdoor Voices (a workout class)
Learn something new at a Profs & Pints lecture
Explore one of D.C's speakeasies such as The Mirror, the Gibson, Left Door, SIlver Lynan, etc.
Volunteer! There's many one-time opportunities with the Capital Area Food Bank, District Clean-Ups, Kingman + Heritage Islands, and Kenilworth Aquatic Gardens, or Common Good City Farm
Visit the new Planet Word Museum and enjoy the newly renovated Franklin Park afterwards
Check out one of the wine bars in the city such as Barcelona, Primrose, City Winery, Eastern Wine Bar, or Vin Sur Vingt
Get to know DC Sports! There are hockey tickets that start ~$63, baseball ~$13, soccer ~$15, and basketball ~$10
Visit President Lincoln’s Cottage, and after visit a local brewery such as Hellbender, City State, and Right Proper, Other Half, or Atlas Brew Works
Take a hike through Rock Creek Park, Glover Archbold, Dumbarton Oaks, Anacostia River Trail, or Theodore Roosevelt Island
Wander the Philipps Collection which was the first modern art museum in America or take a trip off the beaten path and go to the Kreeger Museum
Explore one of the Food Halls in D.C. such as The Block, The Roost, Union Market, or Eastern Market--and soon Love, Makoto
Eat some oysters at Pearl Dive, Old Ebbitt Grill, or Hank's Oyster Bar
Enjoy one of the DC Neighborhood Heritage Trails, I particularly like the Lift Every Voice (Georgia Ave/Pleasant Plains), River Farms to Urban Towers (Southwest Heritage Trail), and City Within a City (Greater U Street Heritage Trail).
Visit smaller galleries around the city such as Anacostia Arts Center or Homme
Rent a karaoke room at Wok and Roll and much down on New Big Wong afterwards
Window shop plants that you may or may not kill--(I find window shopping for furniture is a great way to learn about someone generally)
The Bonsai Museum and the Arboretum or even Kenilworth Gardens is a feast for the eyes, especially during seasonal changes. Grab a drink aferwards at Supreme Core
Play some games such as pinball or billiards at Players Club, Tilt, Bread Soda, or Rocket Bar
Take a boutique boxing workout class together such as Rumble, Urban Boxing, or NuBoxx
Wander around H. St and explore some favorite spots such as Pie Shop, Little Miss Whiskeys, Thamee, Maketto, Granville Moore, and CopyCat
Get out to Gravelly Point, National Harbor, Baltimore, Old Town Alexandria, Mount Vernon (which often has festivals!), Clarendon, or Ballston Quarter if you want a quick escape from the city.
Catch a late night jazz show (one of my favorite spots is Jojo's) or maybe an a cappella performance
Watch a play at a local theater, besides Warner Theatre and Woolly Mammoth Theatre Co, there are many local community theaters too
Find some of the less popular sites such as Einstein, the Titanic Memorial, Carter G. Woodson, the Barbie Pond, the Chair, or the zero marker
Go to the base of the Washington Monument at night and see the Capitol, the Lincoln Memorial, the World War II Memorial, and the White House all from one spot. It's quite romantic.