night out ideas

Start out at Bar Mini, a fancy bar with fabulous cockails.  Definitely make a reservation!
https://www.minibarbyjoseandres.com/barmini/
Then, if no one is wearing heels, walk 15 minutes north on 9th St. to The Dabney.  They take a few walk-ins at the bar, but we would definitely recommend a reservation here too.  The vibe is very NYC, with a coziness due to the open kitchen and wood-burning hearth.  The food is some of the best in D.C. They also have a coktail bar downstairs if you want to keep the party going!
https://thedabney.com/
What to wear:  Sadly, you can pretty much wear jeans anywhere in D.C., but use this as an excuse to take it up a notch.  Take this occassion to bust out your cocktail attire.
Have fun!

The Dabney Restaurant, Washington D.C.

fancy night out

The John F. Kennedy Center for the Perfoming Arts, Washington D.C.

go high/go low

Go to the opera and then to a dive bar!
Check out the schedule of performances here:
https://www.kennedy-center.org/
Make sure you purchase tickets beforehand.  Get a glass of champagne pre-show or at intermission.  Take it outside, check out the fountains and the view.
After the show, keep the musical theme going with Mr. Smith's (a 15 min walk or 5 min cab ride):
http://mrsmiths.com/
It's a fun vibe, and there is pub food if you arrive hungry.
What to wear: Accept the fact that you will be dressed up for the dive bar, and dress up!  No need to go cocktail attire for the Kennedy Center, but you would not look out of place.  At the least, put on something nicer than a pair of jeans.
Have fun!

Camp Wharf, Washington D.C.

cuddle up

Cuddle up on the beanbags while watching an art installation at Artechouse:
https://www.dc.artechouse.com/
You will need tickets, and be sure to check out the first in the U.S. Augmented Reality bar serving drinks activated with a free AR mobile app.
From there, walk 10 minutes to the wharf.  Walk around, check out the shops, the fish market and the variety of dining options that abound:
https://www.wharfdc.com/restaurants/
Finish up the night cuddling up on a bench with some s'mores.  Bonus points if you bring a flask of Baileys:
https://www.wharfdc.com/restaurants/camp-wharf-at-the-firepit/
What to wear:  Here, you can wear jeans.  Some of the restaurants at the Wharf are upscale, but you can still get away with jeans if you look nice.
Have fun!