Parents Night Out Processional
If you and your partner had 2-3 hours on a Saturday night to get a drink, a few appetizers, and a dessert, where would you go? Ideally it'd be (1) three separate places within walking distance of one another, (2) in DC, Arlington, or Alexandria, and (3) generally quiet enough to have a conversation without yelling.
We like: (1) a good cocktail and/or beer (Rogue, Victory, or Founder's for example), (2) just about any type of cuisine with a range of textures, spices (heat is ok!), and veggies/meats, and (3) flavorful but not necessarily super sweet desserts.
I recognize this could be a challenge; I over- rather than underspecified our preferences. Any suggestions are welcome!
This is a very personal preference, but if it were me and I were in your shoes (at least as I imagine it), I'd go to Proof and park there for the night. Wine, beer, and food are all amazing. Desserts are solid. I think the food is of the highest consistent quality. And there are plenty of other places to go in the area after if you wanted variety, but having an evening at Proof would be the respite I'd want.
1. Start at the bar at Rogue 24 (with an advance reservation). Have a few bites and drinks as you desire. When you want to do something lower key--but equally as aesthetically pleasing--walk a few blocks over to Baby Wale (should be able to walk in, but an advance ressie can't hurt). If you are still hungry, get a pizza. Otherwise, have a drink and their cookie dim sum.
2. Do a restaurant crawl through Cleveland Park. My suggestion would be start at Palena Cafe for a bite and a drink. Then I'd move to the bar at Ardeo Bardeo. Maybe a dessert there. You could add in Ripple (or Dino's before it closes!) if you want to hit 3 spots.
3. Alternatively, you could do a Barracks row crawl, though it would be a bit difficult on a Saturday given recent wait times (and no advance reservations). I'd start at the bar at Belga Cafe with some outstanding Belgian triple beer. Have some drinks until your table at Rose's Luxury opens (put your name in there before getting Belga). Have some bites and drinks at Roses. And then head for a night cap -- perhaps Sonoma or Beuchert's Saloon.
Anyway, these are the ideas that would top my list given your query.
I would head over to 14th Street.
I would start at Bar Pilar for a drink, then head to Cork for some small plates and end at Birch and Barley for dessert. You can't go wrong at any of these places.
You could always throw Kapnos in instead for the small plates, but if you stick to my above plan you will be walking up the street and not have to zip zag up and down the same street.
In Alexandria, you could do drinks at PX, Majestic, or Vermillion. Apps at Vermillion if you didn't do drinks there (even if you did, but I know you said separate places.) Not sure about dessert... can I say Vermillion again? ;-)