Fun Crabs near Dupont Circle?
Its pretty much the end of Maryland Crab season. But for other crabs Bethesda Crab House complete with paper on the tables and pitchers of beer. You will need to call in advance to reserve crabs. It is several blocks from the Bethesda station on Metro's Red line, same as Dupont Circle. For seafood close to you try Hank's Oyster Bar, lots of recs on this board.
Virginia - the State that shares the Bay with Maryland - doesn't have a crab season. Watermen can take crabs year round and they do. I bought some local crabs this week.
That isn't much of a concern in reality because restaurants that serve the "local specialty" often get them from the Carolinas and the Gulf even in the Summer months because the supply is steadier and the crabs are larger. It's a little harder to find places that still offer them because the demand is down locally in Winter because crabs are considered a Memorial Day to Labor Day food in this area. October and November crabs from the Chesapeake are considered by many locals to be the sweetest and tastiest if you can get them. The MD commercial season ends 12/15.
Yes, despite your boss' wishes, I don't think you'll have much luck finding "fun Crab restaraunts close to your location. Phillips is an okay thought. What comes to mind to me as closest by is The Dancing Crab in Tenlytown. You could cab, or walk to Dupont Circle and take the Metro (only 4 stops).