Here are a couple of options:
Chinatown/Metro Center area. Tons of places to eat and drink, and accessible by every major line for convenience. Also close to the Chinatown and E Street theaters, which would give us pretty much any movie option we could want.
Cleveland Park. Again, good food and drink options, and the Uptown, should we decide to hit a movie.
U Street. Bars, restaurants, etc... Not as many metro options, and not as close to a theater, but closer to Dupont, which will allow me to get my leather fix.
I'd say Chinatown is probably the most convenient in terms being the easiest spot for everyone to get to, but I'm fine with whatever y'all want to do.