What sort of places do you like, grant?
I think a casual and charming place for a date would be La Tomate at Connecticut Ave. and R St. (Dupont Circle neighborhood) Request a seat in the bar area, which is cafe-ish. Too bad it's not warmer out; they have a lovely patio.
There are several other nice, casual places right around there, too: Bistro au Coin, Sette, Thai Chef, Afterwords Cafe (attached to Kramerbooks bookstore, and has a separate little wine bar), just off the top of my head. If the date doesn't work out, you can drown your sorrows at Timberlake's bar, where my fiance used to bartend. Some floozy might pick you up, too.
