Kramer books in dupont is a bookstore/cafe/bar that is independently owned, as is politics and prose a ways NW of Dupont. E st cinema (metro center) and Silver theater (silver spring) do fun movie events all the time, but I'm not sure about "independently owned".
Amsterdam Falafel in Adams morgan is great, sweetgreen is a local salad chain, 2 amys is an amazing pizza place, district taco has vegetarian options (those are reasonably priced, at least for DC). Yelp is incredibly active in this city, so that in conjunction with happy cow will do the trick. If you want upscale, Zatinya (greek tapas), Restaurant Nora (all organic restaurant), Rasika (upscale indian) are verrrrryyyyyy tasty, but super expensive (but if this is a work trip with reimbursements, go for it).