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"Nearly a century old, this Georgetown institution has hosted every president from Harry Truman (booth 6) through George W. Bush and his family (table 12), and John F. Kennedy reportedly proposed to Jackie here in 1953—there’s a placard above the same green booth to mark it. Established in 1933 during the Great Depression and now run by fourth-generation owner Billy Martin, Jr., it serves comforting, leather-bound-menu American classics for brunch, lunch, and dinner and makes a great pit stop while shopping along Wisconsin Avenue. The frothy, fabulous espresso martini is done better than most ($17)—a neighbor with FOMO ordered one when mine came out. For heartier bites, petite crab cakes over fried green tomatoes, topped with poached eggs and house-made hollandaise, arrive with home fries and fresh fruit (market price); spoonable favorites include the best-selling beef chili piled with tomatoes, onions, and cheddar ($13.95), New England clam chowder that pleases year-round, and a piping-hot crock of French onion soup capped with baguette croutons that’s as gooey as they come ($12.95). During the holidays it turns into destination decor—fragrant garland, nutcracker soldiers, and tinsel wrapped around Tiffany glass light fixtures—while year-round the wooden bar fills with everyone from young moms sipping goblets of wine with bowls of fries to preppy locals on a two-martini lunch. Insider tip: bathrooms are up a rickety set of vertical stairs, where you can peruse old Washington Post write-ups and framed etchings of the original owners." - Tierney Plumb