I didn't know Capitol Hill like others--played pool and watched football in the basement of Zack's, by myself or with a woman. Occasionally would order a pizza upstairs along with $2 pitchers, which were small but good for at least two beers. Occasionally would go to Cap Lounge and play pool with the lobbyists. Mickeys was my other hangout--now long gone, and probably so is Mickey. Little Pub was the last of the pool hangouts and the old timers, now mostly gone. Henry's and Bullfeathers are still there, but don't expect fine dining, and so is the Monacle. Also the Ugly Mug on 8th, is a few doors down from where I used to live.
Bombay Street Food on 8th street in Capitol Hill: really spicy, try Lamb Vindaloo, otherwise Lamb Korma is great, Chicken Tikka Masala, ask for extra rice, split a Taj Majal, or drink a full bottle. Pizza, maybe try Matchbox for personal sized pizza, Belga Cafe or Carusos Grocery for fine dining. Trustys is a good drinking bar and the psychotic bartender used to work door at Pour House or Cap Lounge, and there's Duffys on H, along with The Vic for soccer, the Pug (one of the owners used to work at Cap Lounge) is great for artists, late night wtf mini Emo's is Jimmy Valentine's Lonely Hearts Club, this should get you started.
Texas Exes meet at Penn Quarter Sports Tavern to watch the Sugar Bowl (South of Chinatown).