Squirrel Hill Cafe AKA "the Cage" can be a good time. This is primarily a student, hippy, hipster, old regulars, and local randoms who live near here spot. They sell decent priced pitchers and broadcast the games. It does get incredibly packed at times.
A solid neighborhood bar where you can sit at the jukebox and pick the tunes you feel like head bopping to. I always end up putting something on like MGMT or Florence and the Machine, I get weird looks when a soulful jazzy soprano starts belting into the room. I'm usually in my own world at that point but you have to love those "you can find any song you can think of music machines" I sure do!
I like pulling up to the bar next to a young college bloke and ordering two fingers of bourbon neat, that's always an eye opener from the Punky Brewster girl with the mouse voice sitting next to you. The bartenders are attentive and so are the servers when you are sitting at the tables.
There is an upstairs room but the ceiling is crazy low, must just be made for the Shawties! I really like that the booths have such high backs so if you are having an intense conversation you can hide in there!
One last thing, this is a smoking bar so if that bothers you don't visit, your clothes will be reeking by the end of the night! Cheers!