I guess the best question is where in the city do you want to be? Downtown, NW, SW, SE?
If your looking for a kensington Hangout Sam's Deli off of Kensington Road is one of the best dive bars (easy going, no pressure of popum and circumstance). The Hopinbrew pub is also a good place off of 1st street (as long as you don't go on a night when the emo kids take over).
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