Downtown Places:
Bymark - upstairs, you can see it from the TD courtyard and entrance is off Wellington on the north side. Drinks are expensive but there is a lot of eye candy. Thursday and Friday after work are best. The Restaurant downstairs serves a nice Kobe burger that will set you back $30.
Canoe - TD bank tower, 54th? floor, it is labelled in the elevator or ask the security desk. Most afterworks are busy, Thursday/Friday are very busy. Mostly "industry" people (Bay Street types) and is also very expensive. You have to get there early if you want to sit near the bar.
Jump - I would avoid and many people do, is it still around?
Chocolate - King Street East across from George Brown ... a 20s type crowd with a great happy hour. Thursdays/Fridays are packed right after work with a somewhat Asian crowd.
Crocadile Rock - Duncan/Adelaide - go for Wednesday 911 nights later on, lots of MILF material. Laid back and jeans allowed.
Easy on 5th - Thursday/Friday after work is more of a corporate get together place. I usually go later at night and there is some good action from 20/30s types. Most Fridays and Saturdays this place gets very crowded.
Hughies - well at least it used to be called that and many people still do. On Front west of Yonge beside Sushi place. Thursday/Friday are best. Many workers from BCE seem to settle here.
Loose Moose/Armadillo - Front west of University, good on Thursday/Friday but can be hit and miss.
Schmooze - already mentioned.
Black Bull - on Queen west, a nice patio come and see my HOG type of place. very laid back and good deals on pitchers.
Milestones - on John, beside Hooters, nice patio and Bellini's or the inside bar. Actually in this small stretch there is Montana's, Al Fresco's and a couple of other small places on the other side. During Molson Indy they close this portion of the street and have a big party.
That should give you some homework for the next little while.
Enjoy,
VBB