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Sneeky Dee's is a place I always end up getting drunk in Toronto (and have done since I was below the drinking age). Good bar tex-mex, but drink beer from bottles.
College St (from Bathurst east) is apparently the highest percentage of bars and clubs in North America? This may not be true, but someone said it was written in Penthouse or Hustler or something. There are a few good places.
Cafe Diplomatico used to be pretty good for pasta and coffee. Haven't been in ages.
There's a new bike shop that has opened up in Liberty Village. I stepped in and chatted to the guy when I was there last spring. He had just opened but seemed really cool and trying to make both a proper LBS, but had some nice bits as well. I'd love to hear how he's doing now.
Dukes is one of the bigger bike shops, with nice people. Urbane is a bit of a weird mix between BLB and Bikefix (if you can imagine such a thing!).