You are going to the right city. It has an amazing nightlife - check out Ste-Catherines. So much to do. Stripper bars everywhere! Great city for hookers and blow.
Check out Buona Notte for good italian. Kinda expensive but is very high end.
If you want hip - Plateau Mont-Royal is pretty neat. There is also the area around the McGill campus which might be a little less pretentious.