you should come down end of the month for Caribana, I'm surprised no one has mentioned this. When you come, make sure you get a hotel D/t, don't bother staying anywhere North of Bloor, it will take you too long to understand the transportation system. There are a lot of hotels in the core, you can walk to any even, or quick cab ride.
Things to do:
Check out jays, TFC, Molson Indy, some concerts, club district - too many things to do here, especially if you stay d/t.
As far as the women...hmmm, all I can say is this, know your league. Girls here try to act very pretentious, but again, its contingent on where you frequent. So if you attempt to approach a high class looking girl in a high class club, you'll prob get shot down if you don't look rich/really handsome, or have something about you that sends off an intriguing aura. This is true if you attend a club like Muzik. But again, clubs aren't the only place to get women. If you have a NY/Southern accent during caribana wknd, you can eat really good.