Downtown
Hooters is good for eye candy for some but not my type. Most girls are there are in 20's.
Black bull has an amazing spot for outdoor patio to watch eye candy go by. Girls there are late 20's not looking to meet.
Some ladyfriends of mine in your target range go to shmooze Easy on 5th for the vary reason. However, they go after their own age group as they figured those men may be more 'successful' but deep down they are cougars at heart. So if thats your purpose, consider dress more mature, dark colour sports jacket or in suits.
In financial area, tons of bars targetting the Bay street type. Reds, The Keg on York, The old Traders Vic, many on front west of University Joe B's and others.
The ladies at 4 seasons bar around the time of Film Festival were definite hot. So are the ones going into Hyatt with hotel bars some are SP.