Gabriels Gate for dinner, cheap, good food, dark cozy atmosphere. Go walk the length of the catwalk at squaw island. Once you get past the shit smell from the sewage plant it’s great 
Leftbank is always nice, dinner is not cheap, but walk over to essex and get hammered for cheap.
Fort Niagara at night is awesome. No one is there most of the time. There is a hill you can look out the lake and see from Burlington to Oshawa, ON. The toronto skyline is awesome. The slience is deafening. You can fuck on the hill under the stars and no one will ever bother you. Bring a blanket
Ellicotville is awesome for dinner and drinks. Just don’t get too hammered it’s a little bit of a drive home.
These are all relatively mild things to do in the area because there really isn’t too much going on other than parks and nature stuff.
Things I like to do depending on the girl are
walking elmwood, going for a long drive and just talking or playing karaoke with random radio stations that’s always a blast if you can’t have fun you got nothing, Toronto, go to allen and bar hop, hate on people, people watch…then hate, look in the artvoice for whats going on for that night and pick something fun. Usually a good show or event going on. If the event turns out to suck, just hate on everyone. Nothing brings 2 people together like picking out the flaws of others
One thing you are leaving out here is what does she like to do? If you don’t know then make a date where you can just hang out and get to know her. Make sure that you don’t give off the friend vibe. Flirt with her, who gives a fuck, if it doesn’t work out it doesn’t work out but it’s a good time regardless. If you are not slightly aggressive your gonna get the friend card fast. Trust me lol. I have had alot of practice in the last year and a half some good some bad.
Do things that make you happy first. If your having a good time it’s usually easier to give off a general vibe of a good time.
In the end it’s all a learning experience so treat it as such. Then there is no bad outcome.