Take her to true confections. I have taken all my first dates out here and its great. Alot of people around talking, so she doesn't feel awkward . ( ive dated chicks where they find it weird when its too quiet )
http://www.trueconfections.ca/
Cakes tastes awsome and they give big portions .Get her a float or a shake. WIN WIN
And after that 3 blocks north and there's a starbucks so you can swing by and get her a warm coffee so you can walk together while holding something .
I usually try to take the date around 7 ish while sun is out ( summer ) so when you finish your cake date around 8-9, the warm coffee / tea feels nice and the lineups in starbucks isnt too bad.
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I try not to bring dates to nightmarket, mall, PNE because i think there is too much of a risk of meeting your friends/her friends and if they say something stupid ,it may cause an awkward moment.Plus, you end up trying to dodge the crowd more then your focusing on her. I carry a work phone as im always on call so dodgin crowd + work emails would mean that you dont' get as much talk time.
its your guys' time, after all , its a date
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Some things work for people and some don't . but at the end, just find out what shes like and that will determine where you can bring her.