Most Helpful Guy
I would go jeans because you can make a cute outfit with jeans and it's functional but a dress isn't really the best wear for the places you are going and it's not to functional.0
Most Helpful Girl
If the chemistry is there and if he is at least a bit daring, it won't be a friendly date, I can guarantee that.
You could try wearing a nice dress, but skinny jeans work as well0