Most Helpful Girl
Putt-putting is a cute, classic first date. Some friendly competition is always fun :) another idea that I think is really cute is going to one of those cupcake shops (if you have one near you).
Here are some other random ideas:
Hiking, and eating sandwiches/lunch at the top while enjoying an incredible view.
Most Helpful Guy
Somewhere where you both enjoy and where you have time to talk and get to know each other better!!