Post(perfect)mates Delivery Date
This might sound crazy at first, but hear me out...
You and your date hop in your car with the Fleet App open, ready to pick-up food for lazy lunch-wanters. Pop on some music (Spin Doctors - Two Princes, is never a bad choice), and head out to pick up your first order.
On route, you and your date have so many built-in things to talk about (the music, the restaurant choices of the people ordering, why the person was too busy to pick up their own food, etc.)
I think it's funny to play "Dr. Delivery Driver" and do pseudo-analysis of the customer based on the tiny bit of information you have to go on. Make it fun, make it funny.
You can go one step further and have your date order thru Postmates so you can pick it up/deliver it to them!