Well if he's a good boy and it sounds like he is, let him fly. If he screws up then you reel him in ..I would also give him a new Curfew. If his Curfew was say 11:00 on foot, then in a car it should be 10:00 . My kids are far from driving but I have thought about this alot...also I like the one friend plan, just one friend in the car makes it much safer all the way around Good luck !! keep us posted please