I would offer to pick him up after you finish up your evening w/your friends and if he doesn't want to wait on you, he can find his own way home. You are giving him a choice to make of his own accord. However, whatever you do, don't change your plans.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.
