So S, answer the filing for the extension and leave it at that for right now.
Then, get out of the way.
You keep pressuring him with lists and questions and what to tell his parents, whether he wants to end it or not, etc. When you do that and he says he doesnt know, its because = HE DOESNT KNOW!!! By you continuing to ask him, you are forcing him to come up with an answer he might not really be ready to give and you are not really ready to hear.
Sweetie, just live your life, do your thing, let him blow in the wind. He needs to figure this all out, in his own time, in his own way without any noise from anywhere else. Let him.