I am trying to think of solutions here rather than be a prophet of gloom. I gave that up.
You're last messages make this hard.The idea of looking at witness videos together makes the hairs stand on end. He does not seem to be mentally preparing to leave the witnesses. Rather the reverse.
He believes its the truth. Here lies the problem. I do not know if you understand what this means to a witness. That isn't meant to be patronising.
Catholic's, Protestant, Baptist have faith in Christ. They believe however that there could be alternative ways of worship - alternative ways of living that are acceptable.
For a witness there is only "the truth". And "the truth" is of couse, the truth.
There is no other way. No other acceptable option. No walking out without God's rejection and death. Outside is the wilderness,barren; full of danger. There's no hope outside. Only borrowed time waiting for Armageddon.
He believes this - after you're last few mails I see that.
His internal tape recorder spouts messages; the same ones, over and over. He does not really reason, he just hears the messages and reacts. He thinks he is thinking but its just years of indoctrination playing out.
"Its the truth;there is nowhere else;if I leave I will be destroyed". These continue again and again along with a million other messages. They make him feel guilty. They make him go to meetings. They could make him stop seeing you.
While this goes on there is something else - something inside - it is stunted,under nourished, pale and barely audible. It is fighting for breathe.It is him.
This is his true nature,fighting to be expressed. He struggles to keep you. Overpowered, supressed, trapped within a web of circular reasoning, false doctrine, unfair expectation. There is the organizations heavy hand pushing him down. There are the messages again,'the truth' is the truth is 'the truth' is the truth. He is losing concousness.
I know of people who have left the witnesses believing its the truth. I have known witnesses that have not been going on the ministry that believe that they will be destroyed at Armageddon.
A witness might say "I know God will kill me; it is his right and I probably deserve it."
Whatever he does for God, it is never quite enough.He must try harder, do better. He will never live up to such high standards. Such thoughts lead to disillusionment. This is when ones true self breaks the water for air and gains control.
It is a constant battle. Who will win?
Its strange but this war against terrorism doesn't help. Witnesses look to world events to guage the closeness of Armageddon.When they see such things they say "this is it". There's a rise in meetings attendance,field service activity.People like you're friend, panic and think its time to get with the programme.
Things are going badly for you. If the illusion were to be broken;If he were able to find out that the organization is not God's only mouthpiece - that it is one giant mirage; Then you might have a shot. But, that's a hell of a job and would take commitment and understanding of his religion which you do not have now.
I hope things improve, I really do.Be prepared though to face that this might not go as you hope.