As stated in the title, I have been raised an atheist, and while I have a relatively open mind, I do not currently believe in a god. My best friend, who I met six years ago, is a Jehovah's Witness. I believe the reason he has been allowed to be friends with me is because he didn't have many at the time we met, and his parents wanted him to be more social, but we've kept in contact ever since.
Over the last year or so, I've done some research into the organisation he is part of, and I have been lead to believe that it is generally quite hypocritical and has many cultish (using Hassan's definition) tendencies. What he believes the organisation to be does not line up with what I have read about it. I'm sure all the reasons I have to mistrust the organisation have been said a thousand times on this forum, so I'll just assume readers know what I'm talking about. I do not wish for him to waste away his life serving a group not worthy of his time. He already hasn't gone to College, despite definitely having the smarts and ethic for it.
My question is: how do I go about de-programming him?
You can understand that I'm in a precarious position: as a worldly friend, I could quite easily be construed as under the influence of Satan, and should the elders or his parents catch wind that I'm trying to wake him up, they would almost certainly force him to cease contact with me. I would much rather fail at awakening him than lose him as a friend, so I'm being cautious.
At the moment, when the topic of his JWness comes up (which is fairly often given how much time JWs spend on the organisation), I respond in a supportive manner, never encouraging his practices, but always happy to ask him about it (eg. how was your witnessing this morning, that cake you baked for the seminar looks great etc.) Is this a bad thing to do? Should I make my position more clear so that I don't accidentally steer him further into his faith?
Aside from passive comments, we've only had one active conversation where I questioned his beliefs in my best impression of an epistemological conversation. I phrased it as my own questions, not me undermining his beliefs, and it went fairly well, but I haven't brought it up since because I don't want to push my luck.
Does anyone have any experience in this sort of situation? Have I been going about this the wrong way so far? Should I slow down, or push harder?
Thank you for any responses you may have.