I also remember a friend of mine who, though not being awaken, didn't believe in 1914 and many of the prophesies. He didn't believe in the faithful slave either! While he told me about this, I understood that he was still under the spell of : "Yeah, but look at all the good fruits the organization is bearing!"
On my end, I simply acknowledged that it was difficult to believe in everything and that we could choose to wait on Jehovah. That day, I didn't know if he was indeed fully awaken and fishing for my feedback, and I didn't want to risk anything. In addition, at that time in his life, he had various issues and becoming awaken at the same time could have proved to be "too much". Leaving the org is very difficult: losing friends and family, time to research and study and undo all the ideas that have been forced into you mind. etc. Some loose their marriage and other fall physically sick under the stress. I didn't want to add this burden on him in a time I knew he could not carry it.
Since I have become inactive, I have had a few conversations with him, however, we never talk about JW stuff. The day he will be ready, we'll have that conversation. In the meantime, I feel he is captive of his own mind and of his family.
Anyways... my point is this: Back then, when we had this conversation, I could easily have assumed he was awaken and this would have opened a whole world of trouble if I had done so.
This is why forums like these are perfect. We can reach out anonymously to people living the same things we are without the risk of causing additional difficulties to our own lives or of those that we care for.