What a sad and familiar story! Like so many others, I ended up here after befriending a JW. I spent an embarassingly long time ignoring the warning signals and trying to write off discouraging behaviors with my penchant for quasi-tolerance in religious areas.
Finally, after hearing one too many uncharacteristic comments from my JW friend, I started poking around on the internet. I was blown away by what I learned. I also started reading some books on cults, specifically on dealing with people who are in cults and decided that after quite a lengthy amount of time together that I would not forgive myself if I did not try to loosen the control of this group over my friend. I slipped things into conversation, I encouraged actual thought process, I encouraged questioning but without making specific reference to his group. I threw in information on other groups. I read a variety of Witness resources so that I could better understand the arguments I'd face. I argued online with active witnesses (before being unceremoniously dumped from a website or two!) I was armed with info and ready to go at a moment's notice. I walked carefully, inching along, hoping that I could raise just a few nagging doubts or capitalize on some existing ones without pushing my friend away. I really tried. But, I lost my friend.
Ummm, here's the unusual part...
then, after almost nine months, my friend came back to me saying he wanted out of the group. I knew he had been disfellowshipped during the interim and that he had kept up with meetings trying to get back in. So, it came as a bit of a shocker when he called me out of the blue to meet up with him.
He's still got major issues that need to be addressed. He still thinks it's his personal failings that make thr group wrong for him. It doesn't occur to him that the group itself could do anything wrong, per se. But he's been "out" physically for several months now. I know he still has a way to go in really setting himself free but I've decided not to push for the moment.
I love my friend. I love the person that he is. I didn't like the person he was when group-personality took over. You could see he had two distinct personalities working at the same time. Genuine and group personality. Frankly, he's a warm, non-judgemental person so affiliating with a group that considers those qualities something of a weakness would never be a good match for him.
I'm sorry for the pain you've felt. I can relate. Best of luck!