Cheese lover here. I don't post much, so refresher course: I've been dating an unbaptized JW for years. We're both in our 20s. He's not super into JWism and probably never will be because he thinks a lot of it is a pile of poo.
The problem is that he's scared to leave, for two reasons. The first is that all of the propaganda they spew makes him think all other churches are Satan's minions and that the JWs are still "the best behaved people who love God the most." I'm not sure how to ever dislodge that idea, considering the thought of going to other churches makes JWs think they'll burst into flame or something. Maybe he's afraid at my church, we have orgy Tuesdays. (Little does he know, it's orgy WEDNESDAYS. Tuesdays are human sacrifice days.) I get that he agrees with the core JW Bible teachings... mostly that Jesus isn't divine, there is no hell, and only "special company men who kiss lots of butt" go to heaven. Most people in mainstream Christianity have their own ideas of things, but JWs think free thought in church is more of Satan's minions and Smurf's work. So, there's that. He thinks all of the GB and organization stuff is crap, but he thinks he needs to go somewhere that's unanimous on tricky doctrines. (Which is just a sign of no one thinking or those who do think lying about it.) Basically, he knows the leadership is filled with tricky devils, but he still feels he must follow the tricky devils because they're the least devilish.
I think he'd be significantly more likely to jump ship, though, if it wasn't for the fact that he knows his circle of friends will disappear and that the family that's in probably won't give him the time of day if he left. As much as I tell him that his "worldly friends," his family that isn't JW, and I will love him regardless and not conditionally like the JWs, I know how much the idea of losing all of them kills him. It makes me feel almost guilty, too, because I know I'm basically the only reason he's confronting his doubts. I can't imagine the pain of basically losing most of the people who have "loved" you your whole life in one fell swoop. The organization is cruel and inhumane in that way. People do nothing wrong, they just wake up, and suddenly they're the devil.
I just wish this religion could be a more calm church like most others. Allow some free thinking and no shunning. Things would be a lot easier for its adherents. My heart hurts for my boyfriend throughout all of this. He's only really started being real with debating what to do for the past little while. He likes to shuffle it out of his mind a lot because it's hard being tugged all over the place, so it's taking him a while to figure it all out. He feels like a hypocrite and like God will hate him because he can't make up his mind. If he stays, he'll feel like God won't like him because he's being dishonest, but if he leaves, he'll feel he's left "God's people." I don't know how people don't just start talking to walls and eating paste in this religion.
If he actually decides to finally take the dip into the crazy train pool, it will be time to break up. Don't worry. I just really think he'll finally get the cojones necessary to ditch it all. I'm waiting and hoping he does. And so many kudos to all of you who have gone through all of this, escaped, and kept your sanity. (Or at least some of it... particles anyway.) I'm so glad my parents didn't get involved in a cultish religion. We had a very chill, liberal Christian upbringing. The only time my parents considered shunning us was when my brothers and I found ways to break the same pot that had just been fixed on a weekly basis when we played basketball. Or on every family vacation... ever.