Welcome dissonance!
I'm dating a baptized born-in. I came at him with 'questions' from all angles for a darn YEAR. Fortunately, I have the freedom to play stupid and I don't have access to the materials as JWs do so I could take full advantage of my ignorance to what I thought, was no avail. I'm now learning things seeped in.
Interestingly enough, in all that I threw at him, the darn eyelid opener was the evolution of the vaccination doctrine! He had been on me about getting my flu shot and I replied, "Okay. The fact that you're up on that doctrine's new light means a lot to me. Btw, what are your thoughts on how the WTS equated that with cannibalism? Can you imagine how it would have felt as an elder to have counseled a family who lost a loved on only to have the doctrine change later? It would have killed me had that happened to us." He was completely floored with that revelation.
I then provided him with this... http://jehovahswitnessrevealed.com/wp-content/uploads/2006/10/vaccine.PDF . *
I've learned something else. Part of his new angst is the fact that people on the outside of the organization have more information than he has access to and he's starting to realize the disadvantage he has. This poor man was reading that whitewashed history book and I suspect the whitewashing became evident so he put it down.
*As an fyi, I use JW facts and other sites to get my understanding down pat but to introduce concepts I use documents from http://jehovahswitnessrevealed.com/wp-content/uploads/2006/10/ and ask him to explain the quotes or the evolution thereof. It's worked wonders. After vaccination, I moved on to the evolution of the organ transplant doctrine. Once he sees and accepts the evolution of the former, he'll more easily swallow the possibility of the blood doctrine moving in that direction (which it already has).