I did. She was part of an UBER UBER family.
I consistently dipped things to her - but in a way as to where I was confused, and or upset, or just not feeling right.
I kept telling her about disturbing things that were going on during elders meetings. I would be very open about how this stuff is not right and is hurting people.
I would point out the incompetent of many of the elders, and how our training is worthless.
I would point out the hypocrisy I would see.
I also had talks about how things didnt make sense. From things like masterbation being wrong, to why did God need 6 extinction level events before he got it right, to how the Flood could not have happened, and had to be a local event.
I pointed out how the bible makes a big deal about a woman not screaming while being raped (with no caveats to it - like her mouth was covered, or he had a knife to her throat, or no one was around) - but David and Solomon got to F#uch hundreds of women and it was ok.
How there was no chance that in Davids and Solomons harem - the girls were not having lesbian sex, and how David and Solomon were probably having group sex with there concubines.
I pointed out that a concubine is just a sex slave, and how is that ok?
Or when we had the reading about Balaam, that when a donkey started to talk, that instead of Balaam freaking out and running away, he stood there and had an argument with the animal like it was normal.
Or how strange that Satan really didnt lie to A & E, because at the end of chapter 3 God confirms what Satan said.
Or was there really only one way to get back into Eden? What was there a wall with only one gate? And why didnt their kids all continually try and get in sicce the tree ment live?
Or why did god introduce man to the FIRST weapon? A sword? Was that a good idea?
If he didnt want them to eat meat - why did he give them Furs from animals?
I talked about how scared I was when the WT put all the legal burden on local elders when it came to DFing and such.
I told her how confused I was that we needed to give all our Hall savings to the WT even though we didnt have a mortgage, and all the craziness about the LDC and such.
On and on like this over a long period of time. I was a prominent elder, not a "spiritual loose" :)
Eventually she did her own research, and woke up.