Case by case basis. That's really it. You can metaphorically beat your head against a brick wall all you want in trying to " determine whether to show a jw the truth" as you put it, all day long. In the end, it is up to you to decide how, if or when. The other person 'the jw' in the case of this post, has to see for themselves. Or has to question things. But you said
I'm trying to express the conflict inside... Can anyone relate? -So, back to the subject.
This ^ .
That is the subject!
You are conflicted! She is not! That would largely explain the way you have been posting.
Relate? No.
I can relate to hoping they wake up, but that's not what you said. I personally would never outright try.
You said- I'm talking about someone I'm in contact with but who doesn't have questions. You also said-
I want them to see there is such a thing as a happy, friendly apostate.
You have answered your own question.
You said- I'm no longer religious about this "clinging to what is right" thing though, although I still care about authenticity.
Then just be authentic.
Your reaching for things that have no answer. If you pay attention to your thoughts as you are writing them here, you are answering your own questions.
Their is more at play in your mind than you are acknowledging or saying.