It was when both my children came to us, at different times, and were in tears because they were frustrated that they had no real friends, neither "wordly" (because I was trying to be a "good" JW) or at the Hall (because they just weren't reaching out to *us* despite us reaching out to *them*. Because we weren't very active in field service and not "regular" at meetings). They felt very alone.
It broke my heart. I determined that I wouldn't let them go on like that.
A few years later, they have friends, everything has normalized, and the wife and I have faded with no regrets. When you get a little distance and perspective, it really is amazing how much BS you realize you put up with. And how hypocritical the entire Society is.