What Is The Loving Thing To Say?

I hear conflicting advice as to what is the loving thing to say to someone when they aren't making the right choices.

Is it better to vocally question their behavior? Or is it better to not address their actions at all?
Do you draw a fat line down the middle or blurry the edges?
What choices should you address and which ones are better to be left alone?
Honestly, I don't have any of those answers.

But in at least one circumstance Jesus interacted with a woman who had been married several times and currently lived with another man. In crossing culturally normal barriers, with even his disciples questioning him as to why he would be talking with her, he took time to briefly get to know this women. In their conversation he made it clear that he knew everything she had done. Yet the love he showed her was so evident that when he offered her living water, instead of responding 'how dare you condemn me?,' she went back to town and told everyone about this man she met at the well.

Listen to a modern day version of this story (which is also found in John 4). I am still processing this story and especially the line in the video "to be known is to be loved and to be loved is to be known." Jesus' example here is that you can both speak to people truthfully and have them know that you love them deeply? There is something powerful about being known and loved!  Now I just have to figure out how to do the same...