I used to work with someone who was sensitive yet often made very wrong choices with her life, and it was easy for others to criticise or demonize her, and it got to her.
But I never did. I always offered sympathy, understanding and moral support. Even when she had stupidly got fired for turning up for work under the influence of drugs, and I hate drugs, but I still texted her (a few days later) to ask how she was. She told me, and thanked me, then announced she was pregnant. I could have been callous like "oh my God, why do you carry on making a mess of your life?" but I didn't. I just said "congratulations" and was supportive, because I guess that would be what I'd want people to say to me if I were in that situation, not to be criticised or shamed.
I'm that sort of friend, so it's ironic that I don't have many friends at all. Even the girl I was just talking about hardly keeps in touch, even before. She only texted because I texted her. I'm not the sort to bombard people with texts but I do show that I care every now and again and I like to offer support if I can.