You can't handle the truth
I will say that I believe everyone passes judgment on people and their actions to some degree, but I guess I just tend to be more vocal about it than most.
My friends who know me well know that if they ask for my advice or opinion, it is entirely possible I may have some harsh things to say. But it rarely comes from a malicious place.
I strongly believe that people should not ask questions they don't want the answers to, or expect friends to sugar-coat reality for them. You're not doing anyone any favors by blowing smoke up their noses.
I mean, I am not a cold, heartless person. I've said the occasional "Yes, of course that dress looks cute on you," or "I'm sure he hasn't called because he's been busy," in order to be optimistic and not intentionally hurt any feelings. But I like to think being realistic and honest is best all around.
So what I have to say is this: If you're going to bring up a sensitive or personal topic in open conversation, you giving the green light for people to tell you their opinion on the subject.
Opinions and perceptions are very often misconstrued as judgment and I feel you're only 'judging' someone if you're holding them to your personal standards and faulting them for not acting accordingly. I try not to do that, but instead offer my opinion or give advice based on what I think is best for my friends considering their circumstances and personalities.
If anyone has ever said they don't want to hear my opinion, I am as respectful as possible and try not to bring it up or interject. The only exception is when I feel a friend is in a harmful or unhealthy situation. Is that me sticking my nose in where it doesn't belong? Probably. But that's how I do.
I guess what I'm trying to say is as long as you can gauge people's sensitivity and present advice or opinions in a respectful way, you're just being a friend.
Unwanted or unwarranted advice or judgment is what causes riffs and ends friendships. It's a thin line, so just be cautious.