wordplay

I think you can't help feeling disappointed if that's how you feel, but that's not the same as feeling you own the person or are being too judgmental. You can totally respect your friend's freedom and know their lives are up to them and still occasionally tell them if they've done something you thought was beneath them. Of course some people cross that line into where it really isn't their business or where they're not being appropriate. I mean, like, if a friend is telling you you should have taken a job you didn't want or shouldn't divorce your spouse when you think it's a right thing. That's going to cause problems. But being a friend is a give and take and I'd think it's assumed you have some expecations about the other person's character.

If you don't care at all what they do one way or the other, that's not always a sign of friendship. Sometimes it just means you don't care. To take an extreme example, if your friend is addicted to drugs are you a better friend to just not care or to be someone who says, "Hey, I'm not going to tell you what to do but it's upsetting to me to see you doing stuff I think is harmful to yourself."