Helping others? Listener question

I'm seeing a person I care about struggling. Seeing the world as against them. Playing out the patterns of their childhood. There are urges to point out where this person is getting things 'wrong'. And maybe to be their 'saviour' even.  I see that ideas of me...and them are all over this ...

It's confusion. For sure.  

Starting here,  I can look to the ways that I do this? Does this mean not challenging the thinking of others? Ever? I want to ask if it's wrong to try to share the things this conversation has shown me (even though I know that question in itself containx the confusion)

The confusion is suggesting to me that this whole dilemma is created from the idea of self and other