I definitely agree that you should push people beyond their comfort zones when you have some inkling that they are ready to listen. But I think you should be ready to listen to. Hussein seemed to be incredibly open and respectful. Since Hussein seems to be open to talk, there is a possibility to have really good, productive conversations. If a person, or if Hussein specifically, was not open than it doesn't matter whether the other person is ready to listen or not because nothing good can come from pushing their comfort zones. And when I say "open" or "ready to listen" I don't mean that they have to change their views. I just mean their has to be some sort of understanding, some sort of basic respect between the two people.
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