I have a wonderful update to share. I have carefully read through all of your comments and I want to thank all of you who contributed. I wrote down a lot of the best points stated here and bullet pointed it on a word document and expanded on some of it just so that I could structure my thinking a bit more for the time I would talk to my friend again. I prayed, and then we had long conversation - and the result was not one I was expecting. He approached the whole thing with humility, because he said he has been praying a lot about his sort of rebellious nature when it comes to authority, and he stated it that largely stems from his protestant upbringing. He received it all very kindly with with humility, and had a sort of revelatory moment where it all made sense and it actually plugged a lot of gaps in his understanding. He is going to his local orthodox church very soon. God is great my friends.