Their relationship is so weird:
1. Trump really seems to have respect for Tim Cook. You wouldn't expect him to say "Ah yes, he actually makes good points, I'll think about it"
2. It's weird that from all business leaders - it seems that Tim Cook is the one who has the closest relationship with president Trump. In many ways he is the "Anti Trump". I can't help imagining Cook thinking "what an idiot" everytime they meet.
3. What if they actually are friends? That would be an even stranger relationship of a political leader and a celebrity being friends than Kim-Jong Un and Dennis Rodman.
For disclosure: I'm European and while I find Trump irritating, I wouldn't call myself Anti-Trump (nor pro-Trump).
I've never met Trump but I've heard he's very charming and charismatic in person, not at all like the persona he puts on for crowds when he's having a one on one conversation. Although I didn't vote for him and don't support many of his policies, if he invited me to dinner (in a context other than fundraising) I'd go, just as I would for any other US president, and I'd expect it would be an interesting evening. I don't think Cook was thinking "what an idiot" throughout their conversation.