I think part of the reason we hadn’t shared a flight before is is simply a lack of communication and misunderstandings. I won’t nag him, or anyone, to come flying and he won’t pester me to take him flying. So, outwardly it looks like I’m not too keen and that he’s not too interested; neither of which are true.
“Don’t you have to get permission from ATC or someone?” That’s the most common question I get when people discover I launch myself into the sky from a field. Confusion then turns to disbelief when I tell them “nope.” I usually let that little pot of incredulity simmer for a while; sometimes I’ll stir things with a “why would I need permission?”