Keemstar's interest on Wings is... kinda weird, don't you think?
He's not the same with Boogie, as far as I'm aware. I think both speak on more equal terms, but Keem seems to treat Wings like some kind of retarded younger brother? With Phil, his interest is more of disgust and genuine interest of how someone can be so unlikeable while not playing a character.
I feel like Keem has a soft spot for Wings since Wings helped him to grow up back in the day. Someone who knows Keem will prove me wrong, but I don't recall him giving advice to someone as Daniel Keem rather than the Keemstar persona, even if both overlap.