Hello and Happy New Year.
As far as I know "to be friendly with someone" means to be friends with them. That (sort of) makes me think that "become" could sound better in this sentence: I tried to be/become friendly with him, but he was way too self-sufficient".
I see "being friendly with a person" as a state and "becoming friendly with them" as a process. I have no problem with "I tried to be friendly to him", but I'd probably choose "become" when it's "friendly with".
Thank you.
New words, one handy idiom, and a 2-minute quiz — delivered to your inbox to keep your streak alive.