I’m going to ignore the bit about your friend for now.

I have had the kind of conversation where you try to change someone’s mind. That is, distinct from the more common kind on the Internet where you’re just fighting.

It takes a lot of time and energy. You need them to see you as a member of one of their in groups, typically.

I have had a couple friends who would consume a lot of right wing media, but we shared some things in common. One was also working retail, both were video game nerds. I think because we had those things in common, they saw me as a friend, someone in an in-group, and thus listened to me.

If I had just sent them a YouTube video, they probably would have rejected it. If a stranger did, almost certainly.

Unfortunately, when I was no longer in their daily life they sort of drifted back to what their dominant groups thought.