I always agreed with this friend. He and I used to work together. We had a great time. He moved away but we were friends.
The FB comments are all pretty irrelevant "oh hey, how have you been doing?!" except for the one pictured. This is a friend and a professional colleague - someone I usually respect. I'm not ready to burn it down yet, because I think he and I can have a rational discussion, and I think I could actually change his mind or force him to think harder. He is a gay man - one would think he'd be sensitive to this stuff, but as we've all realized, just because you are an oppressed class in one way, doesn't mean you can't be an oppressor in another.
I want to respond with the following but wanted to let you guys see if I am on point, or if you'd add anything:
The thing is, it's not up to white people to decide this, period. Blackface has a long and sordid past - one that white people of today don't remember that well if at all, and certainly have never been victimized by. If we don't just err on the side of caution, we're just as bad no matter our "intentions." If you dress up in black face, not intending to demean black people but knowing that it will offend and hurt black people, your intentions turn into "IDGAF about your feelings." And that makes you a pretty big asshole.
You can defend anything with "intentions." You can drop the n-word and say you were using it as a joke; doesn't change its effect on those victimized by it. You can fly a Confederate flag with the intention of displaying your southern heritage, but it doesn't change its effect on those victimized by it. By doing one of these things and knowing they will offend people, your intentions have turned into willful ignorance at best.
Here is the linked article, for reference. I get it - she was dressing up as a specific person. But she didn't need to paint her face to do so, given historical context. She is not going to be HARMED by forgoing the blackface, or not dressing as that character.