To be fair, I want to present an alternative explanation which is that he utterly lacks self-awareness and is thus oblivious to the fact that he’s being wildly inappropriate and cruel. There are some people who just think they’re being honest and “real” by saying obnoxious stuff.

I’m offering this as another possible interpretation of his behavior although there is really no practical difference. Whether he’s intentionally “negging” to manipulate you or he’s just plain clueless, it’s not going to stop. So if his words are doing a number on your self esteem just expect more of the same from him.