I did try a clean break before in the past but he got upset when I said I didn't want to be friends with him and begged me not to cut him out. I'm trying to break it off but I don't want to hurt him. I think I'll just wait a bit longer when I feel up to him that I don't really want to be friends with him as he can't be trusted. I totally get what you mean about a clean break, but I also feel like I have to play the situation in a smart way as I don't want to get enemies either. Right now not thinking that clearly.