Yeah, I know I am sounding harsh. I have always been extremely kind and respectful towards this person. When we are together I try to appeal to his sense of humor. He has a great wit. So I try to make him laugh and I can do that. Sigh. I know I sound really harsh. I will probably end up seeing this person. You are right. I do gently try to bring him out of his bleak mindset. I do feel sorry for him. He is extremely intelligent and well-read and well-educated. I think maybe his arrogance might put people off. He is like a real life Grinch. Very lonely. I am certain I will end up taking him out to lunch - AGAIN. PS He knows he is a very negative person so if I told him that he would just say, "What's new?" -- I think I should just get together with him and make him laugh...which is what I usually do. But I have to be in a good mood for that.