I agree with what people have said & he doesn't sound Luke a good guy. Listen to them. However, on the flip side, can I ask you some questions? I am currently dealing with a friend, and yes I know she has some issues and I fully support her and her issues. But sometimes, its like all she can do is complain. The mean dude she ran into, work hassling her, her landlord and howww much she hates living where she does (but refuses to look for a different job or place to live). Sometimes I make an innocent remark and off she flies just complaining and I gotta say.... I'm pulling away. So great job on boundaries, talking and therapy and working hard at your job. You're probably be better off & happier without him. Let the trash take itself out. But when you say your negative feelings have nothing to do with him, even if it's nothing negative about him, he is the one listening and it might just seem like a comment here and remark there. But trust me they add up. I've left events because its just endless whining and moaning and nothing ever is possibly happy or even neutral and must be constantly complaimed about (for hours...) and well yeah. But yes better off without him.