It kind of sounds like he needs a sense of humor. I think I've mentioned Im going to become a therapist and it may just be my laidback nature, but if I had a client say "yeah its because you love me" I would probably just make a joke back, I wouldnt get all offended or weird about it. Also with the not wanting you to hand him the check, it sounds more like that may just be his own issue. Like not wanting to shake hands. Next time he doesnt rise when you leave, you could say to him: You know it is impolite not to rise when someone leaves your company. Also regarding the angry email you recieved, he should know better then to think that it takes courage or is admirable to send someone an angry hate filled letter. Next time he defends someone who has hurt you, come back with "Do you just enjoy the fact that people hurt me and want to encourage that behavior, because your reaction is sick!" Call him on it right when he does it. He works for you, you pay him. You wouldnt put up with an employee treating you that way, dont let this guy. It may just be his personality, but he still needs to be called on it. You could tell him "Im going to record the next session and then play it back for you so you can hear how hateful you can be" Tell him he's a good therapist, but he needs lighten up. A therapist shouldnt be that easy to offend!!