These are great points,GK. One of my issues is that I have had so many good intentions twisted that I get frustrated when that happens and adding frustration to the mix isn't helpful. I will try to be more mindful of how to validate his feelings when he does misinterpret that.

Start with being mindful of yourself. If YOU are feeling frustrated, that will come out when you attempt to validate. If you are feeling compassion for this guy who was never validated as a kid, and is looking for the invalidation he's used to everywhere, your tone will be right.
Great advice, Grey Kitty. And Notwendy, I completely understand how frustrating it is to have one's "well meaning intentions twisted." And when it happens and I've tried to explain, he digs his heels in and just becomes more convinced I'm being selfish or judgmental or some other completely wrong motivation. So now I no longer JADE, but it still burns to think that he's misinterpreted something positive.