I say -- Don't analyze it, be grateful someone cares about you. Don't worry and focus on the deal details or if you ultimately succeed or fail.

I think the message he was conveying in this deal is the most important thing to focus on Pinksoil. To me he is telling you that he accepts who you and the things that you do. However he cares for you too much to let you to continue to avoid addressing this issue. Instead of telling you simply "don't do it!" he is trying to explore ways to help you diminish/extinguish this behavior.

Pinksoil I don't know what goes though your mind as you begin to actually cut. I would try to remember his caring and how much better it would feel to be chatting with him during your second session this week.

Good luck Pink.