The other night he said something to me like "I know you are less optimistic about this relationship than me because you never call me." So to me that seemed like he was feeling insecure and one-down and asking for reassurance. I thoroughly agree that my reaction which was to feel empathy/sympathy and want to reassure him is a sign of me falling back into my natural tendency towards a sweet one-down groove and that is why I asked you about it.
He's already pulling a whiny guilt thing on you and you haven't even MET yet? BIG red flag to me! Holy crap! I do not like the sound of this.
(I'm predicting your response to this comment of mine will be something like: "Well I guess I'm not doing a very good job of explaining the vibe. It didn't come across whiny at all, but fill in the blank," e.g., making excuses for him and rationalizing.)
I think you're absolutely correct that your impulse to respond out of sympathy was a throwback to your cow/rescuing/fixing him mentality. Follow your instincts on this stuff! If it feels icky, it is icky.
The fact that he's a captain of industry doesn't mean he isn't insecure. I dated a guy who was a decorated full bird colonel and chairman of the board of the organization I worked for, and he was emotionally about 12 years old.
