Perhaps we really are long lost twin sisters the Tesseract separated at birth. :)
The fact that you're aware of it in some ways makes it easier than if you were to believe it can be evaluated once and then will always be. If you surround yourself with good people then you have someone to hold up the mirror that helps you see yourself more clearly.
No, but calculation requires a certain amount of understanding of what is to be calculated. And I've known him for less than two years, and only a few months of that with any knowledge approaching intimate. You don't have to answer, obviously, but how long have you known him?