(Re)Understanding Sin

So I've been fighting with Hebrews 2:17-18 and Hebrews 4:14. When I read these passages I can help but think "How could a holy God be tempted in the same ways that I am? I (when left to my own devices) am wretched and filthy and evil. He is beautiful and pure and good. How could his perfect and beautiful mind have ever held the thoughts that enter mine every minute of the day?" I suppose I'm fighting against these scriptures because they go against my initial understanding of God from my formative years: A loving and yet somewhat judgemental God who loves me and wants the best for me but really has no idea what the world is like these days. An "out-of-touch" God who can't relate but tries to in lame ways...sort of like the father of a teenager who uses expressions like "hip" and "groovy" and "wicked" trying to connect, but in actuality just reinforcing how disconnected they really are from the world today. I don't believe this anymore (at least I hope not)...but old habits die hard. It's difficult to reprogram...it's a process...it may take years...or a lifetime. Scripture (which I believe is truth) tells me that I have a holy and perfect God that knows every sinful thought in my mind...he knows my wicked heart in a way I never will and not only that...he understands. He doesn't condone. He doesn't wink. He doesn't except my sin as inevitable. But he understands the context of my sin. He knows the condition of my own heart better than I do. He understands my situation and the culture I live in better than anyone. My sin is much more real to him than it could ever possibly me to me. To me it may be a source of shame and remorse...momentarily. To him, it was the cause of ultimate humiliation, and unimaginable pain.

How could he still be God and be tempted "in every way" like me and you? How can he know the depths of my depravity and still love me? I'll probably never fully grasp the answers to these questions. I do know this: when I look at myself I see the grotesque disfigurement of sin. Somehow, when he looks at me he sees only the beautiful countenance of Christ. May what is real to him become real in me.