The thoughts of a newly married, recently graduated, christ-seeking, pastor-to-be

Do We Grieve with God?

When I was in my teenage years I was something of a loose cannon in everything I did, good or bad. And sometimes I did things bad unknowingly and I could forgive myself of those things rather easily. However somethings that I did were bad, and I knew that these were sins, my personal choice to go against that which God has asked of me.
There were times when my choice to sin, and sin heavily, that when it was time for me to be alone with God I was sick, no real reason to be sick, but rather the sickness brought on by stress and anxiety. I would at the time tell myself that I deserved to feel sic over what I did and this was God convicting me of my sin.
How much more legalist could I get. Several years later I would really begin to comprehend the message of grace and love.
Now I begin to wonder of those moments where that sickness of stress and anxiety hit if perhaps, those are the moments when the Spirit, in triune nature with God and Christ, is grieving within, and I in turn am joining in with that grief. Not because I did something bad, but because I knowledgeably disobeyed my father knowing that there was no good thing ahead for me.
So my thought is this, when we sin, choosing to go against God’s commands, do we later join in the grief over those sins so that we better comprehend the grief that God undergoes when we sin. Not as a bad thing or punishment in this grief, but rather one of the few moments when God really meets with us to share with us.
Just a thought... Something to chew on.