Good questions....I'm wondering what the book would say.
I sort of am leaning towards putting the best foot forward, most positive light, blah blah blah....Because even if you DON'T mention the hard stuff, he knows you. He'll know it was there. And if you're not telling him about it, he'll feel the detachment. It's what he wanted, after all, but now he's wondering...is it?
So - show him the best you. The one that initially made his head turn.