If you asked the angel now, after everything they've been through, he would say that trying to make sense of ineffable things is a fool's game. And he's been that fool for eons.

He smiles fondly. Sweetly. Calmly at him, for how ironic that might be, coming from someone like him. Shyly, over such examples of affection.

He brings his other hand up, freeing it from Crowley's, just so he can touch the other side of his head as well.

"... I think, perhaps, we should revisit the idea of resting." A casual way to say he'd like the demon to get somewhat closer to peace.