The fool managed to use his abundant energy to heal Dean's worst wounds, leaving him in a condition where he could, at least, move properly.
The boy wasn't sure if that man was his enemy or an ally, at first. However, after receiving such kind and easy-going treatment, he was more relaxed about that matter.
'Anyway, I must not leave my guard down. I learned through a tough experience that human kindness has a price. No one is nice without wanting something in exchange. That's how this world works, that's how humans act towards each other.' Dean thought as he sat in front of the fool, cross-legged like him.
Dean would glance at the dragon from time to time, but the latter wouldn't even give him a hint of acknowledgment for now. He didn't present any danger at the moment, but the boy thought that he should keep attentive about him as well.