Dean's seen the healing thing before - Cas managed to mend his broken fingers after he'd thrown a punch at his shadows and snapped a few bones with the force. So yeah, while it is kinda douchey that he sit back and allow Castiel to fix up Phil's leg when Phil would obviously rather be chewing glass, it's better this way.

And he feels like that poor kid in elementary school who just wants all his other friends to get along. Dean throws a fond smile at Cas as the angel finishes up.

"Relax," He claps Philip on the shoulder, "Now I don't hafta carry you. Can't have you bleedin' all over the place, anyway."

Speaking of which...He looks down at his hands, grimacing. Slick with red, Dean rubs as much off on his pants as he possibly can. "Let's, uh- Let's get back to the Tower of Terror before anything else shows up in here. This place ain't exactly a den of happy memories, if I recall correctly."