He looked at Sam strangely over the mention of Adam being so much more chill than when they had met him the first time after he had been resurrected by the angels. "Yeah, well, he-" the kid had just been brought back from the dead by angels, something he had never known to exist before. On top of that, he was being used as a pawn and manipulated into doing exactly what the angels wanted. Adam had been so young and completely naive to the supernatural and it only made sense that he had been upset. Did Sam think this was the Adam he had left behind in the cage not long ago, or maybe, did he not realize that this was the Adam he had shared a cage with? Was he completely unaware of the fact that Michael was with him?
He took a long pull from the bottle and set it down on the table with a heavy sigh, both hands rising to rub briskly at his face. It felt strange to Dean that he found himself to be much calmer, not ready to fly off the handle at any given moment. It was probably thanks to Vallo and not having to worry about saving the world from monsters. He felt much more relaxed and maybe he had mellowed out a little with age. "Yeah, Adam is pretty great." He agreed with a nod, a smile on his face as he recalled their time spent together the past few weeks. Hopefully, they would soon be things they could all do together, as a trio.
He wasn't too surprised when Sam expressed hesitation over Alec, but he knew that wasn't the real Sam. He would come around, he was sure of it. "You can take whatever you want, Sam. I don't really know if the shirts will fit or not, but you can still try them on, it's not a problem." Dean was starting to get the feeling that this time around, Sam would be a little more difficult to manage. He was in a strange place with an older brother was unfamiliar to him, Mary was alive and well and so was Adam. Honestly, he was surprised that Sam hadn't already lost his shit. "Yes, Sam, you still have good hair in the future, don't worry." Questions like that made Dean feel a little more confident that his brother wasn't lost entirely and he looked back at him with a smile.