Dean has spent all of his life following the tail of nightmares. They always slipped from his hold, helpless he had to see them dissolve until another one deserved more of his attention. For him, there's nothing if there's no horror, and when there's nothing, he comes to wonder how much of his life he has wasted in this, most of his time already gone.
He has never had a home, but his memories don't lack when it comes to base them in his most honest words, such a hard life that has doubtlessly left him with wise.
Of course, when seeing a sadness so settled in and almost indiscriptible, it is of concern, the one that makes you wish you could bring him peace and embrace his solitude with your sacrifice for him, a sacrifice to make him have at least one normal day in his life not worth of cries.
Every alerting feeling that hitches a panic upon him hasn't been healed by anyone else rather than himself. People can't ever understand that much of what he goes through. For him, there's always a reason and an explanation for his problems, but for outsiders, it might be a whole other concept he won't risk exposing.
"Please, don't drink," your voice interrupted his quiet crying. It wasn't even supposed to bring attention, Dean wasn't sobbing, and his shoulders didn't shake, but his face did give away the sharpness he felt at your comforting words in his chest.
For someone so close to another is easier to show empathy, but he won't have it if their feelings don't come up from the same memories as him. If so, no one could remotely understand him.