Sam had thought about talking to Dean sooner about what he did, but the other part of him couldn't when there was no open dialog with Ruby even. Clearly, he couldn't pretend to keep up the appearance of being okay. He was disheveled in other ways than just appearance. He had come to the bar out of a sense familiarity with the goal to locate Dean and he crosses it rather contemplative. He knew Dean was only trying to lighten his troubles, but he shoke his head. "That's the problem. Because of what I did, Ruby hasn't written back to me. I can't fix it here." Guess he has to spill, doesn't he.