He rolled his eyes a bit as he pocketed the flask of blest water and taking out the colt pistol that the black eyed skank...he totally meant Ruby, had fixed for them right. The older Winchester checking the bullets and paying attention to Jo all at the same time before his blood ran cold with realization. Jo didn't know. What had happened to the Roadhouse. To Ash. Jo would notice that 'I'm a badass hunter with everyone in the world kept at arm's length' expression crossing his face as he licked his lips and put the colt away.
Did he really have the right to tell her about everything? To tell her what Ellen should be telling her? That once again their home was taken away from them? That the little makeshift family they knew was gone. Up in flames like everything the Winchesters got close too. Dean's life was filled with death and the ashy remenants of what could have been. Jo didn't deserve that. No one did right now.
He took a deep breath, running his hand through his short hair and turning away from her. A sight Jo would know quite well. Regardless if he wanted her to know or not. "...The Roadhouse is gone, Jo. The Yellow Eyed Demon burnt it down before Sammy got killed." Which, Jo should know...the younger brother was still alive. Hopefully she was smart as she was pretty and put that together without Dean having to explain it.