Dean gave a small nod before chuckling a bit, shaking his head as he started to pull away from Jubilee. He tucked his hands into his pockets before giving a small shrug. "Ruby's...Ruby." She's a liar. His eyes grow darker at the thought. Ruby was his last hope. And now? He lost that. There was no more hope there was just getting through these last four months the best he could and trying not to think about it. "She's useful because...she knows a way to save me."
And the lies go on. But at least he was instilling in her the hope Ruby was giving Sam.
He smiled a bit before starting to lead Jubes down the alley, looking for his necklace. Got his back. Yeah. We're pretty sure she didn't 'have his back' to any invisible forces that may prey on to shattered soul of the older Winchester. At least when the black out was happening because Dean would give a small gasp, choking down the light wisps before stopping in his tracks. Looking down at his feet for a moment before giving a soft grin.