"Dean, where are you going?" Sam knew better than to follow Dean if space was what he wanted. They could talk more later if need be. He looks at Dean equally as surprised when he returns with the whiskey in hand, wearing almost the same expression of surprise and what the hell as before. "Dean, listen. If there was any other way I knew, I would try it first. I don't know how else to ease into telling you. You know where lies get us. I thought I would just be honest from the start." He shakes his head as it's not possible to return to Madison or Jess. He had his chance with Jess when he first arrived in Heaven but the two of them had grown to be different people in opposite worlds. Jess would always be in his heart, but not come close to Ruby. He nods accepting those terms from Dean. "Alright. But I'm limiting you to a few hits a day. Anyone in their right mind would be scared of you if they didn't know you."

"Once I reach Ruby. That's the other half of this. Right now there is no set time frame."