[ The way Jack listens to Benny talk to Dean is arrested, focused, and there's a longing in his gaze. He's always known Dean a very certain way and he's never gotten much of the warm and charming side of him. He tried his best with Jack and he went as far as he could, but for all the love Jack has for him, it's never been as sincere between them. Not since he died the first time, before he lost his soul and ruined their relationship for good. ]

I'm glad that he had that. That both of you did. It must have meant a great deal to him. He ended up making other friends of people who he'd ordinarily kill. Maybe he learned from you.

[ He wonders what happened to Benny though, that Jack's never heard of him. He thinks he knows most of the Winchester's friends by now, even if only spoken of in passing. He knows of Jodi and Garth and Charlie obviously he met in Apocalypse world, but he's heard of their version too. But not Benny. With Dean it could mean a lot of things, but Jack has been closely observing him for the three years he's been alive, and he wonders if the silence comes from pain.

Not that he's going to come right out and guess that Benny is dead in some timeline, but Jack has a feeling. They all die eventually, the lives they live. He knows that better than most. ]

I have some money. Maybe we can buy a blood bag? I'd make them do it but ... I'm not supposed to do that again.

[ Jack's reality-altering is a power that caused some serious trouble for the entire world, and part of why his father turned on him, understanding that Jack was more powerful than him. He can make a lot of things happen if he wants it to, but it wouldn't be right. They can do this the mercenary way. ]

We can try at least, right? I'm not going to let my father's friend starve.