Of course he would, I'm his family.

[ Jack is only realizing now how many things he took for granted. He's been safely tucked away into a cocoon of sorts thanks to Castiel and Sam's reassurance of him, loving him even after being soulless and having made several violent errors of judgment. He's been privileged to have that sort of support, and he sees that now that it's gone. He has the surety of a child with absolute faith in his parents, and he wonders if he was wrong. ]

We had the bunker though, and we are hunters, so we don't have real jobs. I guess I'm lucky we never had debt before.

[ Not that he was aware of before. Jack only thought about money when Dean would hand him some in order to get them groceries. Otherwise everything was just sort of provided for. He's becoming more and more aware of how sheltered he is, and has to come to grips with that without those safety nets. ]

I think he'd like the motorcycle, if he is here, I can't wait to show him.

[ One of Jack's most important life goals is to impress Dean. ]

Well nothing is like his Impala, it's special.