[ Dean is a protector once he gets emotionally invested in someone and while it took him a little while with Jack to get over his prejudices, he got there. They may be on uncertain terms, but he doesn't doubt that Dean does care for him, and has loyalty to him. That's all he could ask for after what he did. ]

Yes. It's complicated, but it's true. They've been very kind to me.

[ They were supposed to kill him and chose not to. Dean wanted to in the beginning but when he had a gun to his head, he decided not to. Their a messy family but they are at heart, and Jack is so grateful to them and everything they've done for him. He is proud to be a Winchester.

He is very curious about this man though. It doesn't matter that Dean's never mentioned him because his fathers are notoriously bad at telling him anything about the past. They are very focused on the present and the future, and they've sheltered him about their experiences. Not to mention Dean in particular is closed door on his relationships and his feelings, so Jack wouldn't expect to be told about a friend that he helped from Hell. That sounds in line with the sort of adventures they had. ]

Well ... it means you are free then, isn't it? You're here instead of there.

[ This place may be strange and not where they belong, but it's not Hell or anywhere else bad. ]

I'm Jack. I'm always glad to meet a friend of my fathers, are you a hunter as well?