The vibe reminds me of all the stars i’ve loved by glorious_spoon, a futurefic drabble which was written almost a decade ago (during the Summer of 5x22), which I will always remember, and which I think about more and more as S13 progresses.
Jack has experience of the Winchesters as story, and is interested in story (he watched Star Wars, which is actually a great way of thinking about how Jack things. Episodes IV-VII are epic, archetypal, character-driven tales; Rogue One and Episode VIII (The Last Jedi) are very much not—they’re ensembles sifting through a world spread so vast and a war executed so differently that legendary beings and cults of personality don’t operate in the way they did). It’s the stories Jack invests in, and uses as models, and keeps in his mind in contrast to the Spire Cone World and Michael, etc.
Of course, it’s not like Jack doesn’t have personal experience of Sam and Dean, in addition to narrative experience of the Winchesters. But that makes me think—maybe he doesn’t. Maybe on some level, that’s what it means to be nephilim. He’s lived with Sam and Dean but maybe his perceptions of the world are just different, and humanity is something he receives in translation (even if springing grown from Kelly’s womb made him appear to be tabula rasa). It’d be interesting to listen in on him and Castiel discussing humanity as a second language, so to speak, especially since Castiel has learned such an ecelctic, regional dialect of humanity and on speaking more with Jack he might also discover that they’re not operating from quite the same set of perceptions and assumptions, either—because an angel and a nephilim are not the same; because one who has lived since Creation and one who has lived since Last May are not the same; because they understand Star Wars differently. Because any number of things.
But even then, maybe as nephilim Jack’s perceptions are more given to cosmic scales than the average, well, Jack. He loves nougat and values individual life but in order to pull the fabric of worlds together, open rifts, access power—all of it requires fluency in the cosmic, and the cosmic can’t help but color how you see things. (Dreamwalkers are tools with which to enter other universes, but they’re also the closest thing he’s ever seen to himself. More than other humans. More than angels. More than monsters.) So he knows Sam and Dean, but in a way very particular to nephilm.
I'll bet Jesse struggled with this, too. And no amount of careful socialization, parenting classes, and child theory could really make up that difference for him--not until he got a little order, and was put in a position to understand his own POV and why it's different. To see the frame of his own story.