There are a few things that are essentially Winchester, and even though up until this point, Glory hadn't met anyone on that side of the family, there are some things that just had to be a given. Like the bone-digging. And the classic music, which didn't make it into the story (although Glory's idea of "classic" is not quite the same as Dean's - her favorite classic artists are Eminem and 50 Cent, haha).
And you *know* that Dean would check up on them as much as possible without actually revealing himself. I see Glory as Dean's second chance - he raised Sam all by himself pretty much and then watched him from afar while he was at Stanford, so it stands to reason that he'd do essentially the same thing for Glory (though he was forced to stop after Sam got chewed up by the chupacabra in Idaho).
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There are a few things that are essentially Winchester, and even though up until this point, Glory hadn't met anyone on that side of the family, there are some things that just had to be a given. Like the bone-digging. And the classic music, which didn't make it into the story (although Glory's idea of "classic" is not quite the same as Dean's - her favorite classic artists are Eminem and 50 Cent, haha).
And you *know* that Dean would check up on them as much as possible without actually revealing himself. I see Glory as Dean's second chance - he raised Sam all by himself pretty much and then watched him from afar while he was at Stanford, so it stands to reason that he'd do essentially the same thing for Glory (though he was forced to stop after Sam got chewed up by the chupacabra in Idaho).