IIRC, in grey canon (the journal screencaps), he had the boys with him on visits to Missouri, and Dean actually talked to her, back when he wasn't talking to anyone yet.
Didn't Missouri say she had met them? Dean was a funny looking kid etc.
I am going to have to replay this Mary scene a lot, I think.
Okay, this is the scene that really works well if you assume that Dean has always gone back to 1973. It's the way she looks at him and says his name, not so much like greeting her kid, but like greeting an old friend.
One last hunt, Mary. One last hunt.
"I'm sorry..." but she still doesn't tell him what she's sorry for!
Oh, nice. Bad-ass Mary, even back in S1. "You. Get out of my house. And let go of my son."
Okay, right there, she's apologizing for making the deal. I would lay money on it.
I guess I thought, "I'm sorry" at the time meant about Jessica. But there was so much more.
"I'm sorry."
"For what?"
Oh.
Oh, I think I'm going to cry.
Didn't Missouri say she had met them? Dean was a funny looking kid etc.
Yeah, but it's not clear if she met them or saw them via John in the show.
And the "why would she do something like that" scene is even more of a killer now.