"According to your plan, the world loses you, and me -I- I lose you too, and that is unacceptable to me, Dean. Unacceptable. Totally."
Bonus:

seen from India
seen from United States
seen from China

seen from United States
seen from Finland
seen from United States
seen from China
seen from United States

seen from Philippines

seen from United States

seen from United States

seen from Singapore

seen from China
seen from Argentina

seen from Pakistan
seen from China

seen from Malaysia

seen from Malaysia

seen from Malaysia

seen from Argentina
"According to your plan, the world loses you, and me -I- I lose you too, and that is unacceptable to me, Dean. Unacceptable. Totally."
Bonus:
i know there's been lots of talk comparing the behind the building begging for help scenes in 1.09 & 13.01 but what really gets me is that in both instances, dean is asking someone who's already said basically said, "you're not supposed to need (my) help. your job is to help others."
1.04
This is John Winchester. I can't be reached. If this is an emergency, call my son, Dean. 785-555-0179. He can help.
11.23
DEAN: What about us? What about Earth? CHUCK: Earth will be fine. It's got you...and Sam.
and yet...
1.09
DEAN: Dad? I know I’ve left you messages before. I don’t even know if you’ll get ‘em. But I’m with Sam. And we’re in Lawrence. And there’s somethin’ in our old house. I don’t know if it’s the thing that killed Mom or not, but… I don’t know what to do. So, whatever you’re doin’, if you could get here. Please. I need your help, Dad.
13.01
DEAN: Okay, Chuck… or god, or whatever. I need your help. See, you– you left us. You left us. You went off. You said… You said the earth would be fine because it had me… and it had Sam, but it’s not, and we’re not. We’ve lost everything. And now you’re gonna bring him back. Okay? You’re gonna bring back Cas, you’re gonna bring back Mom, you’re gonna bring ‘em all back. All of ‘em. Even Crowley. ’Cause after everything that you’ve done, you owe us, you son of a bitch. So you get your ass down here and you make this right, right here and right now. Please. Please help us.
DEAN DOES NEED HELP! THIS SHOULDN'T ALL BE ON HIM!!!
"he's evil" and he just sitting here like that
just a... a replica. "incapable of holding life." (14.18 "absence")
omg i never considered jack attaching himself to dean because he was trying to grieve his mom and cas just like dean was.
I think it might be one of the things going on in 13.01-13.04, though it's not just that. It's also that Dean is honest, while Sam hides ulterior motives for why he was being nice. Jack's dislike of lies is a throughline all the way to "Moriah" where he makes it impossible for people to lie to each other. And I'd wager Dean specifically lying to Jack about the mal'ak box wounds Soulless Jack the most, because the truth is something he depends on Dean to give him the most, in situations where Cas or Sam might handle him with kid gloves he doesn't want. I also think Jack and Dean just have innately a similar sense of right and wrong and both care in a way that makes Jack gravitate toward Dean.
But yeah. Dean serves as a model for feeling your feelings, whereas we don't see Sam's numb exterior crack until 13.04 when he shouts at Dean over Mary. Not only that—Jack specifically overhears Sam minimize the significance of Cas's death in 13.03, which Dean fiercely rebuffs. Jack makes it very clear in 13.01 that he considers Cas to be his father, and Sam has become so emotionally detached that he convinces himself Cas death doesn't even matter. Dean fucking cares about Jack's dad, and trying to grow close to Dean is also probably a way Jack thinks he can feel closer to Cas! Dean's emotional outburst at Sam's dismissive language in 13.03—among other things—makes it clear that it's okay to miss Cas, and in that very moment, Jack calls out for his father and wakes him up.
Supernatural, 12x23 "All Along the Watchtower" & 13x01 "Lost and Found" // Victoria Chang, from "The Beach, 1964", With My Back to the World via weltenwellen
13.01 Lost and Found