Drag Me Away (From You) tag
Dean's hanging on by a thread at this point and he's not sure how much longer he can deal with the shit that Chuck - the universe - is throwing at them. And he doesn't blame Sam for being pissed at the lies or Jack's plan but he doesn't know what to do. Cas came up with a plan that he desperately hopes will work but he (they) can't rely on it.
Dean wants to survive and hopefully retire but isn't sure there's a way out with Chuck bearing down on them and fucking everything else. Especially after he's destroyed literally every other world except for theirs.
It's killing him to think about Jack dying again but the kid's wrong that his death will make Dean forgive him - if that was the case, he would have killed him when Chuck wanted him to all those months ago.
So he'll lie to Billie and Sam if that's what it takes to make sure that Cas' plan doesn't get fucked over.
They're nearing the finish line and he's never been more terrified in his life. This is miles different from everything they've faced in the past. Team Free Will has a slim chance of winning, and if they do? Dean has a feeling that nothing will ever be the same again. And if they lose, the entire world's fucked.
The weight of the world is on his shoulders, something Sam and Cas also share the burden of, but he's falling apart at the seams. One wrong move or loss and shit's going to come crashing down on him, he can feel it.
The thread's snapping more and more each day and the weight is crushing him. Dean needs something to go right for once in their lives so the pressure can ease a bit.