Dean swallowed deeply, feeling as though everything depended on his next few words...mostly because it did. Maybe Lilith was just fucking with Jo...but the nightmares he had been having lately didn't feel fake, and he knew that if he was honest he'd admit that they were more like memories than anything else.
"I tried..." his eyes were far away as he remembered bits of that horrendous ordeal. "I mean, it was hell, and I was prepared for that, as much as you can be anyway...I was cocky at first, and man, you should have heard some of the crap I came up with for those damned demons..." Dean smiled, remembering the moments he had been proudest of himself, when he had resisted the pain and told Alastair to stick his offer up his ass. He had done it for years, thirty long, awful years, and he was proud of that.
And just as quickly he remembered the day he had not been strong enough to resist anymore, when the pain and hopelessness got to be too much and he agreed, the day when he tore into the other helpless fools in hell because he had no choice. Had Castiel not pulled him out, he'd still be down there, ripping into those poor bastards.
Dean looked away from her. She couldn't know what he had done, how he had been forced to hurt those souls. "Thirty years is a long, long time. I did try, though, Jo...I swear to God I tried."