The revolving cycle was something that did need to stop.
It was just not going to stop here. Not right now. Dean knew Sam's mindset and he knew the place they were in the moment he had died. The tentative forgiveness Sam had given him for everything he had done before Metatron killed him -- it was a slippy slope. Everything they did was a slippy slope when it came to turning their backs on one another or hiding things. This was no different and that part of him that was saying that he should tell Sam was still nagging quietly. Then again, he didn't know Sam would react. He probably might just kill him. It was a logical concern in Dean's mind.
Not that was a bad thing. Dean knew how dangerous he was with the Mark. Even back home, he barely had control over it. It was leashing a great white shark -- sure, he was same old Dean most of the time. But when he got into it, it got dangerous. The fight with Rowena was a milestone for him, a success. He didn't kill anyone, he didn't black out and come back to himself surrounded by dead bodies so that was awesome. But that was the first time in the long line of massacres and overkills. He didn't even know what this place had in store for him, but he was hoping that maybe someone here had something that could help him. Hell, get the damn thing off of him even.
Because the last thing Dean wanted was to become that monster again.
Dean shrugged a bit as he finished off the rest of his beer and went to grab a cue, waggling his eyebrows a little. "Last time I checked his Jesus juice was on the fritz. He probably could get here and then what? Have him end up in the hospital? Not being able to help him? I don't think anyone in this place even knows how to fix an angel with no grace, Sammy. He'd die." Last time Dean checked, Castiel didn't have that many friends left up in Heaven either. Not any that would go to an alternate universe to pick up the Winchesters. At least Crowley would miss a feel-good conversation enough to maybe summon a portal.
He could see the guilt on Sam's face and he knew it well. It was the same feeling he had when he saw her. "Yeah, still...healing. Time works differently here, I guess? She got pulled right before she pressed the button. I'm staying with her at her place...when I'm not here because there is really nothing to do in this town. At all. Nothing. Get drunk and look for ways home." At least Sam was here now. That's the only bright side at the moment in his mind. Dean consciously avoided going back to the apartment and facing one of his bleakest regrets. He still remembered that night and he still felt a rotten twist in his gut.