Dean had been dropped multiple times into other realities, universes, or whatever you wanted to call it. But, this was the first time he had been greeted by a welcome committee, shown some incredibly ridiculous orientation video, and been handed a thousand dollars on the spot. Vallo. Some incredibly fucked up reality where magic was prevalent. There was another version of Lucifer running around, one who was supposedly not so bad, and then there was the one angel who seemed semi-decent, and who knew what other secrets the place held.
On top of trying to wrap his head around it all, Jo was here. The memory of her jumping in front of him to keep him from being attacked by a hell hound was something he had buried deep inside. The guilt over it had been eating him alive for so long. It had been years, and yet, after seeing her again, the memory was playing over and over in his mind. He could see it vividly, remember the horror he felt, the way she had sacrificed herself for him. It wasn't something he could ever forget, and now it was front and center like a corpse freshly dug out from a grave.
There was also Adam. Adam, who was currently attached to Michael, who might have been slightly less of a douchebag. Although, it was the same Michael who had possessed his father in the past and then erased the memory of him and Sam ever being there. Yes, Michael had healed his mother and brought Sam back to life. But, at the same time, he had also guaranteed that his mother would walk into Sam's nursery six months after his birth. Something that Dean had warned her about, begging her to remember and not go in there.
Jo had invited him to stop by for a drink, and at the moment, all he wanted to do was get wasted and forget. It wasn't too hard to find the place, and it looked exactly how he remembered it. Dean walked in with a smile, picturing Ellen behind the bar and Ash being Ash. The place wasn't too crowded, and it didn't take him long to spot Jo. She was still beautiful, and she hadn't aged a day since he last saw her. That time when she nearly killed him, though it had been through no choice of her own. "Hey, pretty thing, how about you walk your sweet ass over here and bring me a beer." He called out to her playfully in an attempt to ease the awkwardness he felt.