He straightened up in his seat and looked over at Jesse. While he wasn't thrilled with the City, he'd also seen just how happy his brother was here. He didn't like the idea that this would be yet another thing that Dean would lose.
He took another healthy drink from the beer bottle, mulling things over more. The weirdness of the fact that he was sitting with someone who was actually God wasn't lost on him. It seemed almost petty to expect someone with Jesse's powers to take an interest in him or his life or even his brother, and yet here Jesse was.
"If it's going to happen, is there any way that you can make sure that Dean goes back with Dinah when it does?"
Bringing her to their world wasn't the idea option. She could handle herself possibly, but their world had a whole lot of death and loss and Sam thought that maybe Dean would be better in Dinah's reality. He just really didn't want to see Dean lose someone else. He didn't even know if this was something that Jesse could or would do, but he had to ask.