Dean was sitting at the bar, drowning his sorrows in a beer. Well, his third one, actually. He had a lot of sorrows to drown.

Ruby had gone off to find the Impala, and meanwhile Dean had hopped a Greyhound to NYC. It would be harder to track him in an area as filled with people as it was here, which is what Dean needed.

When the singer sat down next to him, Dean lifted his head. "Give her a drink on my tab," he told the guy, then flashed her a quick smile before going back to his beer.