Having procured all the information they need from Hell's Wimpiest Crossroads Demon, the Winchesters motor on to an unnamed city. As usual, it's a rainy night. Perhaps there's a raincloud that just follows the brothers around wherever they go. They approach a cab driver waiting outside an alley. "Ajay, we need to talk to you," Dean says. "You know my name," Ajay says, a bit surprised. "And what you do," Sam adds. Did the crossroads demon give them a picture of this guy? Point him out on his Facebook page? Because how funny would it have been if Sam and Dean had gone on about needing to go to Hell and then it's the wrong guy? The episode doesn't have time for that, though, so the Winchesters are lucky enough to track him down on the first try. They explain they want to cross into Hell. Ajay thinks they're nuttier than Aunt Martha's pecan pie, but agrees to help them for a price. "You two are resourceful," he says. "One day, you will owe me a favor." The brothers are surprised that the guy knows who they are, even though everybody -- supernatural or otherwise -- should recognize them by now. But this is all just an entree for Ajay to explain that he's the Reaper that took Bobby Singer to Hell. The brothers are incredulous that Bobby would have wound up in Hell. After all, it makes no sense! It's cheap! It's an all-too-convenient revelation just when they happen to need to find an innocent soul in Hell! Naturally, they weren't counting on the brilliant writing from the same team who brought us the dog lover episode. Anyway, Ajay blames it on Crowley's machinations. "All right," Dean says, "how much for two tickets down and three back?" He just told you the price! God! Sam pulls Dean aside to argue that he needs to be the only one to do the trials. Never mind that Dean might be a handy tour guide, having been there himself for several decades. But the writers don't want to remind us of that much better foray into the infernal pit, and so they don't.
Sam goes back to Ajay for a single ticket. Dean's a bit wary, but Ajay explains Sam will be back in "exactly 24 hours," even though we've been shown before that time doesn't work the same in Hell. Ajay leads Sam into the alley while a homeless man watches with interest. He's apparently been standing there the whole time, and nobody thought to lower their voices when talking about reaping and Hell and the like. The alley dead-ends into a showcase of graffiti, leading Sam to look around in befuddlement. "Take my hand," Ajay says. Sam does so while muttering, "And it gets creepier." Like out of everything he's supposed to do, holding hands is the thing that gives him the heebies. The earth rumbles a bit and the graffiti smears towards a painted door that is a bit reminiscent of the TARDIS from Doctor Who. The door gives way to a light that expands to encompass both Sam and the Reaper.