As they head deeper onto the thickly wooded island, Dean takes out his phone and composes a message for Sam. "Hunting vamps -- nest on Prentiss Island... not alone." Dean is awesome for bothering to use proper capitalization in a text message. Benny looks around and asks, "Remind you of anything?" It's almost as if the Purgatory scenes were shot in the same woods! Dean deletes the message without sending it. He and Benny grab their weapons of choice and talk about how weird it is being back in the world. Benny seems to find it all a bit overwhelming. "Hell, I don't even know if this world is real -- if I'm real," he says. Dean stops in his tracks. "Listen, I've seen what's down that rabbit hole. We're real. This is real. That's the only way to play this game, you get me?" Benny doesn't say anything.
It turns out being a vampirate pays really, really well. The Old Man has quite the elegant colonial-style mansion. You'd think he would have a security system of some sort, but Dean and Benny just walk in through the back door. They skulk around inside, finding it oddly dark and quiet. Benny gets distracted by the sight of the Old Man's harpsichord. Beside it, there's a framed photo of a young woman with dark hair. Benny picks it up and mutters, "No, no, no." He takes a shaky breath. There's movement on the stairs above him. When he looks up, he sees the same young woman staring back at him. "Benny?" she whispers. "Andrea," he says. He's so stunned to see her, so relieved and so sorry all at once, that he can't move when three men move to surround him. He offers no resistance as they brutally beat him down. Dean, hiding around the corner, hears the whole thing. "Idiot," he whispers.
Benny comes to some time later, handcuffed to a chair. A youngish, dark-haired man holds Benny's Purgatory ax to his throat. "You're gonna make me do this all over again, aren't you?" he asks. "Hello, Sorrento," Benny greets his murderer. He looks up at Andrea, who's standing in front of him with her arms crossed. "He turned you," he says. She nods. Benny looks sadder than ever, even though her confirmation was only a formality.
Meanwhile, Dean is prowling around the house, slipping easily back into predatory mode. His focus is only broken when by his phone vibrating in his pocket. He looks at the phone, sees that it's Sam calling and shoves the phone back into his pocket. Dean sees a shadow up ahead and ducks into the nearest room. A vampire (presumably) peers down the hall before walking on.