Later, Sam and Dean take what's left of the spray paint and deck out Rufus's cabin with warding symbols of their own. Thus guarded against peeping angel eyes, they're free to wonder what the hell is going on with Castiel. "I told you something was off with him since he got back from Purgatory," Dean says. "You think someone's messing with him?" Sam asks. Dean scoffs at the idea that angels might be making him kill other angels because he's forgotten just what assholes 90 percent of them really are. But he does remember that Sam's not even supposed to be there. "You know what, man? I got this. You go." Sam is surprised. Dean says he's just tired of fighting. The scene could have ended right there, but no! "You know, maybe I'm a little bit jealous," Dean says. "I could never separate myself from the job like you could." He thinks it would be nice if one of them could be happy. Suddenly, though, Sam is feeling torn. Dean tells him he needs to make up his mind, but not in an overly bossy way. "Both feet in or both feet out," he says, because the show loves its parallels. "Anything in between is what gets you dead."
Sam takes a walk to think things over. Dean takes the opportunity to call Benny, who's sucking down a blood bag and looking like he'd rather have something fresher. He's relieved to hear from Dean, but it's not the good news he was hoping for. Dean thanks Benny for everything he's done, but it's over. He looks pained to say it, and why he's saying it is a mystery. Let's look at the options:
1. He's choosing Sam over Benny, as per Sam's ultimatum -- except he doesn't even know at this point whether Sam is staying.
2. He's shedding his distractions like Kevin did -- except it's not like every single case from now on is going to focus on the tablet hunt. Also, Benny isn't just a friend, he's also a supernatural creature, which kind of makes him part of the job by default. Not to mention, it might be handy to have Benny's help. He's a better fighter than Sam, right?
3. The show is contriving a scenario where Benny starts killing people again, leading to yet more Winchester fighting and angst.
You can probably guess which option I'm betting on, right? Anyway, Dean and Benny say their goodbyes, and they both look miserable, and they don't even get one last hug because they're thousands of miles apart.
That night, Dean sits in the cabin, looking thoughtful and sad as he barely watches a boxing match on an ancient TV. This, coupled with the sad music, is meant to make us think he's all alone, but it's Amelia who finds herself so. She shows up at the motel room and she's the only one there because Sam is at Rufus's cabin, cooking dinner. He and Dean give each other resigned looks and dig into their bowls of mystery slop in complete silence, far lonelier with each other's company than without it.