I’ve often said that Season 7 convinced me of the canonicity of Dean/Cas, and to this day it boggles my mind that so many fans blame Sera Gamble for “ruining” the characters’ relationship. So I thought I’d step through my favorite season, episode by episode, and point out exactly why I’m so convinced their love is not only of the romantic sort, but also very, very canon.
The next trio of episodes mostly focus on Bobby and the boys, so the emphasis here isn’t as much on Dean’s grief explicitly as it is on the nature of father-child relationships. Still, there are a few moments worth digging into, and I’ll even go so far as to argue that the A plot (Bobby’s death) is meant to be a mirror for the C plot (Dean’s grief).
But be forewarned: We’re getting into some Serious Sads territory here. Keep a tissue handy, and remember, as Rufus says, the only way out is through.
9 – How to Win Friends and Influence Monsters
The elegant thing about the Leviathan storyline is how its premise reflected the nature of grief. The Levis look normal but really aren’t; which mirrors the fact that Dean looks normal, but really isn’t. It’s only when you can see inside, past the masks and illusions – as Cas can, aptly enough, for both the Levis AND Dean – that you realize how awful and wrong everything really is just under the surface.
Still, from the outside, Leviathans look like everyone else, as so do those struggling with grief and depression, and it’s actually one of the main reasons I love this season so much, because how often do you see a mainstream, pop culture phenomenon like Supernatural tackle something so subtle and complicated as human grief, and with such sensitivity, too?
This all comes to a head in “How to Win Friends and Influence Monsters” (another Edlund episode!). Let’s start with Dean says under the influence of the Turducken:
Dean: Are you kidding? I’m fine! I — I actually feel great. The best I’ve felt in a couple months. Cas? Black goo? I don’t even care anymore. And you know what’s even better? I don’t care that I don’t care. I just want my damn slammer back.
This is the first time we’ve seen Dean be able to name, out loud, in words, what’s been eating at him. And it isn’t Sam’s mental illness, or losing Ben and Lisa. It’s about Cas.
Specifically, it’s not about Cas’s betrayal, or even his stint as God, but about “Cas” and the “black goo”, the two ideas together, hand in hand. That means Dean is specifically referencing Cas’s death here, given that Cas died by from the black goo inside him exploding its way out (another example of internal, unseen forces ripping apart the external, ‘healthy’ shell. Are you starting to see the theme for this season yet?)
Now that the Turducken has severed his connection to his grief, Dean is finally, finally, able to look his behavior in the eye and put words to it, and it has Cas’s name. That’s huge progress. Huge.
For what it’s worth, Bobby and Sam exchange extremely worried glances after Dean says this, and as Dean sleeps off the Turducken in the van, the two men have (what I believe is) their first and only conversation about Dean’s mental health in the entire series:
Sam: You don’t worry about him?
Bobby: What do you mean? Before the Turducken?
Sam: Yeah. I mean more, like, ever since my head broke, and we lost Cas. I mean, do you ever feel like he’s going through the same motions, but he’s not the same Dean?
Bobby: How could he be? .
Look, I’ve had this exact conversation before. Word for word, except for the bits about Cas and the Turducken. And this is not a conversation you have about someone you love who’s lost a friend, or even a family member. This is a conversation you have about someone you love who’s just lost the most important person in their life, the person who once gave their life meaning and order, their reason for living. This is a conversation you have about someone who’s just lost the love of their life.
On a sidenote, notice that Sam doesn’t really blame Cas for the destruction of his Wall. He only mentions it here as a way to acknowledge Dean’s initial emotional loss of Cas (that preceded the physical loss), rather than as a way to express any spite or hurt over the action itself. This is confirmed in the next exchange, as Bobby asks Sam how he’s doing:
Bobby: Aren’t you full up just playing Snuffleupagus with the Devil all the live long?
Sam: I don’t know, Bobby. Seeing Lucifer’s fine with me… Look, I’m not saying it’s fun. But to be honest with you, I see it as the best-case scenario.
You’ll also see this sentiment echoed in the conversation Sam has with Cas in “Reading is Fundamental”, where he has the opportunity to rage at Cas, but instead only expresses concern over his friend’s mental state. Because for all his arrogance and anger and other mental problems, Sam owns his pain in a way that Dean never learned how.
Which is basically what he says in the last part of the exchange:
Sam: I mean… (presses hand) …at least all my crazy’s under one umbrella, you know? I know what I’m dealing with. A lot of people got it worse.
Sam is obviously implying that his brother is the one who has it worth, as we saw in “The Mentalists” (and as Sam learned from the final scene), Dean’s crazy isn’t something he knows how to deal with. Heck, months later, and he’s only just been able to name it. No wonder Sam’s worried.
Later in the episode, Bobby expresses fatherly concern over Dean’s mental state, a continuation of the conversation they had in “Meet the New Boss”:
Bobby: How’s your head?
Dean: Well, I think the slammer’s pretty much wore off. In between that and the 20 cups of coffee, I’m nicely tense and alarmed.
Bobby: I wasn’t talking about that.
Dean: (visibly tensing) Oh, Bobby, don’t go all Sigmund Freud on me right now, okay? I just got drugged by a sandwich.
The language Dean uses here is important. Dean’s not afraid that Bobby expects him to talk about his feelings (else he would’ve made a ‘couples counseling’ or ‘sharing and caring’ crack, as he did in “Meet the New Boss”). He’s afraid that Bobby wants to psychoanalyze him; that is, to interpret and pass judgment on what Dean feels.
And what exactly is Dean worried Bobby will analyze? The one big secret he admitted to while stoned – that he can’t cope with Cas’s death. Now that the Turducken has worn off, Dean’s once again afraid of the labels, of putting the name to his grief.
I’ve talked many, many times before about how Dean struggles to reconcile who he is with who he thinks a man should be, which is an outdated concept mostly handed down to him from his father and reinforced by the hyper-machismo Hunter culture. “Man” versus “Me” — this is the prevailing conflict in Dean’s life, and it’s dominated his story arc since Day 1.
Dean clearly thinks his grief is unmanly, that it’s a weakness that shouldn’t be expressed (thanks, John Winchester) and thus why he tries so hard to hide it from everyone, especially his closest family members. Dean’s terrified of how weak, how unmasculine his grief makes him feel, which is why he overcompensates by clinging even harder to his machismo than ever, especially when pushed by his family members. It’s why he pushes so back on Bobby here.
When it becomes clear, however, that Bobby wants to talk about his new “party line” about how “the world’s a suicide case: we save it, it just steals more pills”, Dean breathes a visible sigh of relief.
But Bobby isn’t letting him off the hook just yet:
Bobby: I’ve seen a lot of hunters live and die. You’re starting to talk like one of the dead ones, Dean.
Dean: No, I’m talking the way a person talks when they’ve had it, when they can’t figure out why they used to think all this mattered.
This is also a pretty huge moment, Dean admitting he’s lost his purpose in life, and his connection to why any of this mattered. I mean, he’s said “I’m done” before, and “I’m tired” and all of that. But this is something new, something distinct. This is a man giving up.
As we know, Cas brought Dean back from Hell for a holy mission from God, and I think hearing that he was special, that he had purpose — that message was so unbelievably important for Dean, and part of him never really let go of it. As long as Cas was around, there was tangible proof that Dean made it out of Hell for a reason; and that his life had meaning.
But somewhere along the line Cas began to represent something more than just divine intent. He became divine love, something worth protecting in his own right, something worth fighting for. He became family. And now that Cas is gone, that tangible reminder of the cause Dean ordered his life by (as Meg would say) is gone too.
Bobby realizes this is a big moment too, though his reaction might be at first hard to understand.
Remember back in “Meet the New Boss”, I pointed out how exceptional it was that Bobby offered to discuss Dean’s grief? Well, in the next few lines, Bobby reverts to his usual mode of denying Dean his grief and pain – but this time, he takes the time to explain why he does:
Bobby: Oh, you poor, sorry… You’re not a person.
Bobby: Come on, now. You tried to hang it up and be a person with Lisa and Ben. And now here you are with a mean old coot and a van full of guns. That ain’t person behavior, son. You’re a hunter, meaning you’re whatever the job you’re doing today. Now, you get a case of the Anne Sextons, something’s gonna come up behind you and rip your fool head off.
Bobby makes explicit something he always (wrongly) assumed Dean just inherently understood: That it’s not that the pain Dean feels isn’t valid; it’s that your pain can be used against you. That’s the nature of the job. Bobby’s message is harsh, but it isn’t unkind. Anything but.
When you lose yourself in grief, Bobby says, the solution isn’t to just suck it up and not feel; the solution is to find your own purpose, your own way out:
Bobby: Now, you find your reasons to get back in the game. I don’t care if it’s love or spite or a ten-dollar bet. I’ve been to enough funerals. I mean it. You die before me, and I’ll kill you.
That bolded sentence might seem like a throwaway comment, but it really isn’t, especially since we know this conversation is all about Bobby acknowledging Dean’s grief over Cas’s death. By offering that Dean find purpose in “love” (meaning, love for the memory of those he’s lost) or “spite” (revenge for the memory of those he’s lost), Bobby acknowledges that Dean did love Cas, as well as the conflicting emotions Dean still feels over Cas’s death. He doesn’t deny Dean’s feelings, or tell Dean not to feel. He merely tells Dean not to let his grief be the death of him.
That should have you pumping your fist in a “Fuck yeah, Bobby Singer” moment, because seriously, do you think that John ever would’ve said something like that to Dean?
For what it’s worth, Bobby’s words leave Dean speechless. The joke he follows up with about “condos” doesn’t even really make sense in context, and it’s really just a distraction for Dean to process what Bobby said. His face softens. His shoulders relax, ever so slightly. Maybe Dean is even finding some measure of comfort in Bobby’s words.
I love that Bobby and Dean had this moment before Bobby died, this touching moment of “sharing and caring”, because Dean always listened to Bobby’s advice, and Bobby always knew what to say so Dean would listen. And considering Dean’s about to spend the next several episodes getting terrible advice from authority figures, I love that this genuinely good advice is here, because hopefully it means it’s always somewhere in the back of Dean’s mind.
10- Death’s Door
I know I might get flack for this, but I think the idea of killing off Bobby wasn’t a bad one. In fact, in retrospect, I rather like it. And I say this as a card-carrying member of the Bobby Singer fanclub! (So don’t flame me, please!)
But Bobby is a crutch. He is the brains of Team Free Will, the go-to answer man, the one who does all the hard work of thinking and analyzing, and Dean especially relies on him too heavily, at the expense of his own intuition and intellect. For Sam and Dean to truly come into their power as adults, you need to remove their crutches – because in a Heroine’s Journey, you need to lose the things you think you can’t live without in order to unlock the power you always had inside you all along. (Before the finale, I wrote a five part series about how Dean’s Season 7 storyarc is a Heroine’s Journey, which you can read here, here, here, here and here.)
The problem is, Bobby had existed so long in the SPN universe, and cheated death so many times, that we’d as an audience begun to assume he was off-limits. If the writers were going to kill off Bobby permanently, then they probably should’ve done so back in the lead-up to the end of Season 5, when it would’ve made sense as a way to raise the stakes for the Lucifer/Michael showdown. That he should come so far, and die now, almost felt cheap, like the writers had betrayed our trust. And then once we factor in the canon-bungle that was Bobby’s return… well, we’ll get there when we get there, I suppose.
Still, now that I’ve had time to get used to the idea, I actually don’t feel so hurt about it, and I see his death as a necessary stepping stone in the Winchesters’ journey. Parents die, so that their children can inherit the earth. It sucks, but it’s a natural part of life. It was Bobby’s time.
Okay. So. All that aside.
“Death’s Door” isn’t really an episode about Cas and Dean; it’s a love letter to Bobby Singer (as well as it should be. Bobby deserves it. Because did I mention? Bobby’s awesome.) And yet, “Death’s Door” is also a prime example of the A plot mirroring the C plot, because Bobby’s story is a reflection of Dean’s. There’s a reason all the father-son bonding moments shown in this episode (such as the playing catch scene) center on Dean, because what Bobby learns here directly foreshadows the lessons Dean will need to learn to move past his grief.
The point of this episode is that the way out of death, be it literal or metaphorical, is to face the stuff you don’t want to face head-on, without flinching. The only way out is through the door you don’t want to open:
Rufus: You gotta go deep… Deep, like, crap you do not want to think about, so you bury it, you shove other crap over it, and you don’t go there, ever.
(That’s classic Heroine’s Journey stuff, by the way. Whether it’s Rapunzel or Hawke or Inanna or whoever, a Heroine always learns that that the only way out is through.)
This, of course, directly mirrors what Dean must do in order to come to terms with his grief. He can’t even face the memory of Cas’s death in his dreams – remember how his nightmare in “Shut Up, Dr. Phil” was shot in that strange, jerky negative space? – and the only time he can name the source of his grief is when he’s so stoned out of his gourd that he forgets how to feel. Eventually, to reconcile this thing devouring from the inside out, he’s going to need to face it, head on, or die trying.
Another mirror occurs after the scene where Bobby and Karen have the fight about his not wanting children.
Rufus: So, how long after this…
Bobby: …did she get possessed? Three days. Biggest regret of my life, this fight. You’d think it was when I had to stab her to death, but… no. All through that… I was thinking we never got to get past this. If I’d have known, I’d have said anything she wanted to hear.
Why does Cas’s death sting Dean so badly? It’s not just that he’s lost the love of his life (which by now I hope I’ve proven Cas is; but if not, well, just wait for “Repo Man”, because goddamn). It’s that they broke apart at the end of Season 6, and Cas died before they were ever able to repair their relationship. When Cas died in “Meet the New Boss”, neither Dean nor Cas had forgiven each other, and nor had they redeemed themselves in the other’s eyes – but the door had been left open for it. As Dean says in “The Born Again Identity” (or would’ve said, had TPTB not stupidly cut the line from the episode) I never stopped wanting to fix it – which is essentially what Bobby says right here.
Finally, in case you had any last doubts that “Death’s Door” is meant to foreshadow Dean’s eventual confrontation of his grief, I’ll leave you with one last parallel:
Daddy Singer (to young!Bobby): What is the matter with you? You break everything you touch.
Hester (to Dean in “Reading is Fundamental”): The very touch of you corrupts. When Castiel first laid a hand on you in Hell, he was lost.
Ouch. Right in the feels.
11 – Adventures in Babysitting
As this episode is about Dean and Sam processing the loss of their last remaining parent, the emphasis here isn’t so much on Dean or Cas as about the nature of grief in general. There is, however, some very bad advice offered by a man who’s almost like Bobby Singer, but not quite:
Frank: Do what I did when I was 26 and came home to find my wife and two kids gutted on the floor. Decide to be fine till the end of the week. Make yourself smile, because you’re alive and that’s your job. Then do it again the next week.
Dean: So… fake it?
Frank: I call it being professional. Do it right, with a smile, or don’t do it.
This advice is almost what Bobby tells Dean in “How to Win Friends and Influence Monsters”, but not quite, because while Bobby tells Dean that his grief is valid but dangerous, Frank tells Dean that his grief is a controllable quantity. Dean can be the master of his grief.
It sounds like good advice, doesn’t it? But it really isn’t, because you know who else thought he could master his grief? John Winchester.
Hence why that final scene of Dean forcing a “professional” smile is so sad and terrifying – this is what madness really looks like. Still waters run deep, and Dean’s turmoil — now made so much worse with Bobby’s death – still devours him from the inside-out, but now he is actively hiding from it again, covering it up, running away.
Next time, an in-depth look at Episode 12.