SAM, if I were your brother, I'd have hit you in this episode. Or at the very least put hair-dye in your shampoo!
Ok, so I finally finished re-watching Don't Go Into the Woods, and I noticed that Sam is doing the same thing he did with Claire Novak a little bit!
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So, at the start of the episode, he doesn't even seem all that aware of the stress Jack, Dean, Cas are under. In the previous episode, Peace of Mind, Sam is wrapped up in his own grief and failings, and Cas steps in to mentor him (note Cas also wanted to let Dean get some much-needed sleep).
Here, in Don't Go Into the Woods, Sam starts out gung-ho about the hunt, but by the end of the episode, he's clamped onto his moral-fixation-of-the-moment, inspired by the case-of-the-week, where a Dean-and-Cas coded sheriff has lied to a son to protect him.
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And here's the thing. It's a little bit true, right? Dean is tiptoeing around Jack, lying to him, chipperly telling him that "his mission is SHOPPING!"
BUT.
Sam's being sanctimonious-Sam here.
Because... Dean's been the one trying to take care of Sam AND Jack when Sam was running everyone ragged by diving into case after case (when Sam was trying to forget about losing the AU hunters).
Now, weeks later, Sam suddenly checks back in to trying to be apart of the co-parenting village.
DEAN: So telling the kid—you think that's the best idea? SAM: What? You don't? DEAN: It doesn't make his life any better, you know?
Oof. Ow.
Dean is so sad.
He knows something is wrong with his kid, but he doesn't know how to fix it. BECAUSE it's not simple. On top of Dean being afraid, he knows Jack’s powers are a historical sore spot and that bringing it up might hurt Jack. (NOTE: Dean’s instinct is usually truth-telling with Jack, but this feels different… bigger.)
But Sam? After weeks of being "out of it," Sam has now hyper-focused on The Good (simple) Thing (TM) he thinks is gonna fix it.
For Sam, it's simply this: Don't lie, and everything else solves itself! :D Talk it out, and all your problems will just melt away.
DEAN: I took care of it, okay? We took care of it. SAM: No, no Dean. We did not take care of it.
(BRB, hitting Sam with a newspaper. )
Sam is framing this as a "Dean is so controlling" issue. In fact, it's a part of a larger "Sam has been checking out," context.
And hey—we are absolutely sympathetic to Sam checking out, to using hunting to ease his turbulence. He's not the only character to do so!
However, Sam is a character that tends to check out, come back, and immediately go into sanctimonious LECTURE mode and that’s what’s frustrating:
SAM (judgily): No, no Dean. We did not take care of it. You did.
(Yeah, Sam. That's kind of the whole friggin' point here!!!)
For weeks now, Dean and Cas having been trying their darnedest to take care of YOU, of Jack, of everything! Dean is even the one who checked in on the phone with your friend ROWENA.
Cas is going the other direction, taking on too much. He's out trying to take care of things ON HIS OWN AS YOU SPEAK. Dean's on the hold-down-the-fort-homefront, and Cas is on the big-solution-oriented-battlefront.
All Dean does is exhale a little. "Ha..."
SAM: And do you think you really took care of it the right way?
....
......................................
Sam. Sammy.
....
Anyway, poor Dean. He's hit with this... blunt, hamfisted unkindness from Sam, even after Dean’s Michael-possession and superhuman efforts to take care of everyone. So, he defensively scrambles:
DEAN: "Jack said he was fine."
And obviously, Dean knows Jack isn't fine.
Dean’s the one that was wanting to give Jack more space and time before going hunting, after all. (See: beginning of this VERY episode. Where Sam wasn't even thinking about Jack's wellbeing at all.)
It hasn't, in fact, been on Sam’s radar for weeks at this point. Sam wanted to take Jack on a hunt to make himself feel better!!! Sam was the one who started this episode berating Dean for not wanting to bring Jack along and sassily reminding him that Jack was (via Donatello) "is in the clear."
In short, even when Sam is talking about truth, he isn’t keyed into Jack’s wellbeing forJack’s wellbeing’s sake. He’s in solve-it mode, and he identifies lying as Theeee Issue:
SAM: "He's a kid. And when we were kids, how many times did we tell dad we say were fine just to make him happy?"
...
Oh.
Like you did earlier this very episode, Sam?
*coughs*
Sigh.
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In the context of the last few weeks and his utter cluelessness in the beginning of this episode, wanna know why I think Sam is using this issue as a crutch?
Because now that Sam's checked into the village parenting club again, he's latching onto something that's easier to control than everything else: words. ✅
Sam's simplifying the whole situation…
(It's why Sam's boundaries with Jack tend to be "easy-mode" parenting, like his berating Jack's sugary sweets/diet. These are tasks that allow Sam to remain "the good guy in Jack's corner" without doing the "hard-mode" parenting that turns the parent into a Bad Guy.)
Sam thinks talking out "the truth" will magically fix Jack's complex power-and-soul issues... ones Sam's been conveniently ignoring for weeks.
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And Dean is being so beautifully understanding about it. Acquiescing and trying things Sam's way…
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When they get back, Sam slinks in the background at first, letting Dean do the greeting and the talking, waiting for his moment to swoop in and provide "sage, Sammy-time advice" That he has no doubt been rehearsing silently in the car.
And Dean... despite shielding Jack from the truth this time, is being honest in other small emotional ways. He emphasizes how he didn't particularly like the gross parts of the hunt. Camaraderie.
[[Aside/// funny how in the very beginning of the episode, Sam judgmentally raked Dean over the FUCKIN' COALS for jumping at the sight of the gross/dead body. "How many years you been doing this job, Dean? Etc etc. Funny little bookend.]]
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ANYWAY.
Enter Sam. Aaaaaand: Parent mode activated!
God help us.
DEAN, comically “annoyed” that Jack didn't get the beer...
....and MAYBE wondering if Sam's bull-in-the-China-shop parenting is actually going to work. Spoiler: it doesn’t!
The thing is, Sam is right about some aspects of this! It's a good thing to talk to Jack about his powers! Like how Cas needs to talk to Jack about the snake! How Dean needs to stop being so afraid of the truth that he goes into denial mode!
BUT!!!!!
The Sam methods tend to chafe.
Jack's been INCREDIBLY defensive lately, something Cas and Dean clocked well and have clearly talked about with each other. (SEE: In Peace of Mind, they both used the snake to talk to Jack soas not to trigger Jack's defensiveness.)
But Sam? Sam's been waaaaay outta the loop. And it shows.
SAM: Jack LISTEN. Dean and I wanted to talk to you about your powers.
And again, I'm not saying Sam's wrong. He's just... unfortunately very Sam about things even when he's right. (NOTE: He's able to occasionally give supportive advice, like to Mary about AU Bobby!)
Also, there's no real... 100% wrong stance here because the whole soul situation sucks. After all, maybe it would've been better for Jack to come along with them, or maybe it would've gone terribly wrong.
(Aside// And while Dean may have good intentions to lie to protect his son and protect him from pain, Dean definitely doesn't want his partner Cas to lie to him to spare him pain. Around and around we go!)
(Aside aside/// Or, actually, via the script, that's not quite true. He SIMULTANEOUSLY wants Cas to tell him about the snake, and he DOESN'T want Cas to tell him about the snake. Lol, oh the spouse-codedness of that. Similar to the lon-running pattern of Dean wanting to protect and be protected by Cas. SEE: “So you’re faster. / Wait, you’re gonna take on that many angels?”)
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ANYHOO. Dean gracefully enters the conversation, supporting Sam while trying to be frank but IMHO clearly having misgivings about this approach and timing:
DEAN: It was crappy of us not to tell you. You know, we were trying to be nice. 'Cause we care about you. But because we care about you, you deserve the truth.
And Jack has a moment of indecision here, clearly thinking about his own lie. Even with his past shame related to powers/control, Jack might’ve ordinarily come clean about his mistake…
But not now. Not with how things have been lately. This is out of character for him, another sign that’s he’s feeling off.
Psychologically wounded from consuming Michael's grace, feeling flat inside, feeling guilty and disconnected from everything... Jack remains quiet.
Not to mention, Sam's up in his face like this:
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Jeebus. No wonder Jack didn't say anything.
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And make no mistake, Jack is annoyed by the constant hovering. He says as much in Game Night, and something about this cerebral-scripted-Sam-method IMHO works the least with Jack.
(We see glimmers of that in Tombstone, too.)
I think Dean actually realizes that Jack's withdrawing here, that this method, despite it's moral clarity, wasn't entirely effective or successful for getting through to Jack:
At least with Cas, Jack allowed himself to get mad, to speak freely. (Same with Mary in Game Night. He lets his real emotions show.)
But this? Sam's pushing?
Jack shuts down:
Dean tips his head back, like "Oh crap." Perhaps thinking to himself, HOLY MOLEY THAT DID NOT WORK AT ALL.
He even makes a Cas face about it: =_=
And the fun part is: Jack knows that Dean knows.
You can see it in the flash of side-eyes he gives Dean here before turning back to Sam. But when Jack looks back to Sam, he does this little "I'm so innocent" act with the hands.
(He also knows from Peace of Mind that Dean isn’t in “pushy mode.”)
And Sam? Sam looks overjoyed and self-satisfied because he's a dumbass who missed... everything.
Dean on the other hand... is... more understanding of the fact that fuck-all progress that actually made here.
He swings his arms like, “Whelp, that was useless.”
Sam is like YISSS I HAVE DONE IT I HAVE CONQUERED PARENTING IN ALL MY WISDOM
DEAN (sarcastically): Great. And I guess I'll go get some beer.