I apologize for getting a bit long winded, but there was just so much of Dean I felt needed to be discussed in this episode.
SAM: Dean, could you be a bigger geek about this?
DEAN: I’m sorry, man, but what about a human by day, a, a freak animal killing machine by moonlight don’t you understand? I mean, werewolves are bad ass. We haven’t seen one since we were kids.
It’s a simple hunt, hunt the bad thing and kill it. No shades of grey. This hunt is the kind Dean has been doing all his life. There’s no confusion about what’s evil, like Lenore, or even Molly. This hunt is a simple identify and eliminate. The hardest part is figuring out who the monster is. So they go talk to the girl who found the body of the lawyer.
MADISON: You get a few Scotches in him and he started hitting on anyone in a five mile radius. You know the type.
SAM: Yeah, I do, actually.
The funny thing is that Dean doesn’t seem to identify with what Madison’s saying, even if Sam can definitely see Dean in that role. Dean is back in full womanizer mode, so busy checking out the girl that he doesn’t even see Sam’s irritation.
In Kurt’s apartment, Dean goes in first, follows the noise on the balcony without asking Sam to go with, the first around the corner when they find the body. Dean is always head first into danger, protecting his brother.
It’s only when they get back to Madison’s apartment that Dean begins to realize there’s something different about Sam on this hunt. Of course Dean noticed Madison. It’s what Dean does, noticing women. Sam didn’t really notice her until he saw Dean noticing her. And once Dean realized that Sam was interested, what did he do? He gave him a hard time, of course. It’s what big brothers do.
SAM: All right, you go, I’ll stay
DEAN: Forget that, you go after the creepy ex. I’m gonna hang here with the hot chick.
SAM: Dude, why do you always get to hang out with the girls?
DEAN: ‘Cause I’m older.
But Dean doesn’t always get to hang with the girl. Usually it’s Sam that protects the girl and Dean that goes after the evil, although there have been some instances this season where that has changed, Nightshifter, Roadkill. We see Dean leaving to kill the bad thing while Sam stays with the girl time after time. In Wendigo, Skin, Hookman, Provenance, Salvation, Bloodlust, Nightshifter and Roadkill, Dean lets Sam interact with the damsel in distress. Even in Dead in the Water, Sam was the one saving Andrea while Dean dealt with Lucas. The exceptions were Scarecrow, when Sam wasn’t with Dean, Route 666 with Dean’s ex-girlfriend Cassie, and No Exit with Jo, though with that last one it could be argued that Dean was more interested in protecting Jo than hitting on her.
Dean will do whatever is in his power to do to make sure Sam gets what he needs, even if Sam doesn’t quite know what that is, or won’t admit it. Even if Dean has to push him into realizing what he wants. “I want you to be honest with yourself” he told Sam in CSPWDT. I think that if Dean hadn’t pretended interest in Madison, Sam would never have acted on his attraction to the woman. So Dean gives Sam a hard time and they end up settling things the old fashioned way, by playing rock/paper/scissors. Honestly I think it’s less ‘Dean, always with the scissors’ than ‘Sammy, always with the rock’. Sam wins, of course, not once but twice because Dean lets him win. And still Dean knows Sam well enough to guess what’s going on after he leaves.
DEAN: Let me guess, you’re sittin’ on her couch like a stiff tryin’ to think of somethin’ to say.
He knows his brother. Knows how he operates, knows how awkward getting back in the game has to be for the younger Winchester. And yet he still tries to goad him into having a little fun.
DEAN: What’s she wearin?
SAM: Bye, Dean. (hangs up)
DEAN: Ah, Sammy.
So Dean goes after Kurt, finding the man in a strip club. The stripper scene is classic Dean. Staring up at the woman, watching her more than Kurt, Dean is in his element. He’s got a good hunt, his brother’s in the perfect spot to get laid, and Dean has a half naked woman in front of him. What could be better?
DEAN: I don’t wanna miss anything.
There are some that criticize Dean for his one night stands, but I think he has every reason to limit his relationships. After Mary died, John spent the rest of his life mourning her. Sam spent nearly two years mourning Jessica. Deep down Dean has to have the same fear that if he ever tried to settle down, one night he’d look up at the ceiling and find his love on fire. The one time Dean was tempted to get serious about someone, told her the truth about his life, Cassie flat out rejected him.
Later that night Dean stands outside of Kurt’s apartment, watching, checking his gun, waiting for the bad guy. Dean in his element, the classic hunter in the wild. He knows how this should go and he’s more than ready for it. He’s stunned when he sees that the werewolf is Madison. You can almost see the wheels turning, wondering if she killed Sam before she came to visit Kurt. Even thrown against the wall and on the edge of passing out, the hunter in Dean is still with it enough to pull a silver knife and slash at the werewolf, fending her off as he slips into unconsciousness.
As soon as he wakes up, Dean calls Sam. Though he doesn’t ask if Sam’s all right, I have to believe that part of Dean’s irritation during the conversation is that he was worried about his brother. Upon returning to Madison’s apartment, Dean feels no reason to be nice to Madison. She’s a monster, just another thing to hunt and kill. It takes Sam a lot to convince him to even try to save her.
DEAN: Yeah, she’s killin people!
SAM: But if she has no control over it--
DEAN: Exactly, she can’t control it. Look, even if she’s tellin’ the truth it doesn’t change anything!
SAM: I’m not putting a bullet through some girl’s chest who has no idea what’s happening!
DEAN: Sam, she’s a monster and you’re feelin’ sorry for her?
SAM: Maybe I understand her.
What can Dean say to that reference to what happened in BUaBS? Sam had no control over his actions while he was possessed, and once the demon was exorcised, he didn’t remember everything that had happened. Even though he does remember some of what happened when the Demon had control, Sam can identify with Madison.
SAM: Dean, please. We can save this girl.
This is when Dean starts to realize how invested Sam has become in Madison, in saving her. Sam has said before that he believes every person he saves will help him avert his own dark destiny, and Madison is no exception. Dean has no choice but to agree to try the possible cure found in Dad’s journal. Again, it comes back to Dean being unable to say no to his brother. He reluctantly agrees to go hunt but only after Sam promises that he’ll shoot Madison if she gets loose.
Dean hunts down the other werewolf and shoots it without hesitation. He’s a bit irritated when the girl he saves runs off (from Hunted: “we don’t get paid, we don’t get thanked”) then kneels next to Glenn’s side. He’s a little freaked when he realizes that Glenn doesn’t remember anything that happened, which I believe is another way these werewolves remind him of Sam when he was possessed in BUaBS. In the car, he admits to Sam that he’s sad because Glenn had no clue what was going on. He is prompted to try and understand why Glenn turned Madison instead of killing her, suggesting that deep down Glenn was looking for a mate. He takes the opportunity to point out that this is the best chance Sam will have with Madison.
DEAN: Speaking of Madison...
SAM: Oh, whatever.
DEAN: Don’t whatever me, man. You liked her, maybe ah...
SAM: Dean, she thought I was a stark raving lunatic.
DEAN: You saved her life.
When Madison comes to the car, Dean is the one who is honest with her about why they’re lurking. Sam’s connection with Madison is driven even further home when they return to her apartment and he watches the interaction between Sam and Madison closely. You can see the moment when he realizes that Sam is interested in the girl, and does his best to ease the awkward moment by suggesting poker. Later he’s sitting to one side with his gun while Sam and Madison are talking on the couch, trying to give them space even as he’s watching over his little brother.
When the sun rises and Madison hugs Sam, there is a split second when Dean has this sappy look on his face, like he’s so happy that Sam has found someone he can connect with. He covers it quickly, coughing and finding an excuse to leave the two of them alone. That fist pump and final look back as he walks out? That right there is one of the reasons I love Dean. He’s so freaking happy his little brother is finally gonna get laid...
Sam pounding on the hotel room door freaks Dean out a little. His eyes shift down, taking in the fact that Sam isn’t wearing quite as many layers as he was when Dean left him at Madison’s even as he’s making sure Sam isn’t hurt. Dean immediately does his best to reassure his brother that they’ll find Madison.
Even though Dean tries to understand how Madison could still be a werewolf and not have shifted, he’s keeping a level head, realistic about what has to happen now.
DEAN: Sammy, I don’t think we got a choice here any more.
SAM: What?
DEAN: I hate to say it, she’s a sweet girl, but part of her is--
SAM: Evil?
DEAN: Yeah.
SAM: Yeah, that’s what they say about me, Dean. So me you won’t kill but her you’re just gonna blow away?
Sam has a point, and Dean knows it, even if Sam doesn’t understand his brother’s reasons, it doesn’t change the facts. Madison is a monster, and there is no cure. Dean tells her the truths that Sam can’t bring himself to utter. He won’t let Sam lie to her, laying out rather sympathetically the situation, how there are no good options, there is no cure. In a way he’s talking more to Sam than to Madison, even when he apologizes to her.
Dean watches Madison pick up the gun and the following conversation just about kills me. Not because it obviously just about kills Sam, but because of how close it is to the conversation between Demon!Sam and Dean in BUaBS. Madison’s words have to be just as cutting to Dean as they are to Sam. Compare the two conversations. Quotes in parenthesis are from BUaBS, and not in the order they were spoken in that episode.
MADISON: So I guess that’s all there is to it then.
(SAM: You said it once yourself, Dean. I gotta face up to who I am.)
SAM: Stop. Don’t talk like that.
(DEAN: I didn’t mean this!)
MADISON: Sam, I don’t wanna hurt anyone else, I don’t wanna hurt you. (picks up gun, tries to give it to Sam)
(SAM: (takes a handgun from his duffel, shoves it at DEAN) I don’t want to hurt anyone else. I don’t want to hurt you.)
SAM: Put that down.
(DEAN: Whatever this is, you can fight it.)
MADISON: I can’t do it myself. I need you to help me.
(SAM: No. I can’t. Not forever.)
SAM: Madison, no.
(DEAN: Shut up, Sam.)
MADISON: Sam, I’m a monster.
(SAM: Dean, it feels like no matter what I do, slowly but surely I’m, I’m just becoming...)
SAM: You don’t have to be. We can find a way, alright? I can. I’m gonna save you.
(DEAN: No. Listen to me. We’re going to figure this out. Okay? I mean, there’s got to be a way, right?)
MADISON: (crying) You tried. I know you tried. This is all there is left. Help me, Sam. I want you to do it. I want it to be you.
(SAM: Here, you gotta do it.)
SAM: I can’t.
(DEAN: You know, I’ve tried to hard to keep you safe.)
MADISON: I don’t wanna die, I don’t, but I can’t live like this. This is the way you can save me. Please? I’m asking you to save me.
(SAM: Dean, you promised him. You promised me.)
Sam shakes his head no, and Dean steps up, as Dean always will, to do the hard part, to spare his brother. They all know that there is no other choice here. Dean takes the gun from Madison, wordlessly telling Sam that he’ll take care of it for him.
The choice of song here is particularly poignant. It’s all a bad dream the song says. Face your fears. I will be watching over you… gonna help you through. The song is from the point of view of someone trying to reassure a child, Dean’s point of view as he tries to take on this awful responsibility for his brother, struggles to help him. I will protect you in the night.
When Sam walks away, Dean follows him into the kitchen. He doesn’t try to comfort Madison, his only thought is for his brother. He can do it, he can kill Madison, but he wants to make sure that Sam is alright with it, he needs Sam’s permission.
DEAN: Sam. I’m sorry.
I’m sorry I couldn’t protect you from this. I’m sorry we couldn’t save her.
SAM: No, you’re right, she’s right.
DEAN: Sammy, I got this one, I’ll do it.
I couldn’t protect you from caring for her, but I can protect you from this.
SAM: She asked me to.
DEAN: You don’t have to.
I’ll do anything for you. Let me take this burden.
SAM: Yes, I do. Please.
He doesn’t want to give Sam the gun, he’d rather protect him, but he hands it over because he knows Sam needs to do this.
SAM: Just wait here.
In Skin, Dean tells Sam “I really wish things could be different, you know? I wish you could just be... Joe College.” Despite the life the boys have lived, Dean has done his best to preserve as much of Sam’s innocence as possible. It shows in the way Dean does most of the killing, how he constantly puts himself between Sam and danger. But this is something he can’t protect Sam from, something Sam won’t let Dean protect him from.
Dean watches his brother walk away, watches Sam turn for one last look, one deep breath to gather himself. Dean has always been like a father to Sam, and now he has to watch his son grow up, watch him face things Dean would just as soon Sam never have to face.
Above and beyond that though is the knowledge that Madison cannot be saved, and that despite Dean’s promises and intentions, there may come a day when Sam cannot be saved, that the only way it will end is with Dean putting a bullet in his brother’s head or heart.
And so Dean waits, facing forward rather than turning to watch Sam become a man. A tear forms, runs down his cheek. He jumps when the gunshot echoes. Dean’s heart breaks for Sammy, for the choices made there in Madison’s apartment and the choices Dean may have to make in the future, and ours break right along with it.
spn_heavymeta 
lostandalone22 - (no subject) [+1]
Thank you again! Very nicely done.
Cheers ~
Erin
I agree. To Dean, Jo was like another sibling, someone he had to watch out for - in part because she basically had him lie to Ellen on her behalf. And Dean felt a responsibility to Ellen to see her daughter home safely.
Deep down Dean has to have the same fear that if he ever tried to settle down, one night he’d look up at the ceiling and find his love on fire. The one time Dean was tempted to get serious about someone, told her the truth about his life, Cassie flat out rejected him.
I completely agree. I mean, I'm sure that their childhood/teenager lifestyle didn't really predispose them to forming lasting relationships or falling in love (moving around all the time, etc.), but until Cassie, Dean probably wasn't in one place long enough to really have a serious relationship. And a fear that what happened to Jess and Mary will some day happen to whatever girl he cares about is very true and real and rational.
This is so on. Thanks so much for sharing.