The premise of “About A Boy” fits this risk taking mold. In it, we have the concept that a witch spell has the power to de-age one of the Winchesters---in this case, Dean. On the surface, it's a concept that seems like it might not work. After all, for a good portion of the episode, one half of the two lead actors would be missing, replaced by another actor playing one of the Winchesters. It's a gamble to do something like this---especially when that other actor isn't merely playing Dean in flashback.
And yet, this risk taking works. Not only does it work, it also gives us deeper insight into the episode's underlying message: that we should take chances.
So many fans cite this show as inspiring them to do something they wouldn't have done before. Some have taken up new hobbies. Others have made career changes. Some have made trips to places they wouldn't have dreamed of every going to---all because the show inspired them in some way to take a chance and see where it leads them. It's a theme that connects well with the audience in “About A Boy,” because without risk there can be no reward. Without taking a chance, we will never be able to make a change or overcome an obstacle.
And that's exactly what both Winchesters need to do in this episode---and going forward---if they're going to beat the obstacle that is the Mark of Cain.
Let's begin with Dean.
We first see him in his room at the Bunker, poring over lore books. He's looking for anything that may lead to some breakthrough. Even though Dean has already looked at each and everyone of these texts already, he is determined that this time he shall find something new, something he or Sam may have missed that will help him to remove the Mark and cleanse him from its dark influence.
And yet, as we see him move about his room, never leaving it, we can sense that Dean has become stagnant. He's locked himself in this room as punishment for what he did to Charlie---and for what he fears he might do to others. This is a typical Dean response to something like this. Unable to trust himself out in the world where he may not be able to control the Mark, Dean has decided to put himself in lock down, keeping himself away from everyone. Dean knows that it is only a matter of time before he could hurt someone else, and so by removing himself from the world he hopes to prevent it from happening---even if he knows deep down that this will not work, either.
Sam interrupts his brooding and futile research attempts to tell him about a new case---one where people are going missing---all but their clothes. It's not much to go on, but the Winchesters have gone to investigate for much less in the past. It's something to get them out of the Bunker and back on the road.
Instead of jumping at the chance, Dean offers Sam's tablet back to him, remarking, “Why don't you check it out? I'll hold down the fort.”
Dean doesn't even trust himself to go on this case. This causes Sam to explode in frustration. He shouts at his brother, “Staying locked up in here, sitting on the ground reading the same lore books over and over and over again---it's not helping you. You need to get back in the game for your own good. You can beat this, Dean.”
As Dean deflects Sam's angry outburst by pointing out, “You believed in the Easter Bunny until you were 12,” we can sense that he's hoping he'll manage to get out of going along. Unable to out-stubborn his brother, however, Dean has to give in and they make their way to the case to learn what might be happening to these missing people.
Dressed in their Fed suits, their first witness seems less than ideal. It's clear by Dean's frustrated, “Don't say it,” to the man's insistence on aliens that Dean's already regretting this chance taking. He doesn't want to be on this case, and he most certainly does not want to be talking to some crack pot about alien abduction. But, they did drive all this way, and so onto the next witness pool---at the local dive bar.
It is here that we see Dean take his second chance. Sam suggests that they split up. He can go and check in on the missing man's apartment and learn what there is to know there while Dean talks to the bar patrons. Dean hesitates, looking nervous and uptight about the proposition about being left to do this without Sam's steadying presence nearby. After what happened last case with Charlie, it's obvious that Dean is worried he may have a repeat experience with someone else.
Sam backtracks quickly, telling him that he's willing to go with him to the bar if that's what Dean wants, but Dean waves him off, quipping, “Hey look, it's a dive bar. It's my comfort zone.”
Inside the bar, Dean makes his way to the counter and prepares to question the bartender. There, he's faced with bottles of alcohol, something he's chosen to abstain from until the Mark has been removed. Prompted by what his brother said back at the Bunker, however, Dean decides to order “something dark and strong” on hand and “believe” in himself. It's the third chance he takes in this episode---and as he drinks this first shot, he hears the distinctive hum of the Mark in his ears, trying to overpower him. And yet, as he's addressed by the woman, Tina, at the bar, Dean manages to squash its hum to talk to her.
It's another risk, engaging not only in business discussions with the woman, but sharing more drinks and childhood stories. Dean needed to learn about JP, and Tina knew something about him. She knew that she wouldn't buy a car from him for instance. The little she knows, however, doesn't quite seem to push the case any more forward. By the end of their time at the bar, they've shared their stories about staying at the same motel---and not much else related to the case at hand.
Dean's risk taking, so far, has paid off. He didn't lose it after drinking more than the one drink, and he didn't do anything to Tina. It's a good sign that what Sam's been telling him all along is right. Maybe he can do this.
Dean's next risk, however, is one that he didn't see coming. Convinced that something is off about the man following Tina out the door, he goes after them to investigate, only to hear her scream and a bright white flash. Before he can look even further, Dean is himself facing the same bright light---and when he comes to he looks at himself in the mirror only to realize that he's been transformed into a fourteen year old version of himself.
It opens up possibilities for Dean. In this younger body, he's missing the constant hum and drive from the Mark. It's no longer on his arm---and it's no longer pushing him to kill anyone and everyone. This, as far as Dean's concerned, may be a second chance. His risk taking by going on this case may have an upside---even if it is an unusual one. After all, they wanted the Mark gone, now it's gone.
But that leaves him with another risky situation. He's now in the basement of some house where JP, the man they had come to find, is taken by the man that he saw at the bar. Either he gets out of here now, or he may end up being dragged upstairs next. Dean may physically be fourteen, but he's still mentally thirty six, and so he automatically goes about finding an escape route that will get him back to Sam so they can both come back for Tina.
Once Dean manages that and gets back to his brother, we see the other reasons Dean needs to take all these risks. He had to do this in order to move forward---as Charlie put it when asked about her mood after being split. It may also perhaps clear his mind so he can find a new tactic in helping control the Mark, but those aren't the only reasons. Dean needed this experience to realize why he's doing this, why he hunts---and most importantly why he hunts with his brother at his side.
As Dean explains to a flabbergasted and freaked out Sam what happened, we see the brothers ease back into a simple relationship---a comfortable relationship. They may be facing a wacky and unimaginable situation with Dean's current physical state, but at the same time, there's a nice ease with how they work this case together. They banter playfully---Dean quips about Sam's size---and inability to fit in the window---, “First time you ever had to say that, huh?” and Sam's retort, “Big talk from the guy wearing Underoos.” They walk in tandem towards the house. They fight over the seat adjustment briefly as Dean shoves Sam's knees to his face. These little moments are sometimes what makes their relationship more than partnership. It's what makes them brothers.
This is just the two of them working together as a single unit on a single goal without anything coming in the middle. There's no Mark to needle him. He's not constantly feeling its tug to do something brutal to anyone near him. Considering the person near him the most often is his brother, we can sense that Dean's relishing the ability to simply be with his brother without the Mark prodding at him to finish what Demon Dean started. Instead, he's simply able to work with his brother. In other words, the risky chance he took in going on this case has paid off in dividends for him.
And yet, it's never that simple for a Winchester. After all, the Mark may be gone, but he's now vulnerable. To even contemplate staying this way---as he tells Sam, “Maybe we don't. If it's between being a psycho rage monster slash borderline demon or a teenager, well” and “Hey look, I'm not a fan either, but Sam, this is problem solved,”--- is a risk in itself. He may have survived being a fourteen year old hunter once before, but that was a different time. Dean's managed to make a lot more dangerous enemies that would certainly take advantage of his new size. Even with his knowledge and skill set, Dean will have a hard time doing what he does without the body mass to back it up.
As he learns when they go in to save Tina from Hansel and the witch, Katja.
Searching the basement, Dean is attacked by Hansel---and easily overpowered. It's the first time his new size has come back to haunt him---and it won't be the last. If not for Sam's intervention, there's no way he would have survived.
The brothers are then mislead by Hansel as he convinces them that he'll help them kill Katja. He leads them to her gruesome kitchen, where they're disarmed and forced to their knees. It's another sticky situation for the Winchesters. Dean, true to form, never stops running his mouth to quip. He remarks that children, “taste like chicken,” and “I blame Obama” for all the Amber Alerts. It's a risk to keep running his mouth---but if he doesn't, Sam might not be able to pull a weapon and launch an attack.
Once again, his new size comes back to bite him. He is easily overpowered by Hansel, beaten and pummeled into the floor and a corner, unable to land hard enough blows to really make a difference. He may know where to strike and how, but he just can't make them have impact---not now. And so, Dean takes his greatest risk in the episode. He snatches the hex bag that turned him in the first place---knowing that it is the one thing that can turn him back after Hansel told them both it could. If he has any chance of fighting back, if he has any hope of being able to save Tina or to stop this spell from hitting his brother---or Hansel outright killing Sam---he'll have to do the last thing he wanted to do: change back.
He knows what this will do. He knows that the moment he's an adult again that the Mark will return and it will slam into him full force. It's been a few hours without its constant bombardment, and he fears that if he should turn back now that he'll be unable to stop himself from not only killing Hansel and Katja, he'll kill Tina and Sam, too. He knows this risk and yet he knows he has to take this great chance in order to get them out of here alive.
And so he does, and he manages to kill only those he intends---even if it does cost Tina the hex bag she needed to be returned to her true age.
As they talk to her about reversing the spell, she declines, telling them, “I've got three ex husbands, $50,000 in debt, and not much else. This is my second chance.”
Chance. It's what this episode has been all about for Dean, and he'll certainly have to take more risks in the future if he's to have any hope of beating the Mark in the end.
But what of Sam?
When we begin, Sam has come into Dean's room with a case, hopeful that he can perhaps drag his brother away from the Bunker. He doesn't want to see his brother caged in this room, chained to these lore books that haven't yielded anything new overnight. Sam has taken Charlie's words to heart---and he's desperate that his brother do the same. He wants Dean to move forward. Instead, he's watching his brother stagnate in his room, unable to go outside. Sam knows that they can't help anyone---most of all Dean---if they stay here cooped up.
This is Sam's first chance. He knows he's risking his brother repeating the massacre at Randy's or the beating of Charlie. He knows that Dean could collapse under the burden of the Mark if they go out into the world and take on cases. It's one reason Sam was so hesitant to take on cases after he cured Dean in the first place. Sam didn't want his brother to be placed in a risky situation that would set his brother up to succumb to the Mark. He wanted them holed up in hotels or the Bunker or anywhere else that kept them from having to face such danger.
And yet he knows now that it won't work. Dean had told him that he wanted to work, that hunting was his “normal.” Right now, the man sitting on the floor of his bedroom staring at the same text isn't his brother. And it's not normal for Dean to be cooped up like this. Sam knows it. His gentle push to look at the case he's found turns frustrated and irate. It's the only way he knows how to get his brother angry---or at least sparked enough to get up and do something about it. So, he tells him, “Charlie forgave you! Why don't you try forgiving yourself!”
This doesn't work---but the mild teasing banter about his belief in the Easter Bunny does---breaking the heavy tension of the room and their conversation about Dean's sudden agoraphobia. Sam has managed to out-stubborn his brother, and now they'll have to go through with investigating the case. It's a risk---one that Sam's willing to take. He told Dean that they can “beat this” and he meant it. It's not a simple pep talk or to appease his brother---but he knows that they must take this first step if they have any hope in actually getting to that point.
The second chance Sam takes is when he accepts Dean's decision to go to the bar and question the witnesses alone. Sam, having experienced the mistrust Dean is aiming at himself---especially after his demon blood addiction---knows how important it is to show Dean that he's backing his words with actions. He offers gently to stay, that they don't have to split up, but backs down as soon as Dean says he's okay. It's a crucial moment if they're to remain the unit they've truly become since Dean's cure. Sam must take a risk like this---and perhaps more than once---if he is to get his brother to see that they can truly beat this. It may also be the only way to convince Dean that he can trust himself---if Sam trusts him this much, maybe Dean will follow his example.
Sam's third chance comes after he realizes his brother isn't at the bar, waiting for him. He pulls his phone out, and calls his brother---only to hear it ring from the bar's counter. The bartender is holding his brother's jacket and phone. Sam demands to know where the bartender got Dean's jacket from---and instead of getting answers, he's blown off. Considering that this man has his brother's jacket and phone, Sam jumps to the conclusion that perhaps this might be their guy---or at least might know where next to look for his now missing brother. Instead of taking a deep breath and asking again, he slams the bartender into the counter.
This is a risk on Sam's part. He didn't follow the man into a secluded area. He didn't make any attempt to hide what he was doing. He did this in front of all the other bar patrons. Any one of them could have jumped to the bartender's defense. And if this bartender had been the one they were after---the monster responsible for the disappearances---he could have easily had a real fight on his hands. It could have ended badly, too, if Sam didn't have the right weapon on hand to handle him, either.
Luckily, this chance pays off for Sam. He's told what he needs to know---the jacket was behind a dumpster. As he goes to search, Sam finds his brother's boots and gun---and a clue. The “flowery flowers” the first witness mentioned coat Dean's gun, and now Sam can start to figure out what it is and how it's connected to their case and Dean's disappearance.
The fourth chance Sam takes is helping his de-aged brother go to rescue Tina. Sam doesn't question for a moment Dean's skill or his reasoning. He knows that they're here to do just this. It's why they went on this case in the first place. It'd be silly to not follow through despite what has happened to Dean. And yet, as we watch the brothers fall into that easy relationship of banter---where the Mark isn't lingering between them like an angry miasma taunting them at every turn---we can tell that Sam is disturbed by what has happened to his brother.
Sam is thrilled by the fact that the Mark is gone---but he knows that this isn't the answer they're looking for, either. He knows this, too, from experience. After all, the Wall Death put in his mind was easily broken. He sees this de-age spell exactly for it is: a quick fix and a dangerous one at that. It's too easy to simply get rid of the Mark this way and wait for Dean to “grow up” again. He knows that at some point the spell would have more adverse effects---either doing something more to Dean than it already has or leaving him vulnerable to anyone they've faced in the last ten years especially.
Sam, too, can see that this would lead to other complications. He just managed to get his brother out of the Bunker, after all. If Dean were to stay this age, they may have to stay there just to keep him from being attacked by someone his current physical size couldn't contend with---another poor combination for them.
But most of all, it exposes another undercurrent about what Sam really wants, something he won't express directly until the case is finally concluded.
So, Sam goes with Dean to save Tina, trying to enjoy the way he and his brother are working together---without the Mark's influence hanging directly between them.
His fifth chance comes when they confront Hansel. With Dean standing right next to him, Sam demands to know how to turn his brother back. On the surface, this seems reasonable. After all, they're here to save Tina and they'll need to know how to do that for her. But underneath---and considering their earlier conversation---Sam is treading on dangerous ground. Dean's already expressed a desire that he may want to stay this way---even if it's inconvenient or awkward. They've had such a comfortable relationship lately---especially on this case---and Sam's risking a potential fight after it's done for doing this. Sam's forceful in demanding this answer, his voice breaking with heavy emotion. He won't let them finish what they started until Hansel tells them how to undo the spell.
It's simple, squeeze the hex bag again, and become your true age. It's the information Sam needed, and now they can finally move on to taking down Katja.
Sam's worries about Dean's size come to pass as they're both overpowered by Hansel and Katja. She tosses him hard against a cabinet, her powerful spell seemingly to stun him both physically and mentally as he crumples into a fazed heap, trying to regain his composure. Sam knew this case was a risk. He took a chance on it, knowing that his brother would be facing the difficulty of contending with the Mark while facing a life and death station at some point during it. Sam knows that what they do is dangerous. It's part of the hunter territory---and now he's worried that he's perhaps unable to stop what Hansel will do to Dean in his new vulnerable state.
That is, until, he sees Dean grasp the necessary hex bag to turn back.
Sam watches as his brother---the one that he is so used to having at his side---returns to his full adult size and brutally and efficiently handle both Hansel and Katja. There's the cold and calculated look on his brother's face as he stabs Hansel to death, and as he stalks Katja, the look on his face turns murderous and cruel. The hex bag, the very same one that Dean may have used to become a teen again after they kill these two, is promptly stuffed into the witch's mouth, and she's shoved brutally into the furnace to burn to death. Dean doesn't say a single word while making these kills. He just does it.
And then, Sam's risk taking pays off in dividends.
Instead of killing him and Tina to satiate the newly returned Mark, Dean seems able to hold it together and finish their case. He helps free Tina, and they lead her outside to deliver her the bad news about the hex bag. She'll have to remain a teenaged version of herself while Dean was lucky enough to change back.
Once they drop her off at the bus station, the brothers discuss the case---and the new information they garnered about Rowena and the Grand Coven. Sam can see straight through Dean's attempt to paint the witch coven as an 80's hair band. He knows his brother doesn't want to talk about what happened---or more importantly what didn't happen. And he wants to see for himself if the Mark is once again back on his brother---even if he knows that it will be.
Dean pulls up his sleeve, revealing the ugly blemish back on his skin, an angry red and puffy as if its telling them both that it was most displeased to be gone from its host for even a few hours.
Despite going through this wacky case---and Dean experiencing the awkwardness of puberty yet again---they're back where they started all over again. Dean still has the Mark and they still have to find a way to control or remove it.
Sam can sense that is brother is already regretting returning to himself before Dean can even say it. He wants to reaffirm what he said before they took this case. Sam wants to break through Dean's stubborn streak---with his own. His brother needs to hear this almost as much as Sam needs to say it. And so, he says, “Look, man do I wish the Mark was gone? Yes of course, absolutely I do. But I wanted you back, and here you are and you didn't Hulk out, I'll take the win.”
It is perhaps the statement of Sam's story this season. It's one he's made to others throughout---to Demon Dean, to Crowley, and to Castiel---and now he's told his brother directly. He wanted Dean back---and it's what he's wanted all this season.
And yet, Sam knows that if they're going to get his brother back whole---free of the Mark---they're going to have to take chances.
In the end, when they “beat this,” all those risks will be more than worth it---and for Sam, that's all that matters.