Before we even get started, I think I better lay a few things down. When I say Sam and Dean are soul mates, I’m not talking about the Wincest view of things. I mean that there is no one on the planet who understands Dean more than Sam, and no one who understands Sam more than Dean. They are opposite sides of the same coin. That said, I think it would be tremendously hard to be in love with either of the boys. The girl they chose will always know that they’re number two on the list of allegiances. For Dean, Sam will always come first, and Sam is beginning to become the same way about Dean. That’s my view of it anyway, and I wanted to just clear that up before we even started. So let’s begin.
Route 666 is all about our discovery that Dean had once badly loved and lost. For Dean, this was the most significant romantic relationship he has ever had. Cassie was the one woman he trusted enough to talk to about his work, and for his honesty she broke his heart. This really helps develop Dean's whole “distrust of outsiders” belief, and explains why he is always trying to protect Sam from the inevitable hurt that comes with getting close to anyone. Dean never allowed himself to get close to anyone and the one time he let his guard down he got hurt. If he can save Sam that pain, he’ll try.
When Cassie calls, Dean sees this as his one chance to fix what he did wrong the first time. I think Dean has a more romantic idea of what his relationship with Cassie had been. Although Cassie cared for Dean, I don’t believe she was necessarily as in love with him as he was with her. Dean was just a guy she dated for a while, but he was too emotionally closed off for the relationship to go anywhere. So while Dean is thinking “I can fix this. I can make her stay this time.” Cassie is thinking, “I’m asking for his help because I need it. I’ve moved on, I’m going on with my life without him.” I’ll talk a little about why Dean may have chose Cassie in a minute, but first let’s look at Sam and Dean’s relationship in this episode.
Sam starts off the episode annoying and teasing and so very little brotherish. He wants to understand why this girl was so special that they would drop everything to help her. He pokes and he prods, he jokes and he guesses, and in the end he’s able to break down enough of Dean’s walls to figure out the truth. (And as a complete side note, I absolutely LOVE how much of Sam’s dialogue is him reacting to Dean’s facial expressions. Dean doesn’t confirm anything with words; Sam deducts most of it all by himself, just because he knows Dean that well).
I love how completely open Sam is, and how hard he pushes to get Dean to talk about his feelings. Dean can try to resist but Sam wins in the end because he knows which buttons to push and he knows how to read his brother. Once Sam finally gets the whole story and can see that Dean had once (in a very vague way) considered a normal life, his teasing lessens. He wants to understand Dean and he wants to think they could share this. But “normal” isn’t what Dean wants - not Sam and Cassie’s normal, not 9 to 5, not ‘honey I’m home‘. In the end of the episode, when Sam asks if it is worth putting their lives on hold to do what they do, Dean’s choice couldn’t be clearer. For Dean, Cassie was the diversion from “normal”. Life on the road with his brother, with evil to hunt and people to save - that is his “normal”.
I always found it funny that the TV Guide listed the description to this episode as something like, “Sam and Dean travel to Missouri to investigate a mysterious truck and Sam is stunned to see a new side of his brother as Dean struggles to come to grips with his ex-girlfriend.” I thought it was interesting that Sam was stunned about learning something new about Dean, but is he really? If what Sam was so shocked to find out was that Dean had attempted to sustain a long term relationship, I’d just have him consider the time frame in which Dean and his sudden grasp at normalcy came.
When Sam left for college he put a Sam-sized hole in Dean’s life. For Dean, he’d lost not only his brother, but also his best friend. And although the time line is pretty vague, but I would wager that Dean met Cassie not long after Sam left for college. Dean was feeling vulnerable, he was lonely, and then he meets this girl. A girl who, coincidentally, is a lot like Sam. On one hand we have Sam – who is driven, studious, and stubborn. On the other hand we have Cassie – who is…driven, studious, and stubborn.
If we step back to the Pilot for a moment, we’ll see that this has a neat echo of Jess and Dean. On the surface Jessica doesn’t seem like the type of girl Sam would go for. Sam seems like the type of kid that would rather stay home with a good book then go out and party. But in the Pilot we see Jess dress up and drag him out. So why, out of all the girls on campus, did he choose Jessica who on the surface seems like a poor match? I think that although Sam chose to leave the family business and pursue a normal life, he still missed his brother like crazy. So if he couldn’t be with Dean, he did the next best thing, and attached himself to someone who was also loud, outgoing and fun. Sam had a Dean-sized hole in his life, and he also filled it with a female version of his brother.
What floors me is how they are always drawn to one other, even in their romantic pursuits. That Jess and Dean were identical forces, and that Cassie and Sam were also, shows how deep and all-encompassing Sam and Dean’s bond is. Dean wants to be with Sam and Sam wants to be with Dean, and that’s just the way it is for them.
But back to Cassie and Dean.
I think we have to take into account what episodes directly preceded this, Scarecrow and Faith. There was a lot of emotional upheaval in Dean’s life over the past two episodes. First he gets into a gigantic fight with his brother, his brother leaves him, he gets kidnapped by some tree-god worshipping villagers, and his brother comes back and tells him that they should stick together. Then he has an accident and is given a month to live, is cured by questionable means, and then has to wrestle with the theological question of whether or not his life is worth more than another’s.
Dean’s been on a rollercoaster of emotions lately, and then to top it off, his old girlfriend, his only serious ex-girlfriend, calls him up and wants his help. Dean runs to help her because that’s what Dean does. It doesn’t matter how badly Cassie hurt him; if she’s in trouble, if anyone is in trouble, he’s going to drop what he’s doing and help. I don’t honestly think that Dean went to Missouri believing he would start dating Cassie again. Dean, in this moment, finally has the life he has always wanted – he has Sam, he has his Impala, and he has his work. Cassie represents a different life, the path that was not chosen.
Dean made his choice when he told Cassie about his work. Dean couldn’t choose Cassie and her life without telling her about the family business because his work is so much a part of who he is. I don’t believe Dean could have turned his back on his work and settled down to live the life of normalcy. So instead, he tried to merge his worlds together. He had “normal” with Cassie, but he still needed his work. So he told Cassie the truth.
Where Sam was afraid he would loose Jess if he told her about the family business, Dean realized that he would never be happy unless he was able to bring both of his worlds together. Dean was being true to himself and doing what was it would take to make him happy. The fact that Cassie rejected him only illustrates that she simply wasn’t the girl for him. And to be honest, I don’t know if such a girl exists. Dean will never settle down – not while there is evil to hunt and people in danger. His one night stands and threesomes are about letting off steam and finding enjoyment. He doesn’t need to find a soul mate or a partner. He already has one.
Sam is the most important thing in Dean’s life, but I don‘t know if Sam always knows that. You would think the introduction of Cassie as someone Dean has loved and never mentioned could make Sam reconsider his place in Dean‘s life. Cassie should have made Sam jealous, in the normal, “no one is good enough for my brother” way. But he isn’t. And I wonder why that is.
Maybe Sam gets that Cassie isn’t “the one“, and he is secure enough in his place in Dean’s life to know he’s not going anywhere. Notice Sam doesn’t give Dean the offer of staying when they leave town. For as much as Sam talks about how Dean could have a normal life, he doesn’t seem too eager to really push him into it.
This episode did a lot of things in regards to Dean’s character development. It gave us background on why Dean was so wary of letting strangers into their lives, it showed that he had once tried to be the “normal” that Sam left him to pursue, and it confirmed that to Dean, life on the road is where he belongs. All he needs is his brother, his car, and evil to hunt. That is Dean’s happiness.
If you want another (fantastic) take on the Sam and Dean dynamic in Route 666, I would highly recommend sargraf's Brotherly Manlove PicSpam. She has some really great pictures along with a very interesting meta on what Sam may be thinking in the episode.