The episode Exile on Main St. (named after a Rolling Stones album with some familiar titles like ‘Torn and Frayed’ and ‘Soul Survivor’) begins with a shot of Dean Winchester in some kind of internal pain, awake before his alarm clock goes off. He’s not a happy camper. He seems hollowed out.
Between this scene and him screaming the words “Good for who?” to Bobby after the latter told him that it was better for him to be out of the life with a woman and child and not be dead before the age of thirty, we start to realize that Dean is far from alright.
Bobby Singer did not know what Chuck had told us at the end of Swan Song: that every fiber in Dean’s body either wanted to die, or to join Sam in the Cage. These are two different things, wanting to die and wanting to join Sam in the Cage. Dean explicitly tells Bobby that he went to Lisa and Ben because Sam asked him to. It was not what he wanted. What Dean Winchester wanted, was to die.
But between these scenes, we see something interesting. We see Dean’s routine in Suburbia: breakfast for Ben, packing and driving for work, working construction, beers with his neighbour Sid while ignoring the woman he’s shacked up with, teaching Ben how to fix a car, checking the house and locking up at night, drinking whiskey, and glancing out of the window to Sid’s house to Sid having wine with his wife and turning away as though the scene causes him pain.
Why does the scene of his neighbour with his wife cause Dean Winchester pain?
If the quaint suburban scene was something that Dean desired, all he had to do was grab a couple of wine glasses and find his woman upstairs. It’s not the scene that caused him pain.
He had a crush on Sid’s wife, then? Sid’s wife is nothing to him, we barely see her. Sid’s wife isn’t important.
What it is that causes Dean Winchester pain as he glances out of his window to his neighbour’s house – and we are lead to believe that it is every night he does this – is Sid himself.
So, we come to a scene of Dean and Sid sitting in a bar. This is an important scene, it follows directly after the cold open. They do this often. Dean has been living in the neighbourhood for a year. Sid tells Dean that he has been buying him beers for a year. It’s normal if you buy a guy a round now and again and he returns the favour, even steven. But that’s not what Sid says. Sid has been buying Dean beers for a year.
Let that sink the fuck in.
Intense eye contact, licking of the lips, just another day in the life of Dean Winchester.
Dean also does not look at any of the sexy, scantily clad waitresses in the bar. He’s there for Sid. He’s there for Sid with the very blue eyes who also has some kind of past that makes him not fit in to suburbia. He affirms Dean. He thinks Dean is the bee’s knees. He’s willing to sit down and have a drink with Dean Winchester, and from what we can tell, does it often.
We see the El Sol sign behind Sid. The sign we saw behind Gary the teenage witch headed to MIT in Swap Meat who was fulfilling a role similar to Sid’s. A role similar to Nick the Siren in Sex & Violence. The sign that has been attached to his sun, Ash-shams, in every one of its appearances for the past four seasons. It might just be co-incidence, though.
But do you remember how in the end of Swan Song, Castiel asked Dean whether it was peace or freedom that he was looking for? Well, next we see Sid wearing a winged Nirvana shirt. It’s there not only to tell us that Sid – like Gary and Nick – has a similar taste in music to Dean, but that nirvana – peace – is something that Dean desires.
Dean himself has but one wing.
While Dean was with Lisa, there was a side to him that was pulling him across the street to Sid. No, I don’t think he ever tapped that. He was pretty adamant about playing the part of 'being taken’ as he shredded the phone number given to him by a Djinn at the bar (but note also that he made sure his friend knew that he was faithful, not that his lady friend knew). But we see him look out of the window to Sid’s living room wistfully, and it becomes obvious that he desired something from Sid. Also brotherhood. Also friendship. Because Sid also looks like Sam and Castiel.
But that was not the only thing he wanted. He wanted companionship.
The Djinns were there to get revenge on Dean Winchester specifically. They wanted to hurt him personally. Dean got Lisa and Ben out of harm’s way by sending them to Bobby. But instead of coming at Dean and Sam, the Djinns decided to visit the neighbours and kill Sid and his wife instead.
Sure, the Djinn saw Dean with Sid in the bar, but why would they think killing Sid would hurt Dean like killing Lisa and Ben would have hurt Dean?
Regardless, as soon as Dean sees the Djinns attack Sid, he throws all caution into the wind and rushes in to try and save him. Alas, too late. Sid is killed. Bye, Sid. We hardly knew ye.
I do feel obliged to point out that Dean rushing to the body of Sid has a parallel in a little episode called I’m No Angel. You know, the one where he sees April stab Castiel. So we can conclude that Castiel is like a neighbour to him. Or we can conclude something else.
Note also that it is Azazel, the Yellow Eyed Demon, that the Djinn poison makes Dean hallucinate. Not Lucifer who killed Sam a year previously. The Yellow Eyed Demon, who in his hallucination gets Ben-(Sam) addicted to Demon blood and burns Lisa-(???) in the ceiling, surrounded by stars. That is the horror that Dean’s mind conjures up. That had been the most painful moment in his life, hell and high water.
In the episode, Lisa tells Dean that in spite of their difficulties, the time they had spent together had been the best year of her life. I always felt the negative space in Dean’s lack of answer to this, but thought 'But it was the worst year of mine’ would have been too cruel.
But as we remember that every fiber in Dean Winchester’s body wanted to die, or to join Sam in the Cage, the year he spent in Suburbia reveals itself as exquisite torture. Especially with Sid there across the road, in sight but out of reach.