Now that I’ve watched enough TW with Sashi to calm down, I can answer this.
Warning: it’s long. Sorry.
I’ll admit: it was not my favorite episode. I was disappointed. And I HATE saying that, I hate it so much, because whenever a new episode comes on and I see posts where people pick out all the things they didn’t like, it makes me really sad. I always want to say, “CAN’T YOU JUST ENJOY THE FREAKING EPISODE?”
So yeah. I want to love every single episode of SPN, because it means so much to me and having “bleh” feelings about things that I love isn’t fun at all. But in the interest of complete honesty, I had a lot of problems with this episode. No, it wasn’t even the Destiel stuff. It was just the way they dealt with Dick’s death (Mother of All, anyone?), the way Bobby went psycho (even though he made the right choice in the end), the weird moment with Polly taking off her dress, and most importantly, the way it feels like it could turn into the Dean/Cas show with Sam stuck up above utterly alone. There were a lot of things I thought were fanservice or that made me just stare at the screen like “…Are you fucking kidding me right now? Did you seriously just do that?” (For example, the little Castiel forgiveness moment. I’m sorry, but forgiving the person who shattered the wall in Sam’s head? No matter who they are, I just think that’s completely OOC for Dean.)
Basically, when it ended, I was sort of in shock. Like…that was not my idea of a finale, you know? It barely even felt like a finale.
However.
I took some time to calm down and examine my thoughts after hearing everyone else’s theories, etc. And now that I’ve stepped back a bit, I can appreciate what I did like about the episode: how Bobby moved on with grace, how Dean stood up to Castiel, every Meg moment, how Baby is back, and the fact that this gives so much potential for Sam and Dean to fight for each other and once again learn that they are so much stronger when they’re together. I love how Purgatory looks like it will be fuckin’ scary, because actual horror was one of the things I missed most during S7. I love how the plotline we didn’t get in S3/4 - Sam pulling Dean up from Hell - could come into play.
There were a lot of negatives, yeah, but a lot of positives as well. And at the end of the day, I’m just going to look forward to S8 with an open mind.
Also I mean. If nothing else, we’re guaranteed an amazing gag reel over the summer.
I mean Dean is canonically straight. I just don’t think Sam and Dean’s relationship has anything to do with sexual orientation, that’s all.
Also my headcanon about their sex life changes constantly, anywhere from no sex to Howl!verse blood kink sex. I don’t ship it because of the sex aspect. I ship it because of their history, the army men and the Legos, and the Samulet, and “Winchesterland,” and Dean selling his soul because he couldn’t live with Sam dead, and how they’d rather save each other’s sweet bacon than save the world, and “It’s okay, Dean, it’s gonna be okay,” and etc. etc.
I read fanfic, obviously. I have a shit ton of headcanon about their sex life. But I also have a shit ton of headcanon where it’s just Sam and Dean and the Impala forever, saving people and hunting things.
Not to say that their relationship is platonic - far from it. It’s just that what I really love about this ship is their incredible bond, and I think that goes deeper than their physical bodies, or whatever sexual orientation either might have. So I kinda just don’t really concern myself with it.
No.
I just…I know it was Kripke’s original plan to end after five seasons. I know Season 6 was a little rough in terms of plot and with Soulless!Sam. I know Swan Song would have made for an incredibly complete, beautiful, tragic ending.
But even with all that, it’s just like. I would have to live the rest of my life imagining.
So Sam was in Hell. And Dean wasn’t. He was living an apple pie life, suicidal and out of his mind with grief because his little brother was spending eternity - eternity - being tortured by Lucifer, and Dean couldn’t do anything about it.
Dean would die alone. He’d stay with Lisa until the end, yeah, because that’s what Sam wanted…but he’d die alone. Sam, of course, would never die. Lucifer would never give him that, and Dean would know it. Dean would go to Heaven, which would be where? Him, alone in a field with a box of fireworks? Him in the Impala, empty passenger seat? Where is Dean’s heaven if Sam’s in Hell?
Maybe they’d give him a fake Sam. A projection, like the young Sam in in Dark Side of the Moon.
I really, really hope they wouldn’t give him a fake Sam. That would make it so much worse.
Meanwhile, Sam would be burning.
And that’s how it would end. That’s the only ending we’d ever get. We’d just have Sam jumping, and Dean going to Lisa. Blackout. We could only ever imagine what happened next, knowing that it wasn’t pretty.
Noooooo thank you.
I think they would be different people, with a very different dynamic. The entirety of Dean’s personality - his obedience to his father, his black-and-white mentality, his soldier habits - comes from John constantly telling him, Watch out for Sammy. Protect Sammy. And Dean trained so hard and was always so willing to lead a hunter’s life because he was the protector, the one who basically raised Sam, the one who remembered Mary, and remembered her as something worth fighting for. So if Dean had all that taken away, and never needed to step up to the plate and be daddy’s little soldier, he would be vastly different. Almost unrecognizable, probably.
Even when we saw his soft side during DSotM, when he saw his mom again, he was smoothing things over. “Cleaning up after Dad’s messes.” Dean has never been the one taken care of. He doesn’t even know how to deal with that: there are a bunch of examples, but the one I remember off the top of my head is in The Girl Next Door, when Bobby reaches out to pat Dean’s face and Dean just looks like this:

He has no idea how to react to that. He doesn’t know how to handle being taken care of.
As for Sam, he would become more like the Dean we know, I think, though he’d still be more of a gray-area type person, and I think he would still be more rebellious towards John than Dean ever was. But while Sam is more reluctant about the hunter’s life, if he’d been needed to take care of his little brother, he would have done it. I think - and I truly do not mean this as emasculatory or whatever - he would have been more motherly almost? Like, instead of Dean’s “Buck up, kiddo” kind of thing he would be more open and “Let’s talk about it.” I’m not saying either way is better. Just that’s how I think he’d be as the big brother, more maternal.
Anyway, sorry this is so long. But to wrap it up: I absolutely think they would be different. We’re shaped by the roles we step into out of necessity. Sam and Dean, had they stepped into opposite roles, would not be the Sam and Dean we know.
(I talked about this a bit here as well.)
(THIS IS SO LONG I’M SORRY BUT YOU SHOULD REALLY KNOW BETTER THAN TO ASK ME ABOUT MY FEELINGS OMG)
…anyway
It is absolutely a painful season for me to watch, because both of them are in a lot of pain. Sam has this awful addiction, which to him is basically confirming all the thoughts he’s had about himself for his whole life. “I’m a freak. I’m a monster.” He hates himself for wanting the demon blood. But at the same time, he’s becoming so powerful, and he can exorcise demons without killing the host…which is a good thing, right? So he has these feelings of “oh God I’m a monster” and also “Why can’t Dean just understand that these powers are for the greater good???” and there’s confusion and the loneliness of deception and the anger at his brother and the world, plus the side effects of the demon blood. So Sam is not in a healthy place.
As for Dean, he’s terrified. His brother is obviously lying to him, something horrible is obviously going on, but he can’t figure out exactly what. Then when he finally does learn what Sam is doing, it’s in the worst possible way: he sees his brother completely lose control and feed on a demon. So Dean is angry that Sam was lying, scared that Sam is spiraling into darkness, and on top of this there’s the whole thing with Lilith and the end of the world, mixed with Dean’s constant flashbacks and memories from Hell.
So neither of them are stable emotionally/mentally, and a lot of that pain is stemming from the rift that is coming between them.
However, I don’t think that the love they have for each other seems less than ever. Exactly the opposite, in fact. They may be scared and resentful and frustrated and they may hurt each other in the worst possible way, but it’s because they love each other so much that they feel all those things. Dean is terrified that his father’s words are coming true, that he can’t save his little brother after all. Sam is furious that his old brother doesn’t get that what he’s doing is a good thing, finally a good thing to come out of all this darkness. They both want the other to understand. And this isn’t just your normal sibling rivalry - again, in addition to all that crap, there’s also, y’know, the end of the world. An unimaginable amount of stress, dropped on top of all these raw, negative feelings towards each other?
Boom. When the Levee Breaks. The people you love most have the most power to hurt you. That’s what that episode is. It’s their worst fears coming true. It’s two brothers who loved each other and betrayed each other.
As for the impacts on their relationship…obviously there were tons of trust issues (resulting in them separating for a while, although as we saw in The End, Sam and Dean not being together = bad idea) and a ton of leftover guilt/pain/anger/sadness/every bad emotion ever. But honestly? In the long run…it didn’t actually have a gigantic impact, in my opinion. I already wrote about why in the post I linked to in the beginning of this answer, so I won’t go into it. Quick summary: SPN is a story about Sam told through Dean’s eyes. It’s a story about how a boy sacrificed himself to save the world because he loved his brother. (Swan Song montage.)
Ultimately, what happened in S4 did not affect that outcome. It didn’t make Sam love his brother any less, or vice versa. Sam still jumped into the Pit, and it was still because of Dean. Therefore, nothing much changed.
So yeah. Man this is long, I am so so so sorry. But I hope this answers the question…
I think that he did the right thing. He handled the regaining of his memory in the best possible way - by acknowledging that he had done something terrible, and then trying to fix it. And I think that he was very brave, because saving Sam obviously landed him with Lucifer. I was reminded of the Castiel we met at first, and I’m not just talking about the social awkwardness.
Here’s the thing. I loved Castiel in the beginning. He had spent millennia obeying a God he’d never actually seen, and now he was rebelling because he found people he cared about. He finally had something worth fighting for.
I loved the Castiel who fought for his friends, even if it meant disobeying. I started hating Cas when he started doing things that hurt and betrayed those friends, the ones that had given him purpose and freedom. When he broke Sam’s wall, that was it.
I still think Castiel can never be a true friend of the Winchesters again. When Dean said “All our friends are dead,” it had a double meaning. Cas may be back, but the Cas they knew is gone, irreparably broken. And I don’t pity him. He got what he deserved. You reap what you sow.
However, he got what he deserved because he chose to save someone he’d hurt - at his own expense. Even though he could have just disappeared. He remembered the meaning of friendship and family. And for that, I am grateful.
No, I don’t think he really…cared about Dean. The love between the brothers isn’t at all related to their bodies, their “vessels” - they could be in any shape, any form, and still love each other the same. They’re soulmates - it is Sam’s soul, all of his soul, that loves Dean. During Soulless!Sam’s whole story arc, the part of Sam that loves Dean was being tortured in Hell.
However. I do believe there was a part of Soulless!Sam that…wondered. That sort of knew, inherently, this is what I am supposed to love.
When a soul as powerful as Sam’s leaves a body, I’m sure there’s some sort of residue, if that makes sense. Some sort of small essence left behind, and I think Soulless!Sam picked up on that. It’s why he smiled at Dean when Dean was holding the shapeshifter baby, why he tried to comfort Dean after the alien debacle (even if he kinda failed).
Yes, some of it was an act, but some of it went deeper than that. Some of it wasn’t Soulless!Sam being like, “Okay, gotta keep up appearances, gotta do x, y, and z so he doesn’t suspect anything,” it was “Maybe if I do x, y, and z, I’ll understand what Sam’s emotion over this person was all about.”
I think he wanted to get his soul back because…hm. I think he was jealous of Dean’s love for “Sammy”, almost. I don’t think he would have realized exactly what the jealousy meant, but when he said:
“Dean doesn’t care about me. He - he just cares about his little brother, Sammy, burning in Hell. He’ll kill me to get that other guy back.”
There’s a definite sort of wistfulness in those words. If Soulless!Sam truly didn’t give a shit about Sam and Dean’s bond, he would have just been like, “Oh, whatever, Dean doesn’t care. He just wants ol’ teddy bear Sam back. I don’t have a preference either way.” But instead he says Sammy. Dean’s little brother. Dean’s little brother who he’d kill for, die for.
Soulless!Sam is often portrayed just as a snarky asshole, but I personally see him as an incredibly tragic character. What would it be like to go through life seeing all this love, all these bonds, all these people fighting for each other, and have no idea what it was like for them? To know there’s something horribly, inherently wrong with you, and be unable to fix it? To have to act normal every day of your life? To spend every single waking moment with someone who’s supposed to love you more than anything, but has nothing but suspicion and confusion and dislike in his eyes?
If it were me, I’d be screaming, “Why am I not good enough? I look like him, I sound like him! I can’t help that I’m like this! Why do you hate me so much?”
And that’s why I have a soft spot for Soulless!Sam. And that’s why I think he wanted his soul back, up until the end. I think he was in a lot of pain, honestly.
Also, this just occurred to me. So Sam’s Dark Side of the Moon memories were all about his brushes with freedom, right?
Well, in Swan Song, again - I think we saw his true best memories. The strongest and most powerful. But…weren’t they just the same thing? Those memories of Dean gave Sam the ultimate freedom: the strength to overcome Lucifer himself, when Sam was locked inside his own mind.
Basically, Dean gave Sam freedom. Absolute freedom. And yes, it led to Sam’s sacrifice, which led to the Pit. But God, thinking about it now, it was almost like once Sam had been able to overcome that final test - defeating his own “dark side,” defeating Lucifer!Sam - it was like…he was good. He was set. He’d found freedom, tasted it, and it was enough.
And so he jumped.
Hm…this is actually pretty complex, because on the one hand, I want to say “Yes, the angels were just messing with him. Sam’s best memories are with Dean, being protected by Dean, etc. They’re aren’t the times when he was away from his brother.”
But the thing is - you can’t view those memories as being away from Dean. Because that’s not what it was about. The Thanksgiving dinner at his middle school girlfriend’s house, the place with Bones the dog where he ran away to for a couple weeks…those weren’t what I would have expected, because we all saw what made Sam regain control of Lucifer in Swan Song: Dean. Memories of Dean in the Impala when they were little, and so on. Those, to me, are sort of Sam’s core.
But outside his core, we have to think about what Sam’s personality is. He spent his entire life wanting freedom. From his father, yes, but also from himself. From being a freak, from being that kid who never fits in. In Dark Side of the Moon, we saw Sam getting freedom. In the Thanksgiving scene, he was surrounded by normalcy. In the Bones the dog scene, he was alone.
Sam: Maybe that’s what Heaven is. A place where you relive your greatest hits.
Sam’s greatest hits aren’t about escaping Dean, leaving Dean alone with John. They’re about fitting in. Having a real, normal Thanksgiving like a real, normal person. Being on his own for two weeks, with no one to judge him or be disappointed in him. That’s all Sam craves.
So yeah. While I don’t necessarily think the memories we saw in DSotM are Sam’s absolute best memories, which we saw in Swan Song, I think they are definitely some his greatest hits and fundamental to his character.
It’s so interesting to think about the different facets of Sam and Dean.
Like…sometimes they’re “Bad Day at Black Rock,” they’re “Changing Channels.” They’re goofy and brotherly and rebellious. They bicker in the Impala and tease and bitchface and dress up in cowboy outfits, and they kill some evil sons of bitches along the way.
Then they’re also completely broken. Alcoholic, crazy, hallucinating, emotionally destroyed, suicidal, exhausted, dying from the inside out and the outside in. They’re like twin cities razed to the ground by so many bombs.
Then there’s the side I sometimes forget: these boys are serial killers. They are. Sure, they’re killing demons, but they’re killing people too, and somewhere along the road they had to either hang themselves or stop caring about it so much. They leave strings of bodies behind them. So many crime scenes surrounded in yellow tape, leaving police officers in dozens of small towns absolutely baffled.
Sam and Dean may have their goofy moments, they may have their broken moments, but they’re fucking dangerous. They’re the Winchesters, built out of blood and fire. They’re the worst nightmare of so many things, human and otherwise. They are the ones you want protecting you. They’re also the ones that sort of scare you shitless even as they save your life.
It’s so strange and wonderful. They’re terrifying, they’re unstable, they’re killers, and they make you love them so much you cry over it.