Dean is jealous. He isn’t sure if it’s because Cas is so focused on Jimmy, his intense blue gaze Dean was so used to being the only recipient of, now shared with another person. Or if it’s because he can’t walk up to them both and join in on this unique, incomprehensible intimacy.

Jimmy? The passionate, determined man, who wished so desperately to be someone greater? Who, despite a lifetime of devotion, stood up to the forces of heaven and hell beyond his comprehension because he came to believe it was the right thing to do? A simple man, who jumped straight into danger to protect his family against pure evil? The one who sacrificed his body, mind and soul forever just so his daughter could have a chance at life?

This is not an issue until Metatron steals his grace.

Other ideas I’ve been thinking about:

• Cas stares right through Dean in Jimmy’s body, making him believe all angels behave that way in vessels. Until he meets Uriel and realizes something is up with Cas in particular.

• When Cas is forced out of Jimmy in The Rapture, Jimmy is disoriented and terrified, realizing the angelic sight Castiel granted him is gone.

• Jimmy is still able to make it to his family on his own. He has been blind for longer than he had angelic sight, and he wasn’t going to let that loss stop him from seeing his family again.

• Jimmy is able to sense that Roger is a demon before he reveals himself, because he can smell the sulfur on him. Perhaps the same happens with Amelia later on.

• When Cas is low on grace, he is still able to see through his angelic form, just not as broadly as he can at full power.

• When his wings are damaged in the fall, a part of his true form’s eyes are as well.

• If you think Jimmy was terrified finding himself somewhere he couldn’t recognize with no sight, imagine how it would be for Cas.

• Cas can’t see the fall of the angels, but he can feel the burning grace on his face.

• He still instructs Dean to look after Sam instead of coming to get him on the phone. He doesn’t mention the blindness. He doesn’t want to burden Dean when Sam needs his whole attention.

• He barely makes it to the bunker, relying on the kindness of strangers to help him get where he needs to go. It is so much easier for April to trick him this way.

• I can’t imagine Dean kicking Cas out of the bunker when he finds out Cas is human and blind. He bargains with Gadreel to let Cas stay at least a few days to adjust. But I do think Cas would leave voluntarily if he found out there was a danger to Sam’s life, perhaps sneaking out at night.

• Cas feels incredibly compelled to still be useful despite his human disability. While at the bunker, he studies the area meticulously, maps out the entire perimeter in his mind, practices his blade skills even harder, as he is unable to learn to shoot.

• If Cas leaves, Dean goes to find him immediately. Eventually, he does, but Cas refuses to come back as long as Sam may be in danger. Dean accepts his choice, but promises to keep checking up on him regularly. He does, coming to where Cas is staying way too frequently, worrying sick. Cas struggles at first, but adapts to his disability with time, and eventually starts doing well for himself, perhaps still working the same job at Gas-N-Sip.

• Cas has a freakishly good memory of where everything is. Both a remnant of his angelic abilities and a personality trait, in my opinion. Helps that he is extremely determined to memorize the area, too.

• Another angel’s grace is able to help him manifest his true form again, but its vision, hearing, senses all feel wrong. The colours are all wrong, the vision is fuzzy and blurry and static-y all at once, the grace constantly fighting against him. He finds that closing his angelic eyes and relying on his body’s senses, as he did as a human, is way better than trying to battle against the wrongness of the grace.

• Cas never learns how to drive.

What if Cas kept Jimmy’s ring all this time? Making sure that, no matter what, it doesn’t fall out of his trenchcoat pocket. As he becomes human, before discarding the ruined coat, with the wallet, he also takes out the ring and carries it with him, unable to leave behind a piece of the man who sacrificed everything for him. Maybe, when he has a hard time surviving as a human, he reaches into his pocket and clasps the ring in his palm, silently asking Jimmy for guidance on how he could go on.

Maybe he forms a habit of fiddling with the ring whenever he’s feeling anxious, or confused, wishing he could ask Jimmy how to help Claire, wishing her father was still here.

When he realizes his feelings for Dean, he stares at Jimmy’s ring for a long time, wondering how it felt for Jimmy to love Amelia. Did it feel like this? How did he deal with all these overwhelming feelings? He hopes Jimmy and Amelia are in heaven together, happy. He wishes he could have given them that happiness on earth.

When he dies, and Sam and Dean burn his, Jimmy’s, body, the first thing he checks as The Empty releases him is if the ring is okay. Thankfully, it’s inside of his new coat, although once he learns the original burnt, he wonders if it is even the same one. He cherishes it all the same.

He wishes Jimmy could be there to help him be a good father to Jack. He thinks Jimmy would have been so good to his son, just as he was to Claire.

Lore-wise, and from 4x01 alone, it makes sense for Cas not to be in a vessel at the time. Angels don’t need vessels to smite demons in hell, and I don’t think a human soul without a body — Dean — would be hurt from seeing an angel’s true form (probably).

Let’s look at the timeline. Assuming he had no vessel. Cas rescues Dean from hell, which took around 40 years, or 4 months on earth, depending on how soon the angels were dispatched. When raising him, Cas left a handprint on Dean’s shoulder. But if it wasn’t Jimmy’s hand, can we assume maybe his true form has human hands, or his grace adopted a shape of a hand? That’s possible. Then, as Dean digs his way out of the grave, immediately, Cas tries to contact him in his true form. He does it twice. When it doesn’t work, he goes to search for a vessel.

Now here is where my question lies. From the last time Cas contacted Dean, and till the moment Dean and Bobby went to summon Castiel, it must have been just a few hours. All in the same day. Then, did Cas search for a vessel in those few hours? In the deleted part of Cas’ first appearance, he says to Dean that finding a vessel strong enough to contain him is hard, that’s why he didn’t appear to Dean in a vessel earlier. Meaning he was finding a vessel during those few hours (of course, deleted scenes shouldn’t be taken as 100% canon, but I thought I should mention it).

Yet, this timeline falls apart when we see Jimmy’s perspective in 4x20. In the episode, we find out that it took a few trials and talks for Cas to deem him “worthy”. First, it’s through the TV when he has a seizure, and Amelia runs into the room. It’s dark outside. Next time it’s through the radio, and Jimmy can understand Cas. Then it’s the boiling water test, and Amelia comes home, seemingly from grocery shopping. It’s daytime. Next scene is Jimmy talking to Amelia in the evening, saying Castiel has talked to him a dozen times already. Amelia is concerned and tries to persuade Jimmy to take his pills. The fact that he already has medication suggest that, in-between the boiling pot and that conversation, Jimmy must have gone to the doctor and gotten a prescription. Furthermore, Amelia seems very exhausted by the conversation, and even threatens to take Claire away if Jimmy doesn’t get help. To me, this seems like a conflict that has been going on for a long time, maybe weeks or months. You don’t just walk away from the person you love with your child lightly.

So the question is, did Cas possess Jimmy before hell, after all? Then, did he go to hell in Jimmy’s body, and is it really Jimmy’s handprint on Dean’s shoulder? Or did he leave Jimmy behind, and only emulated the human handprint with his grace? After Dean was rescued, did he purposefully leave Jimmy’s body in hopes that Dean would be able to perceive his true form and voice? If so, what was Jimmy doing that whole time? Just walking around? And if he was free all the time Cas was in hell, which was 4 months, what was he doing then?

In my opinion, the most likely possibility is that Jimmy had already been Castiel’s vessel before he went to hell. That would make the most sense. We can excuse the Jimmy wandering around thing by saying, well, maybe Cas was posessing him, but channelled his true form out of his body. Or he had Jimmy be asleep somewhere, or in a pocket dimension like one of Gabriel’s, while he rescued Dean/talked to him.

There’s also another possibility. Maybe Cas had been preparing Jimmy to become his vessel before hell, but only took possession of him once he needed to talk to Dean? Jimmy says yes for the first time when it’s dark outside, which aligns with the time Dean and Bobby summoned Castiel. But then, isn’t it one hell of a coincidence that Jimmy decided now was the time to say yes to angelic possession, right when Cas needed him? And that would also mean Cas hadn’t spoken to Jimmy in four months, as he was in hell during that time. If you ask me, four months without an angelic voice in my head and dorky devotion tests would be enough to make me doubt if I truly contacted an angel, after all, or if everyone around me was right, and I was delusional. But Jimmy was very sure of himself even by that time, like Castiel hadn’t taken such an extended break from contacting him.

An only child to religious parents.

His parents weren’t extremely strict, but demanded good behaviour, good grades, obedience.

Undiagnosed neurodivergent — I’m leaning towards ADHD. Because of that, he struggled to live up to his parents’ expectations: pay attention in class, sit still in church, make friends. Got routinely reprimanded, despite trying his best. Because of that, developed a tendency to people please and blame himself, struggled to stand up for himself.

Went to a religious school, then applied to a college his parents insisted on. Studied hard for the first year, struggling to socialize and make many friends. Away from home and alone, his mental health worsened, and at some point, he decided to stop following what people expected from him and rebel. Said rebellion was not as out there as Jimmy wanted though — he ended up just taking more breaks, going out with his classmates, sleeping in sometimes, even missing church (blasphemous). Basically just normal college life. He couldn’t bring himself to do more.

Had many doubts about his faith as a child and young adult, but always ended up repressing them. The most he let himself admit his doubts by that point was during his “rebellion”.

Met Amelia in college. She was devout, more than him, and for her, Jimmy decided to dedicate himself to his religion once again. The rebellion was officially over.

Roger (Jimmy’s best friend that got posessed) was initially Amelia’s friend who Jimmy got to know through her. They all became best friends, and from then on, the majority of Jimmy’s social circle was Roger and Amelia’s friends.

Though Jimmy drank in social situation, he didn’t enjoy alcohol as a whole. It had a weird effect on him, so whenever he could, he avoided drinking entirely. Roger thought he was just a coward, mostly because none of them understood Jimmy’s neurodivergence (they noticed he was different in some things, but lacked the knowledge to really explain it), plus the time period. Only Amelia really believed him.

Had a complicated relationship with food, as food being taken away was used as punishment in his childhood (this one is taken from @alices--angel , I really liked this headcanon. Go read their headcanon post!)

After graduating, him and Amelia got married in a church with mostly Amelia’s friends and family present. Jimmy’s parents were invited, but none from his extended family.

Jimmy’s parents loved Amelia a lot, but Jimmy was always cautious introducing them. He didn’t realize why he felt that way, he just knew he did.

After the marriage, they moved away closer to Amelia’s parents, and Jimmy essentially went very low contact with his parents. He blamed himself for that, not realizing why he’d done that in the first place, but as he stepped into his and Amelia’s new home, it was like he could breathe for the first time.

Jimmy had always wanted children, so when Claire was born, he was so, so happy.

He used to have a higher-paying job, but at some point, he got fired. It was not his fault, but Jimmy blamed himself anyway. But on the outside, he acted avoidant, refusing to talk about his feelings. He felt like he didn’t deserve Amelia’s sympathy. This was the first thing that drew a wedge between him and Amelia.

Jimmy got a low paying job in ad sales. Amelia encouraged him to search for a better job, and at first Jimmy did, but after being rejected many times, he got discouraged. Besides, despite the new job not being something he was proud of or really enjoyed, he liked being able to have more time at home. He got to spend more time with Claire, he got to cook for his family, and Amelia’s income was mostly enough to support them. Nevertheless, his own and Amelia’s taught belief was that, as the husband, that role wasn’t suitable for him, and he should still strive to get a better job. For Jimmy, that belief fed his guilt, and for Amelia, it fed her frustration with Jimmy.

Jimmy enjoyed cooking. He loved getting to feed his family, provide for them, especially after not having food security in his childhood. He wasn’t the greatest at it, but making fun meals for Amelia and Claire was one of his favourite hobbies. He was usually the one to prepare all their meals. (This headcanon stems from the hand boiling scene where Jimmy cooks pasta before Amelia gets home, and Amelia’s sandwiches for lunch after Jimmy comes home from being possessed).

He was Claire’s favourite. He spent more time with her, and because he never fit in by nature, Claire felt safe to express herself with him like she couldn’t with Amelia.

Jimmy was closeted bisexual. He never let himself do anything with that knowledge, or even entertain the thought of a relationship with men, therefore he never managed to realize it himself.

Despite the church’s teachings, Jimmy was not really homophobic. It was more so that he never had the chance to be confronted by the topic head on. He met some non-straight people in college, but only spoke to them briefly. He never believed those people to actually be as sinful as the church stated them to be, but just as he did with all his doubts, he repressed those questions too. In fact, he felt a strange kinship with those people. Him and them were both “weird”, not just because Jimmy was closeted, but because he was not neurotypical, and so to admit they were sinful was to admit Jimmy himself was, too.

Jimmy’s marriage, and his faith, were beginning to fracture by the time Castiel contacted him. Him and Amelia were drifting apart — Jimmy kept reassuring Amelia he would get another job, but never followed through, and Amelia was growing more and more frustrated. Jimmy couldn’t admit that wasn’t what he truly wanted, and Amelia couldn’t understand what was wrong. Jimmy began to skip church, claiming to be feeling unwell, making all sorts of excuses. He spent more time away from the religion, and that made all his repressed doubts resurface. He began to realize many of the things he’d done with his life were not his true desires, but wishes and expectations of the people around him. He yearned for something more, something to make his life feel like his own. For it all to make sense.

When Castiel arrived, Jimmy was so quick to follow him in most part because his existence solved so many of his problems. The existence of angels cleared any of his doubts. Following a mission from God would make Amelia proud of him for his faith, for his devotion — he would be making it up to her for all the times he failed to be a devout man, it would help them be close again. And lastly, being needed for something so grand and holy proved that Jimmy wasn’t broken. He was worthy of God, and he was worthy of something great. By doing this, he could atone for all his (perceived) failings.

Jimmy could hear and see Castiel’s true form (this is semi-canon). I like to believe it was one of the reasons Jimmy was so convinced and enamoured by him. Who else could be so magnificent and glorious but a true angel?

This one is for my jimstiel loving side — Jimmy had almost a crush on Cas. He let himself feel it because angels were not technically men or women, therefore it was not bad to feel this way, right?

Jimmy and Cas talked for months before the possession, long enough for Jimmy to get prescription medication for his “delusions”. Perhaps Cas tested him a lot more, giving him tasks to complete. Maybe he told Jimmy of his past battles, of heaven, his siblings, God. Maybe Jimmy shared his own life with Cas, giving the angel the first true glimpse of humanity. So many things could have happened.

Getting a glimpse into an angel’s mind shook Jimmy’s worldview to the core. Suddenly, so many of his beliefs felt meaningless, as angels themselves never even followed them. It was so much easier to accept his doubts after that and renounce heaven for his family. Even under threat of divine punishment, it was not worth it when even the beings he thought were good and holy turned out to be corrupted.

Jimmy knew Castiel had doubts. And he hoped the angel followed through with them. In the end, the only thing he held against him was failing to keep his family safe.

Claire is believable. Trauma changes people, especially children. When we first meet her, she’s quiet, timid, polite. But after losing both of her parents, she lashes out at the world, at Castiel, at her mother and the forces that took everything away from her.

Amelia is different. She is someone grounded in reality. Despite witnessing with her own eyes that Jimmy’s hand was completely fine after being submerged in boiling water, she doesn’t let herself slip into the belief that it was a divine miracle. She begs Jimmy to get help, no matter how much he tries to explain. When she realizes her husband isn’t going to budge, she makes an ultimatum to take Claire away, believing him to be a danger in his current state.

When Jimmy comes back a year later, we find out they’ve stopped looking for him. Amelia isn’t all that sympathetic towards Jimmy. She is angry that he never kept in touch. She doesn’t allow him to see Claire. She says their relationship can’t be the same. Very reluctantly, she allows him to have dinner together.

Now, after their neighbours get posessed, we aren’t sure if Jimmy was actually talking to Amelia or to the demon. “Amelia’s” insistence that they can’t split up again hints towards the fact that the demon might have been trying to keep Jimmy close so they could grab him once the Winchesters drove away. This is further supported by the fact that the demon then slaps Claire in anger and points out how “it’s just not my day, is it?” Implying they were trying to keep Jimmy from getting away.

After that, we only see actual Amelia run to check over Claire after her being posessed by Castiel, despite her husband bleeding out on the floor. Now, you could make an argument that she was frozen in fear at the sight on an angel posessing her daughter. Understandable. Yet, when Jimmy is re-posessed, Amelia makes no move to chase after her husband, try to get him to stay, talk to him again. If you believe it was truly Amelia, and not the demon, who said they shouldn’t split again in that car, those actions make even less sense. Plausible deniability here is that, once again, seeing an angel in the flesh is very intimidating. But alternatively, that could mean Amelia has moved on. She’s accepted the fact that Jimmy is gone. He was not the same person anymore, and chasing after him would be pointless.

If it was indeed the demon in the car, that would mean that the last time we saw actual Amelia speak to Jimmy was when she tried holding him back from hammering their “neighbour” to death. She never took back any of her previous words. We don’t know if she changed her mind on giving Jimmy another chance after finding out angels and demons were real.

Now, we flash forward to season 10. We find out Amelia has abandoned Claire at her mother’s. She has been searching for Jimmy tirelessly for years. So long, she lost sight of what was important — taking care of Claire. She is grief-stricken. All she wants is to find Jimmy.

Now, that seems like a very drastic shift to me. Once again, plausible deniability: maybe, after she got over her fear of angels, she realized Jimmy was way too important for her to let go. But we also can’t forget the fact that Amelia from season 4 comes across like an extremely different person. If you asked me to describe what I thought Amelia was doing before we found it out from canon, I would have said she moved away, settled down somewhere quiet with Claire, enrolled her in school, found a quiet job. Maybe found love again. Season 4 Amelia feels like someone who is ready to let go of things out of her control and prioritize what is more important to her, mainly Claire and her wellbeing.

Of course, season 4 Amelia is a character that appears very briefly. There are many holes to fill with her character, and the writers did just that by giving her a different path to follow than what we may have expected. It wasn’t a wholly unbelievable route for her to take, but it also wasn’t entirely supported by what had already been established for her character. At least in my opinion.