What your favorite head canon for Dean, Cas, Sam, and/or Jack?
I had to think about this for a bit! I have a lot of head canons I really love and picking my favorites is hard. So I've got some lists. With both silly and serious head canons:
Dean: I do really like the gay Dean head canon. Dealing with comp het and preformatting heterosexality/masculinity is such a heartbreaking story to explore with Dean.
(Bonus: Mary is a lesbian also dealing with comp het. She never really liked men, but there was something about John that made her go for it. But no other man really did it for her. Ketch was an attempt at normalcy.)
If he wasn't forced into hunting then Dean would have been a teacher. We've seen how he interacts with kids/teens and he's always trying to teach them something. I, specifically, think he'd be a literature teacher because of his love of not just books- but other little references he makes to media.
Dean is That Guy(tm) who 'hates animals' but then will go out and buy the poor dog a hamburger because he's just so hungry. He says he doesn't want a pet and an hour later he's got the cat in his lap as they watch tv (he has taken his allergy meds). But remember, he hates animals.
Dean names objects he's attached to. That includes his favorite gun, his favorite spatula, and favorite knife. (And his car)
Dean has ADHD.
Sam:
Sam doesn't actually like veggie bacon. But Dean made a big deal of buying it one time, and now he will be eating and pretending to enjoy it.
Before Mary came back to life, if someone asked him to describe his mom his first impulse is to describe Dean. It's who he pictures when he thinks of a mom.
Later seasons Sam DID work with Rowena to get witch powers- but the show just never showed them to us. That man is a witch.
Amelia, from Season 8, was never real. Sam really did have a mental breakdown.
Building on that, Sam's blurry wife is blurry because she's a siren that can't figure out what Sam wants. Dean Jr. Isn't real either.
On a less sad note: Sam is That Ally(tm) that took one gender/queer studies class in university and now thinks he knows everything.
Cas:
Cas has had feelings for Dean since he pulled him out of hell. He didn't understand them until around the end of Season 5. Knowing that Dean didn't give into Michael made something click for him.
Cas is a pocket hoarder. He just has all kinds of stuff in his pockets at all times. You need a dressmaker's tape measure? He has one in his coat pocket. You need a dog collar? He's got that too. He just finds lost items and takes them with him.
Cas likes bees, but his favorite animals are cats. He likes being able to pet their fur. The texture is nice under his hands and it helps him when emotions are a Bit Much.
Cas is autistic.
Cas' favorite TV is trashy reality shows. He doesn't understand why anyone would watch them- but he keeps getting dragged into them. There's something about them that just. Makes him keep coming back.
Nonbinary Cas! I have a 7K word wip about nonbinary Cas because it's so important to me. Yes, he's gender fucky in an Angel way, but also in a human way. Even if he's human he just doesn't feel male or female. He's just some third thing (agender/gender fluid/???).
Cas' favorite sex position is 'anything that lets me look into Dean's eyes'. (He doesn't have a preference for top or bottom or anything. As long as it's Dean AND he gets to look into his eyes).
Jack:
Jack is vindictive when he wants to be. He's normally kind, but when someone hurts his family he will find a way to make them pay.
Jack is nonbinary, as well. He just doesn't understand why gender even matters. There are much more important things happening.
Jack's favorite Disney movie is The Little Mermaid II: Return to the Sea. There's something about the main character being half human and feeling like they don't fit in with others that really hits him deep.
Jack did make himself look like a combo of Cas and Dean on purpose. He wants to look like his family.
If he had to have a legal name, he'd want Winchester as his middle name. He wants to keep his mom's name as his last name, but wants that connection to the rest of his family, too.
That's all I've got for the moment! My head canons kind of change with the world- so if I'm doing an AU then I'll adjust.










