1 - 20 of 1,368 Works in Dean Winchester Has Mental Health Issues
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In a world where John was wrong about demons killing Mary, Sam and Dean still grow up without a steady father figure, believing in a supernatural world that doesn't exist. Such a childhood brings on mental health issues, and by the time Dean is eighteen and Sam is fourteen, these issues are unable to be ignored any longer. When they are both institutionalized at St. Edlund's Psychiatric Hospital, they meet several interesting characters in the adolescent ward, and struggle to find the path to recovery.
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Apple Pie And Pancakes by Vanitas101hhhh
Fandoms: Supernatural (TV 2005), Supernatural (TV 2005) RPF
27 Jan 2026
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Dean Winchester didn’t expect Stanford to change his life — he just wanted a fresh start, a solo dorm, and maybe some quiet nights with Queen on full blast.
Instead, he got a roommate with eyes like the sea before a storm, a heart full of mystery, and the patience to see through his walls.
Between apple pies, pancakes, and late-night bickering, Dean finds something he didn’t think he deserved — peace. Maybe even love.or in short:
Dean Winchester’s college experience checklist:Move into dorm ✅
Argue with roommate ✅
Fall in love with said roommate ❌ (pending review)
He didn’t sign up for feelings, but Castiel Novak might’ve missed that memo.
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Dean woke up one morning and he had a dream in which he went through his whole life and he knew the ending of his life and Sam's life. So he decided to change his brother's destiny no matter what. Dean chose to disobey his father's orders and Sam got sent away. But Sam, as Dean's little brother, he also decided to disobey...
Chinese version is here（中文版链接）: https://archiveofourown.org/works/72101406/chapters/187694996
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Deam梦见了所有的一切。他决心改变Sam的结局，改变自己的结局。他决心与John对抗，为Sam选择一条正确的人生道路。只是，他没有想到，想要违抗命令的人，不止他一个。
英文版在这里https://archiveofourown.org/works/72100941/chapters/187693766 -
The Way to an Alpha's Heart is Through His... Stomach? by Supernaturalgirl67
Fandoms: Supernatural (TV 2005)
25 Jan 2026
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Omega Dean Winchester is a single father to his two pups Ben and Emma. He's wearing himself out trying to chase his dream and provide for his pups in expensive New York City. Castiel Novak, single father and hard working architect couldn't cook a meal to save his life. When he and his daughter get tired of takeout constantly, Castiel decides to hire Dean as his personal chef at his brothers recommendation. When instant attraction occurs, how long will it take for the two to pull their heads out of their asses and realize true mates aren't just fairytales in the books Castiel's mother writes?
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It's senior year and Castiel Novak isn't expecting anything exceptional to happen. He has his friends, his debate team, his family to drive him crazy, and only a vague idea on what the hell he's going to do after high school. When his brother's childhood friend moves back into town, the most Castiel can hope for is expanding his social circle by a person or two.
Dean Winchester didn't think he'd be spending his first year of "adulthood" still in high school and suddenly under his father's thumb again. He's trying to make the best of it, giving his all on the hockey team and looking out for his little brothers while fostering his newfound friendship with his classmate. Only thing is, the full on gay crisis he's having is throwing a wrench in his year.
Series
- Part 1 of Sounds of Someday
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[SLOW UPDATES]
—
"You ever sucked a man's dick before?" He asked out the blue, taking you by surprise. Dean doesn't even bat an eye in your direction, nor does he even clarify the reason he's asking.
"The fuck did you just ask me?" Your brows raised and your lips twitched into a frown. Dean sighs as if he's speaking to a five year old. His green eyes land on you with a serious glint in them. “You heard me loud and clear, sweetheart."
~
After the death of your father, you'd never expect for your mother to move on, even after a few years. Her new husband is someone you couldn't bring yourself to get close to, no matter how nice he seemed.
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notes: weekly updates! (sometimes twice a week), please read tags because this contains a shit ton of noncon towards the end. due to a lack of black!reader inserts, i have written and heavily implied that for the mc.
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The year is 2002, Dean doesn't know where he is or why Jack has suddenly become a baby, he's tired and the only thing he wants to know is who the idiot was who thought it would be wise to give wings to a baby!
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He just had to ignore the pout in Dean’s lips when he spotted a problem in a car, the way that those jeans hugged his ass just right, the way he wanted Dean to-
It would go away with time.
All he needed was time.
Time that would come to pass, and time that would grow like vines around his heart, entwining himself to Dean Winchester. Even when they returned to college for the beginning of their sophomore year, that little flutter of a butterfly in his stomach, now a swarm, remained.
He was fucked.
If having a big, fat crush on your best friend was wrong, Castiel Novak was most definitely not right.
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after sam’s death in 2060, dean and castiel disappear from the world.
what follows is decades of silence and drifting—two immortals moving through a world that has begun to forget them. dean, a vampire, struggles with the slow crawl of time and the crushing weight of outliving everyone he’s ever loved.
eventually, they stop running. a cabin. a quiet life. a stillness brings both peace and dissonance—until the past begins to echo forward again.
when family comes looking for them, bringing warnings of supernatural unrest and signs that jack’s heaven is slipping out of reach, dean is faced with the hardest question of all: what does it mean to keep living, when everyone else is gone?
PLEASE NOTE:
1) sexual content is indicated with a !, so feel free to just skip if desired
2) although all chapters will include trigger warnings where appropriate, any particularly difficult chapters will include a # as well
3) any chapters in need of some serious tlc that I haven't gotten around to yet will be indicated with a @
4) consequently, any new alterations will be indicated with a *Series
- Part 4 of night shift
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What happens when two brothers are too stubborn to apologize to one another before shit hits the fan?.
What happens when you leave a job half done unintentionally?.
What happens when a blast from the past appears in each individual Winchesters life?.
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Book Three in the Ripples In The Water series. This book will not make sense as a stand-alone, so please go read Book One, The Family Business and Book Two, Perdition first!
I'll be adding to the tags as we go along, so make sure to keep checking!
Series
- Part 3 of Ripples In The Water
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"Write about your favorite characters with your issues!" Ok.
Dean Winchester is sometimes not aware that he has a body. He forgets to take care of himself. He forgets he is human. He sometimes feels like a void of nothing but old memories and past trauma. He is no one. Sam convinces him he is someone.
- Language:
- English
- Words:
- 605
- Chapters:
- 1/1
- Kudos:
- 12
- Hits:
- 66
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After the fury comes the quiet, at least on the surface.
Everyone in their own room, everyone lost in their own thoughts.
Because a family that loves is never perfect, and when love runs too deep… mistakes are inevitable.
🫠🫂Series
- Part 33 of The Tragic Misadventures of Dean Winchester
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Right after Empty takes Cas away, Dean faces a moment of regret. The 5 stages of grief sink their teeth into Dean one by one. Regrets flood his brain. All Sam and Jack could do was to walk around on eggshells around him, witness him falling apart.
Lost love, lost friend, lost father. Grief ties hands with desperation.
Enjoy. Endure.Check me out on Tumblr: cloudofsmokes
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Apocalypse world Michael did his damage on Dean, He fought for his family, for Sam, but it became too much. One man couldn't handle such guilt, especially one as strained as Dean Winchester.
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Mama take this badge from me (I can't use it anymore) by ArousedRay
Fandoms: Supernatural (TV 2005), The Rescue - Nicholas Sparks
14 Jan 2026
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AU: Dean Winchester is a firefighter having to navigate the unexpected between bonding with a little boy and his mother to grieving what he once had.
Completed fic.
Based of the novel by Nicholas Sparks; None of these characters are mine and this story will reference play by play of both the book and the show so I don't claim all of this as my original work just something to do for fun please don't sue this broke college student haha (No fr)
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Human genders wasn't exactly something angels usually had to concern themselves with. Neither primary or secondary gender was of any importance to them.
Castiel thought he had been lucky enough to have a beta as his vessel. Little did he know he was wrong about said vessel's designation.
Very wrong.
Series
- Part 1 of Deancas stuff
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It is a unique horror, that, despite not being a religious man, Dean truly prays no one else has to experience watching your father beat your brother. God, of course is immovable, or deaf, or doesn’t give a fuck about Dean’s prayers. Not then. Not now
Today is a bad bay. Memories have a habit of boiling up and burning. Dean’s learned to deal with it…kinda.