dean winchester headcanon

Dating Dean Winchester Would Involve...

Originally posted by deangifsdaily

Dating Dean Winchester would include…

- Stealing his shirts 24/7. You usually wake up before him and when you do you steal one of his shirts. Resulting in him putting his arms around you as you make breakfast and whisper how much better you look in his clothes.

- Singing loudly together in the Impala. And if Sam’s in the car with you he pretends to be annoyed but he secretly loves seeing the two of you so happy. He joins in eventually.

- You always have each other’s backs during hunts. If one of you got hurt, you make sure to stick each other up and press a small kiss on the wound.

- Although he doesn’t seem like it, Dean was really gentle with you the first time you had sex. He would ask if you were okay every five seconds and make sure that you enjoyed it as much as you could.

- After sex cuddles.

- Post mission cuddles.

- Morning cuddles.

- Just so much cuddling, he’s a huge cuddle bear.

- You and Sam quickly becoming best friends. So much so that you sometimes spend more time with him that with Dean. This results in angry, jealous sex.

- He trusts you just as much as he trusts Sam—if not more—and he always opens up to you about everything and vise versa.

- Dean always uses old pickup lines on you when you’re upset. Then he’d pull you into his arms and tickle you senseless. After a while he’ll just hold you in his arms as you tell him all about what’s upsetting you.

- Always being able to make each other smile

Being Dean's best female friend

Originally posted by superuunatural

  • lots of inside jokes
  • always having someone to pick you up after a date gone wrong
  • sending each other stupid messages
  • it taking  Dean a long time to completely open up to you, but once he does you are the only one he tells his fears and insecurities
  • road trips
  • whenever one of you has a bad day a single message is enough and the other comes over with a bottle of whiskey
  • being able to rant about your problems while Dean just listens
  • finishing each other’s sentences
  • saying the same thing at the same time
  • being able to read Dean like an open book and he is able to do the same
  • Dean offering to beat up your ex
  • calling Dean in the middle of the night just to tell him something funny you thought of
  • staying alone at the bunker while waiting for Dean to come back from a hunter
  • Dean hanging out at your home, waiting for you to show up while emptying your fridge
  • Hanging out for hours saying absolutely nothing
  • Dean hating all of your boy(girl)friends, claiming they aren’t good enough for you
  • cuddling while watching movies
  • Dean is the best platonic cuddler and his hugs always make you feel better
  • resting your feet on his lap while eating takeout
  • Dean helping you pick out clothes for a date
  • talking about your worst sex experiences
  • Dean once tried to help you paint your nails when you broke your arm
  • Dean ruffling your hair
  • Dean never judging you 
  • forehead kisses 
  • being one of the few people Dean trusts
  • Dean giving your new boy(girl)friend the protective big brother/best friend speech
  • insisting the boys celebrate holidays like Christmas and Halloween
  • spending every holiday at the bunker and decorating everything – really, you go all out because you know the boys deserve something as close to a normal holiday experience as possible
  • sharing bad jokes
  • being Dean’s wing woman
  • Dean never letting you down when you need him
  • not seeing each other for a long time when Dean and Sam are on hunts far away, but as soon as he’s back it’s like he never left
  • Dean knowing that you are one of his weaknesses so he insists on you having a gun and an anti-possession tattoo
  • making Dean a photo album for his birthday to remember all the good times you had
  • jam sessions in the car
  • seeing each other naked and not being shy about it
  • Dean building up your self-confidence when you feel self-conscious
  • Dean calling you his best girl
  • a lot of people thinking you are dating
  • Dean wrapping his arm around your shoulders
  • Dean calling you after a bad hunt
  • sitting somewhere outside and drinking beer while telling each other your dreams
  • long discussions about the silliest things – like if you could only eat one food for the rest of your life, what would you choose or if aliens exist
  • Dean being protective of you and you being protective of him
  • Dean buying you comfort food and watching rom-coms with you after a breakup
  • sleeping in the same bed and cuddling because it feels nice to wake up next to someone

Bisexual!Dean never coming out to John because he knew his father would never validate his sexuality or approve it. (;_・)

Learning how to be comfortable with his bisexuality and wearing it like a badge of pride. (*•̀ᴗ•́*)و ̑̑

Having one-night stands/dates/etc. with men and women, but acknowledging his attraction to people of nonbinary genders, because Dean soon understands that bisexual doesn’t mean attraction to just men and women. \(^▽^@)ノ

Bisexual!Dean going to a pride parade while holding a bisexual pride flag and almost crying because he’s welcomed and accepted here. But Dean does get angry when he learns how much bisexuality is an invisible sexuality in society, even in LGBT+ spaces. ୧| ͡ᵔ ﹏ ͡ᵔ |୨

Making jokes about his bisexuality and Sam groaning because the puns are so bad. ╰(✿´⌣`✿)╯♡

~Bisexual!Dean~ (>^_^)><(^o^<)

I have this really sad headcanon about Dean when he was a teenager where every time John came home he’d be drunk off his head and he’d shout at Dean and maybe sometimes hit him but, Dean would always try and hide it from his brother. When he was sure Sam was asleep at night he used to cry in bed, just cry and cry. Sometimes Sam would wake up and ask him what was wrong and Dean wouldn’t say anything and Sam would say “it’s dad, isn’t it” and silently hug him while he cried 


Word Count:1,174
Summary: Dean has his own little secret routine, one that Sammy doesn’t know about, and he’d like to keep it that way. It doesn’t matter what time of the day or night it is, Dean has to get in his car and travel the distance to make sure his ritual is done right. 
Warnings: Feels? Idk.

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anonymous asked:

Top five headcnons for Dean? :)


  1. When Dean was a demon, Crowley tried to assign him a Hellhound, saying that he could use it and “it’s not a damn dog, Dean, it’s a fucking Hellhound, how can you refuse it?”, but then doesn’t even listen to him. He may have been a demon back then, but he hated those damn things.
  2. Dean has always taken everything to heart, especially as a kid: he would cry all night because Sam threw a toy at him calling him “idiot” in a stupid little fight, while as a teenager he would laugh every insult off but then think about it for days, wondering what’s wrong with him and if maybe that person secretly hates him (he concludes that they probably do). Sarcasm is a shield that he learnt to use to hide all of this.
  3. The first time Sam went out on a date, Dean followed him, worried that he could get hurt, “stumble across a supernatural thing” (as he told John when his father found out) or simply that the guy (or girl, biromantic!demisexual!Sam is my favourite though) could be rude. He was not gonna let some random dude hurt his lil’ brother (who could kick that guy’s ass, but that’s not the point)
  4. Dean loves it when people touch his hair. If somebody pet him there, the world could end he would be too relaxed to notice.
  5. Once, Dean broke a boy’s arm because he jumped on him from behind. Dean was seventeen years old and reacted out of instict. He didn’t mean to hurt him and felt hella guilty over it.

Okay but Dean not accepting that things are okay between him and Cas after the bunker, and Dean doing everything above and beyond the call of duty to make sure Cas knows that Dean’s sorry and that he would never, ever, ever want to hurt him and never will again

so he texts Cas every night to make sure the ex-angel is still doing okay

so he calls every week about a case he and Sam are working on and invites Cas to come along if he’s free

so he starts reminding Cas that he’s important and that he and Sam miss him (but Dean most of all)

so he asks Cas to move in to the bunker

so he spends all his extra time cleaning because he still feels guilty about the mess and destruction he caused

so he sometimes steals Cas’s trench coat at night when Cas is sleeping so he can wash it for him and Cas can walk around in a coat that smells nice and reminds him of home

so even when Cas is in the bunker Dean still texts him from across the room and asks him if he wants to go out for pizza or a movie

so one day Cas will finally approach Dean and ask him if everything’s okay

so Dean will lie and smile and say everything’s fine

so Cas will look at him with those sad eyes that always makes Dean cave a little and tell the truth

so Dean tells him

it’s still not okay

he’s still sorry

he still wants to apologize even though Cas has forgiven him

and that’s when Cas turns everything around and realizes it’s not just him that’s needed the extra comfort

and that’s how Dean and Cas finally begin to take care of each other

so both of them can always remember that even if it’s not okay right now

it will be.

I have this headcanon that is Dean died on the show, Amara would show up out of like NOWHERE and go full wrath of God on whoever, seriously like, “MINE!” before bringing Dean back to life and making sure he’s breathing and his heartbeat is strong.

Meanwhile, Chuck is in the corner facepalming. “Amara, you can’t- I told you- you can’t just intervene in the lives of humans.”

“But this is Dean.”

“Yes, and I’ve brought him back plenty of times, but it finally got to a point I realized I had to stop.”

“Then I will pick up where you left off, but he is my favorite and nothing like that is to happen to him.”

“Well, you better include Cas and Sam in that equation, because that’s how it works. Like, seriously, it’s never ending. They die A LOT. And you’re gonna have to mind wipe them every time so they don’t know we were here. They can’t purposefully get themselves killed knowing we’ll bring them back. It’s easier to just leave him dead, sis, I’m not kidding. It’s a full-time job trying to protect them. You’ve basically adopted problematic puppies, Amara, along with any other puppies they adopt.”

Age 4

Dean Winchester sat on the hood of a Chevy Impala. His father sitting next to him, holding his baby brother. He watched his home go up in flames. He asked where his mother was. They spent the night at a family friend’s house.

Age 6

Dean quickly learned that the musty hotel rooms they stayed in were going to be the closest thing to home. He had seen some books his father checked out from a library. There were stories of ghosts and demons in them, some with frightening illustrations. Dean was teaching Sammy how to talk more. John had taught him how to use a shotgun.

The first time John left for a multiple day hunt, Dean cried himself to sleep. He never thought he’d see his father again, just like his mother.

Age 8

John had told Dean all about the creatures that go bump in the night. He told Dean that it was dangerous, that’s the reason why he learned how to use a gun, that he had to keep Sam safe. Dean told a little girl at the park that he was going to kill monsters. Her mother shuffled her daughter away, reprimanding him. Saying he shouldn’t talk about such dark, creepy stuff. That he’s just scaring people. He learned to keep quiet about his home life.

Age 9

It was the five year anniversary since his mother was murdered. John held a bottle of hard liquor close to him, guzzling it down. This day was always harder than the others. Sam dropped his dinner on the floor, John proceeded to scream.

Age 13

An open beer sat next to where John had passed out on the motel couch. Seeing his father drink so often, he was curious. He took a sip and crinkled his nose. The yeasty flavor hitting his taste buds. He didn’t see the appeal yet.

Age 14

Dean noticed little hairs growing on his chin. He used to sit and watch his father shave with a straight razor. Smothering his face with shaving cream he drug the blade across his cheek. Sam sat on the floor, watching as he did. Sam had to help Dean bandage up his face. When John came home he scolded him to be more careful, but a bit of pride showing through.

Age 16

Dean went on a hunting trip with his dad. He met a girl about his age whose smile alone made his pants a bit tighter. He ended up getting drunk on strawberry wine coolers with her. He later found out that sex was a way to escape his growing depression.

Age 18

While Sam was trying to make friends at school, Dean was busy picking fights and chasing girls. He was growing into his badass facade and attending parties. He kissed a boy during spin the bottle. It was only because he couldn’t back down from a challenge, of course.

Age 21

The first night after Sam left for Stanford, Dean sat in the Impala crying. Scared he would never come back. He chased his tears with a bottle of booze.

so my headcanon is :

Remember this episode when Charlie was attacked by a djinn and she has to tell goodbye to her momma forever well my headcanon is that she came back to see the boys because she was so sad and a little afraid, she went back because she needed the boys company, she needed them to be there for her so they spend a few days together and one night when she was really sad and she couldn’t sleep she asked Dean if she could come and spend a little part of the night with him he agreed of course, he hugged her very tight, they stay like that for a while, she cried a little and finally they felt asleep just like, without any sexual tension or anything just a profound love and affection between to people 

So I just came up with a funny dean and Jess headcanon:

So imagine like the boys don’t know she’s alive and she breaks into the bunker for something, the boys wake up and like grab her or something and when the lights get turned on they’re so stunned, Jess notices Dean’s over sized kiddy smurf slippers and just looks at him 
“I love the smurfs.”

Are you Ready? I’m Ready.

Dean stood there, nerves running through his body. Sam pats his back and pulls out a small flask from his pocket. Dean chuckles, taking the flask from his little brother and taking a sip. The whiskey calms his nerves.

Castiel looks out the window, staring out at the grass. The light shines down on the grass, making the color of the blades lighter. He smiles to himself, because it reminds him of Dean’s eyes. Balthazar walks up to him, laughs softly at his tie. He reaches to fix it, Castiel smiles, quietly thanking him.

Sam watches his brother pace the room, his hands in the pockets of his black slacks. He watches Dean with a smile, because his older brother was finally getting a happy ending.

Balthazar sat in the corner, watching Castiel by the window. He chuckles out loud at the way Castiel’s head tilts to the side, looking every bit anxious. Castiel looks up from the window, a small smile on his face.

Dean wonders if he picked the right color for his suit, he had seen the gray two piece and thought it would be perfect. He slipped the tie through his fingers, it had taken him some time to find the right tie. Feeling relief when he found  the exact color tie that matched Castiel’s eyes.

Castiel slipped his hand in his jacket pocket, making sure it was still here. Looking over at Balthazar, who was busy looking at his phone, Castiel takes out the note. It’s aged, it’s been a few years, but there it was. The note Castiel had found in his trench coat one day, sprawled in Dean’s handwriting, the words said, “ I’m sorry Cas. I need you Cas. I love you, Cas.” Castiel smiles softly, before folding the note up and placing it safety into his pocket.

There was a soft knock on the door, it was time. Sam smiles, looking to his brother, he ask if he’s ready. Dean sighs contently, “I’ve been ready for a long time, Sammy.” The brothers exchange quick hugs, before leaving the room.

Balthazar opens the door, it was time. Castiel moves away from the window, buttoning up his jacket and walking towards Balthazar. “Are you ready, brother?” Castiel smiles, nodding, “I’ve waited a long time for him.”

At the same time, Dean and Castiel both enter the hallway. Their eyes meet and for that split second, the whole world is still. They meet in the middle, Castiel reaches over and touches Dean’s tie. “I like you’re tie.” Dean smirks, touching Castiels arm, “It’s in your pocket, isn’t it?” They knew each other so well, no secrets between them. Castiel nods, reaching down for Dean’s hand. Fingers intwine, the two souls walk down the hall, followed by Sam and Balthazar. They pause when they reach the large brown door, the words Marriage Bureau in white, lingered over the door.Dean looks over at Castiel, the man he fell in love with , all those years ago.Castiel smiles wholeheartedly at Dean, the soul he fell in love with, all those years ago. “Are you ready?” Dean ask, lightly giving Castiel’s hand a squeeze. Castiel smiles at Dean, knowing there was only one answer he was prepared to give, “I’m ready.”