#dean winchester date

[chxrrylungs]

castiel tried and failed to do something romantic

[paunchsalazar]

Bert and Ernie

[flow33didontsmoke]

You’re dating early seasons Dean Winchester.

divider: @cafekitsune

reblogs are appreciated, asks open

[allthosepeopleilovetofangirlover]

DATING DEAN WINCHESTER HEADCANONS

Dean is the guy who'd pretend that he's the best in the entire universe, but he'll get nervous if he ever sees someone slightly more attractive than him.

He loves to watch movies with you, even more so if they're of his choice. Cuddling on the couch in the Bunker and watching a movie is his favourite evening activity, and he's constantly looking at your face throughout the movie to see if you like it or not.

Dean doesn't want you to accompany him on hunts, especially if the creature you have to hunt happens to be particularly dangerous, like a vampire or a werewolf.

He'll never try to control you, but he will get insanely protective of you and you have had many arguments based on that.

Arguments that almost always get resolved by angry sex or intense makeout sessions.

But for the ones that don't, you two eventually find your way back to each other.

He'll never admit it, but he loves it when you treat him with affection and give him flowers.

If it wasn't obvious, Dean is touch-starved, and you figure it out very soon into your relationship. You make sure to give him reassuring touches ever so often, especially in the times of stress.

Dean is very grateful for those touches, and keeps reciprocating the gesture, but in a much wilder way.

He is very possessive, and will glare daggers at anyone who stares at you for too long. Men who know him know how dangerous he is, and how well he can fight, so they stay away from you. But the strangers who try to look at you in any way other than respect, Dean will not hesitate to throw punches.

For all his playboy ways, he's extremely loyal to you. Will not even look at any other girl when you're in the picture. You're the only one he wants and needs.

Dean likes to pull pranks on you. They're harmless, obviously. He loves to see that adorable expression on your face when you don't know what's wrong when you're being pranked. Once you realise it however, it doesn't take a lot of time for that expression to go from adorable to angry.

You love to pull pranks on him as well, often teaming up with Sam to teach his older brother a lesson. Sam loves it, and though Dean pretends to be angry and offended, he's laughing on the inside.

Frequent rides in the Impala, especially when it's drizzling and a cool breeze is blowing. He just likes to go on long drives with you, no distance is too long with you by his side.

Dean tells you stories of his childhood, yes, even the bad ones. The good ones to get a good laugh while the bad ones for you to get more acquainted with his reality, to know who he really is.

He had taken a lot, and I mean a LOT of time to open up emotionally, it was extremely difficult for him to not be guarded at all times. But nothing is too difficult when it comes to you.

Now, he opens up to you and talks to you about how he feels, instead of hiding his real emotions behind corny jokes and sarcasm.

Whenever you get mad at him, he immediately gets to know and tries his best to make sure that you aren't mad, the process including more corny jokes but you learned to love them anyway.

Sam loves the way you have a positive effect on his brother, how you calm him down from both anger and stress, how you make him less reckless and more affectionate.

The most important thing however, is the fact that you make him less self-destructive. He takes a lot of care of you, but along with you, he has started to learn how to cherish and love himself as well.

You bring out the best in him, and he brings out the best in you.

You're his yin, and he's your yang. Both of you wouldn't have it any other way.

[5sospenguinqueen]

Y/N: Whenever Dean is about to use the shower after me, I turn the temperature to scalding.

Sam: Why-why would you do that?

Y/N: To make him think I am capable of withstanding that pain. I take normal showers, but I want Dean to be a little scared of me.

Sam: (sighs) You’re both idiots.

Charlie: (in awe) That’s genius.

[spookyysinsanity]

dean winchester x fem!reader dating head canons -nsfw edition

not my gif!!^^

18+ only!!! minors dni!!!!!!!

loves fucking in front of mirrors. he likes to be behind you, holding u up by ur hair or neck and he can see your reflection.

goes craazzzyyyy when you moan his name

likes to pretty much fuck you stupid. like to the point ur shaking, can't walk, only can think of his dick and babbling his name

loves leaving marks on your body. like hickeys EVERYWHERE, on ur neck, chest, thighs, stomach, all of it.

likes it when you have lipstick on and kiss his neck

ONLY if you're ok with it, he loves to choke you. especially if you ask.

has a huge thing where he loves to pleasure you first

eats pussy like a man STARVED

especially if ur on his face he fucks that shit up

he's sososo good with his hands. like goooood. it doesn't matter where they are, in between ur legs, on your boobs, your face, neck, hair, whatever bro wherever he is he's doing a damn good job.

loves to send u dirty texts if you're doing research with him and sam. lovesss to watch you get all hot and bothered

loves to tease and play with you in baby. traffics bad? his hands r down your pants. or it's the other way around and you're sucking his dick

jus loves to fuck in(or on) baby idk bro

loves to come up behind you and press himself against you and start jus groping your ass or tits

also will come up behind you and kiss your neck/jaw and his hands will gently come up under ur shirt and trace your stomach and waist

a/n: ok that's all for now! please like and reblog if you liked it, let me know if u want more!

[wraithlafitte]

something i love about supernatural is that you can't immediately tell what season an image is from based on dean but you CAN tell based on what hairstyle iteration sam is on

[wigglebox]

Destiel Pride - Day 2; Love in his eyes

[inlovewhithafairytale]

POV: Dating this emotionally unstable man and being his comfort. or Dating Dean winchester

[strawlessandbraless]

I think about the burger date in 10x09 The Things We Left Behind an unhealthy amount. But then I go watch it and am reminded that Dean gets spooked by the intimacy, experiences bi panic, overcorrects and asks Cas to kill him. The date was going great babe, you didn’t need to do that

[valeron99]

Love their (not)dates <3

[paunchsalazar]

Dean and Castiel in season 14

[szlez]

Burger Date

I decided to try different brushes and I'm not entirely happy with the result. But maybe someone will like it anyway.

And this is what should happen after the date:

Blue, Amber, Aqua, Honey, Purple, Rose, Red, Pink.

Taglist

Pls DM me if you want to be added to tag list or removed from it.

@aniona29, @cosmiccowboycass, @denimshortsdean, @dotti55, @famouskidangel, @markofcastiel , @malicmalic , @meeshsen , @shipsawayandusuallygay, @squirrelsarecool, @strawlessandbraless , @writteninthestarsinyoureyes .

[allthosepeopleilovetofangirlover]

DATING SAM WINCHESTER HEADCANONS

Sam is a complete gentleman. Once you capture his attention, it will be completely fixed on you and he will never even look around at any woman other than you.

That being said, getting his attention is very difficult. He was polite and kind to everyone, so you thought that he didn't want you particularly.

But he did. He liked you more than anyone else, and soon, asked you out.

Sam is the sweetest boyfriend, he'll try his best to know what you like and don't like so that he can make sure that he never makes you uncomfortable.

Hugs and cuddles. He loves it when you keep your head on his shoulder while he's doing research or reading a book. He pretends like he doesn't need affection but deep down, you know he does.

Everyone around Sam treats him like he's a baby, so in the beginning, when you had done that too, Sam had got angry. Very angry.

But as time passed, you saw how talented and capable Sam is, and learned to not underestimate him. Sam fell a bit more in love with you because of that.

Sam is constantly worried about others, including Dean and Bobby, looking at him like he was a freak, like he was inhuman. But you never looked at him like that. For you, he was just Sam. Your Sam.

He takes great pride in the fact that he's tall, and teases you about your height more often than not. You try to tease him back and it eventually ends up in a makeout session.

Sam treats you with great care, but he doesn't underestimate you. He loves and cherishes you while being aware of how strong you are.

He will always make sure that you get enough rest and food. If you're ever upset, he'll try to talk to you and coax the problem out of you. In the sweetest, gentlest way possible.

Whenever he and Dean argue, he always comes to you and talks to you about how he disagrees with most of his family values, and you listen to him patiently, just glad that he doesn't shut himself off like his brother and actually talks about his feelings.

Sam's love language is words of affirmation. He needs to be told how good and kind he is, relying on healthy communication more than anything else. In return, he constantly praises you, showering you with love and appreciation.

Contrary to what most people might believe, Sam is not a boring person. He has different ideas of fun, and though he's not the most joyous or exuberant person around, he's fun to be with. He will make sure that you never get bored in his presence.

That being said, he does get insecure that you might leave him for someone better, someone louder, more enthusiastic, but you convince him with both words and actions that he's the one for you, and you wouldn't even think of leaving him.

He's not the only one who gets insecure, though. Being extraordinarily handsome and cute, many girls and even a couple of guys flirt with him on multiple occasions, even when you're right beside him.

But Sam makes sure to let the world know that he's yours. Many times, to get the point across, he'll kiss you in front of the lot to let them know that you're together.

Sam wants to quit hunting and start a family with you, a quiet, white-fence life, and since it's with him, so do you.

You and Sam are endgame, and both of you are going to make sure that you two stay with each other, forever.

[lacydollette]

ᝰ.ᐟ BF DEAN WINCHESTER ⸻ head canons

notes just dean being a lil softie, whole lotta fluff, sfw, definitely gonna be making a nsfw version for this as well though,, cause I know y’all are freaky like that!

ʚ he def knew u had a crush on him long before you two even dated, so he would flirt with random girls to get u jealous cause he thinks it's attractive

ʚ scared to open up to u at first, too anxious that he’d scare u away with all of the things he’s carrying inside of him, but u always reassure dean that you would never leave him

ʚ 100% acts like a big baby, when you two are alone in the motel room, since he wants to feel ur warmth and affection

ʚ always calls u “sweetheart" even in the middle of an argument.. it’s his way of showing affection.. in some way.. and he can't help it

ʚ he is incredibly protective of u, he would always try to shield u from the worst of it, even if it means being a little overbearing at times..

ʚ he loves flirting with u, even after you've been together for a long time.. he would out cheesy one-liners or make playful comments, trying to make u laugh

ʚ if u ever get hurt, emotionally or physically, it would break him.. he has a hard time coping with seeing u in pain, and he’d go to great lengths to make things right

ʚ the type to just grab u and drive off in the impala, no real destination in mind, just enjoying each other's company and the open road

ʚ lets you pick out the music whenever he's driving.. “Excellent song choice, sweetheart."

ʚ he loves listening to u babbling, even if it’s about the most boring things.. he’d just be happy to hear ur sweet voice

ʚ he’d feel so proud while seeing u flipping off random guys that are trying to hit on u

ʚ he is addicted to ur lips, sneaking in little kisses here and there, sometimes even having a hard time stopping, he just loves u so much

ʚ always has his hands on u someway, especially when he is driving, his palm would be on ur thigh ALL the time

something a lil different today !!

feedback and requests are greatly appreciated !!

tags 🏷️ @gibson-g1rl @beausling @nuemanfilms @angelicjackles @sammyluvr @rubyvhs @nxptvn @seasons-of-death @deansenvy @drewsarms @starkeysprincess