#deanbenny headcanon

[bennylafittelove]

I like to think that Dean kept one of Benny’s jackets after he sent him to Purgatory and would hold it tightly when he’d sleep.

[angelsdean]

pt one here

listen. i flip flop on deanbenny all the time and can entertain multiple conflicting headcanons but. dean was SO hyperfocused on finding cas. do i think there was clear homoerotic subtext and attraction? yea. do i think they were really anything beyond

[hollywoodbabylondean]

Benny for the character ask <33

give me a character

favorite thing about them -how he cares about other people and his general good will least favorite thing about them - that the writers were cowards and homophobic and killed him off favorite line - cant think of any rn sorry brOTP - HEAR ME OUT i think him and garth would've been besties OTP - deanbenny baybee nOTP - sam. again for homophobia reasons. random headcanon - he and his great granddaughter reconciled before he left unpopular opinion - just. straight up cowardice that he was dead in purgatory in s15. song i associate with them - bad moon rising by creedence favorite picture of them

sunglasses benny my beloved

[scoobydoodean]

Hi bestie I just wanted to pop in and say I love seeing you on my dash, you’re so big brained and overall just an amazing person to be around . My fellow Benny girl in arms ❤️🙏🏾

Anessa!!! I was just on my way to ur blog to see if u had anon on to also send you an anon love message <33333 I was going to tell you it is a delight every time you grace me with your presence and no one deserves your deanbenny takes or what you do for benny in general and making sure people appreciate him as they should and you have the most amazing and unique art style it is so lovely and I love how much you think about benny headcanons indeed Benny fans UNITE!!!

[computersucker]

I’m shootin Dean Winchester right back at ya for the character asks because I want to know your Thoughts 😂💚

heehoo okay here goes

favorite thing about them: hes so silly goofy with his little cassette tapes and pajama pants and pie and cowboy fetish. he contains multitudes of Goof

least favorite thing about them: babygirl you have anger issues :(

favorite line: "driver picks the music, shotgun shuts his cakehole" but i'm legally obligated to say so bc i have a sticker of this in my car

brOTP: besides charlie, which i agree, he and ronald from Nightshifter would have been BESTIES if he had lived.

OTP: going to be controversial yet brave and say deanbenny was It

nOTP: w* 🤢

random headcanon: this bitch would probably enjoy a bathbomb

unpopular opinion: i hate when people headcanon that he would have a cat. that man wouldn't have a cat. sorry but he is not that type of girl.

song i associate with them: basically every time i listen to led zeppelin or metallica im like hehe. dean music

favorite picture of them: aww look he thinks hes a real cowboy 🥺

[beauarlen]

Because you’re such a good noodle when it comes to my ranting, I’m gonna give you my idea of what Dean’s heaven looks like because all of the posts I’ve seen talking about it are Destiel centered and I’m a salty DeanBenny shipper❤️ (This is of course a headcannon, but it makes me happy.)

Benny bakes Dean all the pie he wants in heaven. They’re no rules when it comes to your diet up there, so Dean is constantly asking Benny to bake for him because he hardly had the time to actually sit down and enjoy eating without worrying about whatever was going on at the time.

Benny doesn’t mind though, because he likes seeing Dean happy.

Of course since Sam is also up there with Dean and he visits him a lot, Benny always saves a pie or something for him.

Here’s a drawing I did as well:

ahhh thank you so much Anessa !! AND OMG I LOVE YOUR HEADCANON AND DRAWING SO MUCH YOU'RE SO TALENTED <33

i can see benny prioritizing dean's happiness because he's such a good loyal friend to him and not just that, benny in fact was one of the best things that ever happened to dean i will never not say that. i really love the idea of benny baking for dean i just think it's very adorable :(( we really deserved to see a deanbenny heaven reunion too because he was one of the VERY few characters on the show who deserved to be in dean's heaven.

"he likes seeing dean happy" had me so emotional because that's so canon too. seeing dean smiling and having a blast while eating those pies that he baked :(( dean's happiness means a lot to benny. i keep thinking if benny survived he would stand up for dean through everything. we've really been officially robbed of the deanbenny's epic dynamic :// (i would also like to add that benny is obviously supportive but he's also an intelligent and independent dude he's not just "dean's buddy" because if dean actually did something wrong he would call him out on it and he would do that because he really loves and cares for dean.)

benny saving a part for sam is absolutely amazing because it reminds me of how benny sacrificed himself to save him. benny literally recognizes sam's importance to dean and i personally find that very admirable. he's truly been a great friend to dean. sam would've been beyond appreciative of benny if he survived a little longer knowing how benny is truly a nice and caring dude.

i really enjoyed reading your headcanon it made me happy too !! it's a joy seeing people around here who are interested in deanbenny:) it's literally the best dean ship and seriously one of the greatest dean relationships on the show.

side note: i just think it's hilarious how those people centered dean's heaven around d*stiel because in that last virtual panel that jensen did with jared. he was asked what would dean do in heaven, jensen answered that dean would hang out with his brother, his parents and jack. not even a single cas mention *giggles*

[spn-season-16-chronicles]

As today marks two month anniversary of "Y yo a tí, Cas" a friendly reminder that supernatural is just elaborate bible-fairytale fanfiction made into a series.

So in a way every headcanon and fanfiction is as valid as spn itself. Yeah, every and each of them. You have to choose what do you take as a canon and what do you leave out.

Have fun!

[supernatural-jaeger]

Pieces of purgatory part 2 Benny

Pieces of purgatory part 1 Dean

This is for @spnprideweek 🏳️‍🌈 day two: mlm. Benny gains a piece of his humanity back when the human soul train named Dean Winchester lands in Purgatory. This hotheaded, stubborn man that cares so much. How can Benny not give him his heart?

Pls let me know if anyone wants to be added❣️

Tag list: @you-cant-spell-subtext-without @sunfaith

[kbsd]

i am loving this bennaissance truly it’s what benny deserves

[humanoidmoth]

So I headcanon that when monsters die in purgatory they go to the Empty (they have to go somewhere right?). But then this made me think, if Dean goes to the Empty ("you made it loud" now everyone is awake) to rescue Cas, could he also bring back his ex-boyfriend Benny? Yeah, it might make his romantic reunion with Cas a little awkward, but let's be honest, everything they do is awkward. If everyone is walking around in there he'd probably run into him (and his other boyfriend, Crowley), and you cannot convince me that after knowing that Benny was in there that he wouldn't do everything he could to bring him back too.

[winchesternova-k]

EVERYONE ON TWT IS SCREAMING THAT ITS CANON THAT CAS AWAYS THOUGHT DEAN WAS BI AND THAT DEANBENNY IS NOW CANON TOO??? WHAT THE FUCK HAPPENED???

[mybrainproblems]

hm hm HMMM all of this deanbenny posting has me seriously considering writing the deanbenny "prequel" part of the destiel fic I've been outlining bc honestly that's the bit that is more interesting/straightforward to me and then maybe write the destiel half as a separate sequel if I'm up to it?? (Which also avoids the shitty thing where fic end up in a ship tag when it isn't endgame.) Because honestly. The deanbenny part is what I truly love. Diner dishwasher part-time hunter pre-s1 Dean and Benny as the vamp short order cook who he becomes friends with and neither of them know about the other for a while. Mary still died, John still becomes a shitty dad and hunter but there's no Azazel/fate crap.

Also please go check out @postcyberpunkpirate 's college AU comic where Dean and Benny are friends with (blood) benefits and inspired this bc it's hilarious.

[heavenssexiestangel]

What's your favourite DeanBenny headcanon? ^_^

Aaaargh

Hiii! I have so many....

Dean and Benny fell in love in Purgatory. They often talked about getting out and being together, probably always on the road, even though Dean would always remain human. They thought they would be able to start something new. Together.

[good-things-do-happen-dean]

.

[gooferdusted]

If u want more deanbenny or sastiel thoughts, I would love to hear your thoughts on them all being on a horribly awkward double date. Sam and Dean planned their outings and didn’t intend a double date, but they ended up in the same place after telling the other they had a hot date (but not saying with who) and saw each other. They then felt a weird obligation to sit together and act like it’s not weird and not address the fact that they were dating their best friends. They’re awkward babies

GOD this is so funny I'm crying

they go to a mildly fancy restaurant

bc sam and cas were like "we should go on an actual date and not just stay in our room and half pay attention to holiday baking championship while we drink tea and talk about philosophical shit"

(that's how all their "dates" go, sometimes they take picnics or get milkshakes, but that's generally how things are)

(or they just read together in the same room)

and dean and benny are like "we should go on an actual date and not just get fucked up at the bar and sing an embarassing amount of karaoke"

so they ALL manage to book the same restaurant on the same night, somehow

Dean's wearing his Formal Flannel and Benny's wearing his Formal Leather Jacket

and it goes super well for a while, even is dean and benny cant stop giggling bc this is so DUMB, they're not on some first tinder date, theyve been together for YEARS and this is just the dumbest shit but the candlelight is really nice

dean eats like an Entire lobster in the grossest way possible and Benny's just like 😊💖😊💖😊💖

sam and cas are also giggly and dumb

they get one of those to split sundaes w the two spoons

they're so sappy and lovey w eachother, its gross

and then sam and dean spot eachother from across the room and it's like this:

[quality-octopi]

Can people please share some of your head cannons for me to draw? I'll try my best but they'll probly be simple sketches because this is just for fun.