Top 5 Dean relationships (including platonic/familial) <3

ok i'm going completely platonic/familial with this one bc the casgirl in me gets a little jelly if i think abt his other romantic relationships TOO much like they're good great even ! but. cas...djfkdk ok anyways

dean + jo - been thinking abt them A LOT lately ever since my mutual gender envy post and just. yeah they're gender buddies<3 they have a weird dynamic that they don't really understand for a long long time (both thinking they have crushes on each other but then thinking no that's weird and not right but still not able to fully understand what they're feeling) and then once they doo get it they just chill together like sleepover hangouts where they get high and talk abt their gender + sexuality feels and jo's like "i love boobs" and dean's like "god i wish i had tits" and jo's like "you dooo ur tits are great !" and then they just giggle and jo paints deans nails and dean buzzes jo's head<3

dean + bobby - THAT'S HIS DAD !!!!! HIS REAL DAD !!! like bobby is so important "you're the closest thing i have to a father" yeah! bobby's not perfect and he's also Not Great at talking abt things but he's /there/. he's always been there and he's defended dean against john and looked out for him and tried to give him some snapshots of a normal childhood, taking him to the park to play catch instead of shooting guns. that scene where bobby holds dean's face and cries…KILL ME.

dean + jack - DEAN IS A GOOD PARENT the hill i will die on. dean got a lot of things wrong with jack, yes. the guilt eats him alive 24/7. a lot of it was chuck's fault. a lot of it was the ghost of john winchester. a lot of it was just grief and displaced anger. it doesn't /excuse/ his actions but !!!! if he could do it over, if he could do it different, if cas hadn't died i just Know he'd be moving in to play house with cas and take care of that kid, the devil's son or not. so like, i just know that /after/ in the soft epilogue they all get, dean would put the work in to fix his relationship with jack and conciously do everything he can to Not Be John. That's his parenting motto: Don't Be John.

dean + charlie - his bff that he ISN'T in love with (unlike with cas). he gets to be his mega nerdy self with charlie and he doesn't have to worry about /feelings/ or anything. they go on little shopping sprees, have little fashion shows (we all know dean Loves to be put in little outfits), they watch nerd movies and gossip and talk abt their big gay feels. he needs that !! he's never had that before !! she's also the little sister he never knew he wanted and with charlie, for once, he gets to JUST be a brother. they have the sort of sibling bond he never really got to have with sam bc he was always also being a parent, thus making himself fundementally unknowable to sam. like s1 sam? literally does not know a thing abt dean it's crazy. anyways.

dean + mary - HELLO INSANE BRAINWORMS. they are mirrors. they hate each other. they love each other. they can't stand seeing the reflection of themselves in the other. dean also holds onto every similarity with a vicelike grip. his lips are mary his eyes are mary his hair (blonde dean truthing!) he looks in the mirror his whole life and sees her even as he's trying to twist and mold himself into his father. he never can because sam is john's true mirror. he never can because he is alway always going to be his mother's son. and mary, god mary can't look at him because she never wanted this for him. she can't look at him because where is her baby? she can't look at him because all she sees is herself, the hunter, the killer, the woman who could never quite mold herself into a mother. except. well. dean DID do that, and did it better than she ever could. and she resents him for that a little bit, and resents him for putting her on that pedestal, and resents him for asking her to BE a mother. but she also deeply mourns the fact that dean had to take her place, that dean lost so much of his life, his childhood, trying to fill the empty space she left behind. i could go on forever abt this.

ok this reply got SO long but. yeah<3