#charlie (polycule status: *might* dick dean down in some kind of bodyswap situation but only so they'd both get bragging rights)

[shinelikethunder]

let's also give a "he would not be That flavor of fucked-up, his flavor is way more convoluted and specific" shoutout to Sam Winchester, the one who does regularly get all pissy and judgemental about Dean's one-night stands, his slutty hedonistic creature comforts, the women he hooks up with, the men he bonds with, etc... and very earnestly frames it as concern for Dean's well-being and worry that Dean is throwing himself away on undeserving trash. no matter whether they both know full well that Dean will be on his merry way the next morning or whether Sam's seething resentment of a perceived threat to his primacy in Dean's life can be seen from space. only ONE category of Dean's relationships is allowed to be worth anything, thankyouverymuch, and whatever was going on with Dad was on thin fucking ice. keep on being hilarious and full of disorders, kings

i don't actually think teenage Dean Winchester would be spurned-lover-style jealous of teenage Sam's girlfriends i think based on his s1 behavior that it's far more likely he went "HELL YEAH my little brother is DATING he is going to SLAY at this and i'll make sure of it," unilaterally appointed himself Sam's wingman, had to be beaten back with a stick from micromanaging his brother's love life, and probably lovingly fantasized about all the hot chicks Sam was gonna hook up with and all the things they'd get up to because let's face it, who wouldn't fall head over heels for the guy? (speculation about kissing practice, which of course Would Not Count as anything except making sure the little nerd did their family proud, is left as an exercise to readers who are so inclined.)

also probably the closest thing to a jealous shitfit he pulled involved one (1) time Sam ditched a hunt to be there for his then-girlfriend's Important Life Event, and it'd be like 40% loudly-expressed "he should be putting his FAMILY first" and 60% ferociously-suppressed "we don't get to just DO that! if i've accepted only ever being able to date super casually for a few weeks at a time before we blow town then where the fuck does he get off thinking he can just PRIORITIZE this COMMITTED RELATIONSHIP BEHAVIOR bullshit. that i tooootally don't want or care about anyway. because it's for SISSY NORMIE LOSERS, not a tight-knit clan of ULTRA-COOL SECRET MONSTER HUNTERS like us"

like i think Dean did accept much more readily, long before he could even realize the ramifications of what he was accepting, that the way they lived meant the Winchesters' only long-term relationship option was "rampant emotional incest that we don't have to acknowledge as long as we all only bang girls," but he also canonically had all kinds of festering resentment about missing out, and was aware on some level that their lives required the sacrifice of a lot of things he secretly longed for (and made a lot of noise about devaluing in favor of What's More Important)

and the toxic cocktail of that + envy of Sam's ability to just go "nah fuck expectations i want something else" + boundary-challenged investment/enabling/policing of each other's heterosexual exploits as a bulwark between their family dynamics and The Unspeakable + freakout over the early warning signs of a difference in values on family loyalty + inchoate terror of losing him to the outside world one day + unthinking idolization and projection along the lines of "well of course this girlfriend would take him away from us and wrap her entire life around his if she could, i mean, have you met him? who wouldn't want that? this is WHY we have to keep it casual and not get girls' expectations up"...

...the entire dynamic of Dean being Sam's number one hookup cheerleader but also perceiving signs of romance/commitment as a threat... s1 Dean trying to have a hand in pushing him towards actual romantic prospects anyway, because he's worried about Sam grief-spiraling and has reluctantly accepted that the rupture in the family is about things Sam genuinely wants, even as Sam's grief is already driving him to the conclusion that they aren't worth the cost and meanwhile the brothers have spent all season bonding even closer and more claustrophobically as adults...

well, i think all that is way more interesting, and in many ways even more fucked-up, than applying bog-standard jealous boyfriend tropes to the absolute mess of their upbringing

[thepastisaroadmap]

#cas crash-lands into the 'family' slot mid-apocalypse but is not exempt from being on thin fucking ice when sam feels extra-rejected #it's cool though it's fine once they've bonded over almost ending the world through good intentions and also x-treme metaphysical kink play #(hello have i told you the good news lately about being delivered from the vale of tears and ship wars by the wincestiel agenda) #spn: because sometimes a family can be both a paramilitary cult AND a polycule #other relationships slotted under 'family' include bobby (polycule status: sam doesn't wanna think about it) #charlie (polycule status: *might* dick dean down in some kind of bodyswap situation but only so they'd both get bragging rights) #mary (polycule status: sam's staying out of their beef over who gets to be john's widow but is jealous they get to have it) #and jack (polycule status: 'turtles‚ ninja or otherwise‚ do not fuck' copypasta harmonizing with multiple frequencies of trauma screaming) #lisa's a whole other situation that one was more like 'for the love of god please retire and go join that woman's family after i'm gone' (tags via @shinelikethunder)

i don't actually think teenage Dean Winchester would be spurned-lover-style jealous of teenage Sam's girlfriends i think based on his s1 behavior that it's far more likely he went "HELL YEAH my little brother is DATING he is going to SLAY at this and i'll make sure of it," unilaterally appointed himself Sam's wingman, had to be beaten back with a stick from micromanaging his brother's love life, and probably lovingly fantasized about all the hot chicks Sam was gonna hook up with and all the things they'd get up to because let's face it, who wouldn't fall head over heels for the guy? (speculation about kissing practice, which of course Would Not Count as anything except making sure the little nerd did their family proud, is left as an exercise to readers who are so inclined.)

also probably the closest thing to a jealous shitfit he pulled involved one (1) time Sam ditched a hunt to be there for his then-girlfriend's Important Life Event, and it'd be like 40% loudly-expressed "he should be putting his FAMILY first" and 60% ferociously-suppressed "we don't get to just DO that! if i've accepted only ever being able to date super casually for a few weeks at a time before we blow town then where the fuck does he get off thinking he can just PRIORITIZE this COMMITTED RELATIONSHIP BEHAVIOR bullshit. that i tooootally don't want or care about anyway. because it's for SISSY NORMIE LOSERS, not a tight-knit clan of ULTRA-COOL SECRET MONSTER HUNTERS like us"

like i think Dean did accept much more readily, long before he could even realize the ramifications of what he was accepting, that the way they lived meant the Winchesters' only long-term relationship option was "rampant emotional incest that we don't have to acknowledge as long as we all only bang girls," but he also canonically had all kinds of festering resentment about missing out, and was aware on some level that their lives required the sacrifice of a lot of things he secretly longed for (and made a lot of noise about devaluing in favor of What's More Important)

and the toxic cocktail of that + envy of Sam's ability to just go "nah fuck expectations i want something else" + boundary-challenged investment/enabling/policing of each other's heterosexual exploits as a bulwark between their family dynamics and The Unspeakable + freakout over the early warning signs of a difference in values on family loyalty + inchoate terror of losing him to the outside world one day + unthinking idolization and projection along the lines of "well of course this girlfriend would take him away from us and wrap her entire life around his if she could, i mean, have you met him? who wouldn't want that? this is WHY we have to keep it casual and not get girls' expectations up"...

...the entire dynamic of Dean being Sam's number one hookup cheerleader but also perceiving signs of romance/commitment as a threat... s1 Dean trying to have a hand in pushing him towards actual romantic prospects anyway, because he's worried about Sam grief-spiraling and has reluctantly accepted that the rupture in the family is about things Sam genuinely wants, even as Sam's grief is already driving him to the conclusion that they aren't worth the cost and meanwhile the brothers have spent all season bonding even closer and more claustrophobically as adults...

well, i think all that is way more interesting, and in many ways even more fucked-up, than applying bog-standard jealous boyfriend tropes to the absolute mess of their upbringing