it/its β actually schizophrenic β adult β AO3 and main tumblr are both DrowningInRedInk β not quite as much of a shipper as implied by the fact that wincest is in my url β yes I like wincest and deanjohn and samjohn but I am aro above all
Hello everyone! I'm schizosamwincester. If you want something to call me, I've been going by Satan online for a long time now. I'm 23 and I use it/its pronouns. My main blog is @drowninginredink and DrowningInRedInk is also my ao3. And yeah, as the url implies, I'm schizophrenic.
I write a lot of one shot fanfics, generally pure angst or angsty smut. I send out weekly Wincest Wednesdays asks. I make the occasional webweave. I talk probably way too much about how Dean is aromantic and aplatonic, and really should try estrogen. As you can probably tell from the username, I like using Sam as my self-insert, particularly when it comes to schizophrenia.
Outside of fandom, I'm a nursing aide, I play viola and sing in choir, I play DND and GM Monster of the Week (which is a tttrpg you should really try if you like Supernatural), and I sometimes do theater.
I do ship wincest, as you can tell from the url, but I'm aromantic above all, so I write and talk a lot more about gen stuff than anything. Also I really enjoy deanjohn and samjohn. I make sure to tag all ships, so even if you don't like wincest (or deanjohn or samjohn), this blog should be safe for you if you filter that tag.
My general tagging system is very straightforward descriptions. Characters are tagged #firstname lastname, or #name supernatural if they don't have a last name. Headcanons are all tagged as like, #trans femme Dean Winchester or #schizophrenic Sam Winchester. I am not creative about this, so if you're looking for something, it shouldn't be too hard to find.
Don't be afraid to DM or send asks! Just know I'm extremely talkative, so not only will I reply, it will be multiple paragraphs.
All my webweaves are here. My wincest wednesday manifesto is here. My fics are all below the cut:
Let's see where this ends - Dean/Jess
Fixing all the problems that you made in your own head - schizophrenic!John, no supernatural AU
You sound absurd, even if you're right - schizophrenic!Sam, sampreg, Sam & Dean, past Sam/Lucifer
The Story Doesn't Change - schizophrenic!Sam, Sam & Dean, Mystery Spot
Everything I thought I knew has fallen out of view - schizophrenic!Sam, Sam & Dean, It's a Terrible Life
the only hoax I believe in - Dean/John, Lucifer Rising
Do you ever feel that this should be officially the end? - Pre-Series, John, Murder/Suicide
Pretty Thing (you'll be complete) - Closeted trans woman!Dean/Post-op trans woman!Bela (smut)
Hold your breath, I'll hold mine too - past Sam/Jess, Sam/Dean, sampreg, miscarriage
You can call it loneliness - Bobby/John, Dean/John, Sam/Dean
If She Had Lived - Jess Lives, Depersonalization-Derealization Disorder, Sam/Jess, Jess/OC
Dangerous Questions - Aplatonic Dean, Dean/Cassie
That's just not us - Aplatonic Dean, Sam & Dean
For the best - Aplatonic John, John's breakup with Bobby
Sissy - closeted trans woman!Dean/John (part 1)
Sister - Sam finds out about trans woman!Dean (part 2)
Subsist - Vignettes between Sam and closeted trans woman!Dean (part 3)
Insisted - Bobby finds out about trans woman!Dean (part 4)
Drink to Forget - AU where Sam dies in Carry On instead of Dean
I remember when your head caught flame - Sam/John, underage, first kiss
If He Asked - one-sided destiel, established wincest
You can pin and mount me like a butterfly - dean/john, smut, castration
Like in the movies - aromantic Dean, very underage Dean/John
But they were fucked up in their turn - closeted trans woman!Dean & closeted trans woman!John
Take My Body - trans man!Sam/John
A disfiguring chicken pox of the soul - weirdcest, weecest, trans boy!Sam/trans girl!Dean (not that either knows it yet)
like the baptism he never had - Sam/Dean, necrophilia, piss (All Hell Breaks Loose)
Silver Linings - Sam/Dean, necrophilia, piss (yes, again. But this time it's Mystery Spot)
Like Flies from your Face - Dean & Bobby, suicidal!Dean (All Hell Breaks Loose)
Tonight I give in to the fantasy - Trans woman!Dean, sex worker!Dean
No other box I choose to use - humanfucker!Gabriel (Hammer of the Gods)
Sucker love is heaven sent - Gabriel/Adam smut
Live through this, and you won't look back - trans woman!Sam
I'll use you as a warning sign - Sam/John, Dean/John, unplanned pregnancy
Hobbies - Dean & Bobby (& Sam), Dean's love of hentai
the road is so long - one-sided John/Dean, pining Dean, Christmas
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I think I'll go nice and broad here. It's pride month, so talk about absolutely any LGBTQIA+ headcanon you have for supernatural. How did the Winchester of your choosing discover they were attracted to the same gender? Which side character was definitely stealth trans? Who do you know in your heart was aspec or intersex? And etc. You have free rein to spread whatever gospel you want, whether it explicitly contains any wincest or not, as long as it is queer
-@schizosamwincester
oh man where to start (ignore that im practically a week late)
sam- demisexual 100%, he needs some kind of connection, one night stands are not for him. i like to think hes open to any gender but tends to have a preference for women, but that might just be the urge to be canon-compliant in me. but i AM a sucker for the idea that he played around at stanford, giving and taking up the ass
dean- he dont like labels yk? he wants to believe hes a strong-willed red-blooded american who only fucks women, but i like to think he's not as straight and narrow as he tries to be. i also like the hc that hes aromanitc, but that could be projection
cas- i know that jimmy is a cis male but i like to think cas is bare, like a barbie doll. he walks that line between pansexual and aroace, all or nothing and hes not sure which it is
as for side characters:
kevin is 100% trans, hes such a rat i love him. please, his last name is TRAN, imagine all the jokes he's made
ok the thing I like most about this is all of the nullification talk has been about late seasons Sam, which is when I think he'd really want to not have a dick
if the dick gets taken away earlier and in a highly non-clinical way.... then he has what he wants (no dick) but also deep, gnarly scar tissue and major surgery and urinary problems so he has to think about his dicklessness even more than he'd be stuck thinking about his dick! marvelous!
Samβs family was God knows how many miles away. Dad hadn't said a word to him since he was nineteen. Sam couldn't remember the last time he lit a match, or held a gun, or even looked at a motel. For years, Sam went to the same school every day and slept in the same bed every night. For the first time, Sam's life was completely normal.
It didn't fix a goddamn thing.
When he caught the scent of someone smoking outside, Sam saw his father dropping a half-finished cigarette into a grave. His mind found a supernatural explanation for every news story he heard. In the middle of conversation, Sam swore he saw his friend's eyes flash with black.
On weekends, Sam accepted Bradyβs never-ending invitations to parties, then came home and studied until the words of his textbooks were burned into his retinas, but when he laid down in bed, he was still overcome with the urge to abandon Stanford completely and find something, anything to waste. His fingers itched to feel a trigger beneath them. Despite himself, Sam stole salt packets from the dining hall to line his windows and slept with a silver blade beneath his pillow.
Then he met Jessica.
Jess was like nothing Sam had ever known. Her voice was soft; her eyes were kind; her very skin glowed like the sun lay just under its surface. Sam lost his virginity to rough, calloused handsβJessβ were so smooth that he was surprised she ever even held a pencil. Sam grew up in dimly-lit motel rooms, hiding in shadows and sneaking out in the middle of the night. Jess carried sunshine into every room. Her smile alone contained more warmth than a summer day in Flagstaff.
It wasn't enough.
When Sam woke with another body in his bed, he instantly smelled sweat, motor oil, and musk. If he closed his eyes while Jess was going down on him, he expected to see buzzed hair between his thighs when he opened them. Somehow, the second her small, soft hands grabbed Samβs hips, they grew and became covered in scars and callouses. Sam tried to leave the past behind, but it haunted him regardless. There was no way to salt and burn his own memories.
Jess' presence made no difference. Sam still had to turn off the news whenever he entered a room. He kept salt packets in his pockets. His silver knife was always tucked into his belt.
Lately, when Sam went to sleep, he saw Jess on the ceiling, lit by a ball of flames. Even living in paradise, Sam couldn't help but look for monsters.
Sam loved Jess, but she didn't change a thing. He was still the man that he was raised to be.
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john and dean pre fucking, john tells him "open up" and dean dutifully opens his lips, john slips two fingers inside and feels around, feels around his tongue and teeth and cheeks, soft padding of fingertips feeling their way around dean's mouth, and dean is panting around them, he's achingly hard and has no idea why
What if Sam didn't notice the first time Dean broke into his apartment? What if Dean got in, helped himself to a beer from the fridge, and then just wandered around the living room? Looking at pictures on the walls (in the dark, so he doesn't notice the corner of a picture of him and Sam sticking out of the LSAT study book on the coffee table), looking at the uncluttered, settled, homeyness of this place Sam lives. With a girl. With not Dean.
What if eventually, he gets tired of waiting for Sam's hunter instincts to kick in, because clearly Sam's gotten rusty if he hasn't woken up yet, so he makes his silent (maybe not-so-silent, maybe he's making a bit of noise on purpose because he wantsneedshungers to feel Sam against him like he used to, when they were younger and sparring) way to the bedroom. What if he pauses at the door, open just a crack, because those sounds are muffled but quite clearly involved and Dean's never had a chance to walk in on Sammy with a girl before. Walk in on Sammy naked, sure, that was inevitable with how they grew up. Walk in on Sammy jerkin' it, yeah. That was also inevitable (especially when he was trying to, needed desperately to see Sam when he was lost in pleasure, loose and wanton and so so forbidden). But Sammy with a girl? Heck, for all Dean knows, Sam left for college a virgin (thank god).
What if Dean peeks through the crack in the door, and suddenly he can't breathe because those sounds are muffled because Sam's biting a pillow, knuckles white where he's holding fistfuls of it, and a blonde goddess with a leather halter on her hips is thrusting into him and they're glistening with sweat in the moonlight and all Dean can think about is how much he hates that woman, how much he wants to be the one holding Sam's waist in a bruising grip, how much he wants to feel Sam tight and hot around him.
What if Dean sees the woman - Jess, her name is Jess, his stalking has taught him that much - lean down, what if Dean hears her say "you like that, baby brother?" and what if Sam's cry as he comes gets Dean harder than diamonds and Dean has to leave, has to get out now because if he doesn't...
if he doesn't...
god, if he doesn't he might have to pull her off of Sam, because that should be him and Sam knows it and clearly she knows it too.
What if Dean had to come back the next night, because he couldn't trust himself that first time he broke in?
Okay all I'm saying is that if you didn't actually look at Jared Paladecki and just went off the average fandom physical descriptions of Sam Winchester (really tall, big tits, at least a little bit feminine) then Klinefelter's Syndrome Sam is actually a really good headcanon. I mean it falls apart if you actually look at Jared, I have no reason to believe he's at all intersex at all, he has traditionally masculine features and just happens to have tall genes and pecs, but my point is if you wanted to make Sam this particular flavor of intersex, it isn't that much of a leap. It does result in a Sam who is still very tall and well-endowed in the chest region.
And for the non-medical nerds, Klinefelter's means XXY chromosomes. They're generally born with typical male genitalia, but then they generally don't get normal male testosterone levels at puberty and will have elevated estrogen levels. So common traits include infertility, gynecomastia, low body hair, more feminine features, development delays, lower muscle tone, and for some reason, being extremely tall. Like. I've had a patient with it. And Jesus. His ass was about the same height as my head. That level of tall.
And. Because I'm a contrarian. The most delightful part of this headcanon/AU is that it would also mean Sam has a very small penis. As in like, child size because it never got that puberty growth. And given everyone and their mother thinks Sam Winchester has a horse cock, it is just delightful to me to come up with an AU where the entire point is that actually he doesn't.
John Winchester the man you are. You found the time to hunt and search for the YED, constantly worried about your youngest son being True Evil, parentified your other son, (forced) trained both sons to be hunters, drunk cried to your eldest, was weird with your eldest in basically every regard, repeatedly scolded your youngest for wanting an education, argued with him all the time, and occasionally sent your eldest away for weeks to months when he made a mistake. you were on a mission, not a good one, and you were bad at it, but you certainly managed your time in a creative way
This blog exists to encourage as many people as possible to post Supernatural fics about physical disablity during Disability Pride Month 2026 (July). Please use the tag #DisabilityNatural 2026 to promote your works, and tag this page so that I can reblog them all! If you write a fanfic posted on AO3, please also add them to the collection below:
DisabilityNatural 2026 Collection
Additional rules/FAQs below the cut:
What do you mean by physically disabled?
I am using the term "physical disability" for this event because the type of disability headcanons that are very well-represented in Supernatural fandom are mental illnesses and neurodivergency. This is intended to increase the number of fics for literally all other disabilities. So while for lack of a better phrase, I may use the term "physical disability," I'm not just referring to disabilities impacting mobility or anything like that. Sensory disabilities (blindness, deafness, etc), chronic pain, chronic illness, invisible disabilities, etc, are perfectly welcome. And you can absolutely make your characters be neurodivergent or mentally illΒ in additionΒ to having other disabilities. I just started this event to specifically address a lack of fics about non-neurodivergence disabilities, so I don't want it to be filled up with a bunch of fics about mental illness. Those are cool (and I've written plenty), but not what this event is about.
Rules/Guidelines:
The only requirements for this collection are that fics be a) about Supernatural, and b) contain physical disability. Both AUs and canon-compliant fics and disabilities are allowed.
All ratings, topics, ships, etc, are allowed. Supernatural fandom in particular is very often divided into destiel and wincest shippers, and I would like to make it explicitly clear that both groups (and those who don't like either) are allowed and encouraged to participate in this event. Please keep all ship wars out of this event and only leave respectful comments on each others' work.
Crossovers and early/late submissions will be accepted.
You do not need to be disabled to submit to this event! I, the person running this, am not physically disabled. I just want to encourage more representation.
Miscellaneous:
My main is @drowninginredink, so that's where all likes are coming from, and my spn blog is @schizosamwincester.
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So I finally realized why I can't quite get behind the popular headcanon of "Dean is straight except for Sam," at least not as it's usually written. I really don't care if he likes men that he isn't related to or not, but for some reason the whole idea bugged me and I couldn't figure out why. It just never fully sat right even when I wrote a Dean who was only into women.
It's the "straight" part. That's the problem. Even if Dean Winchester only likes girls, even if he doesn't have any non-familial feelings for Sam or John, even if he's completely heterosexual, Dean Winchester is still fundamentally queer. Because Dean Winchester is deeply aromantic.
The underlying narrative in a lot of these posts is that Dean is just a regular straight guy except for his incestuous desires, and like, yes, people can headcanon and write whatever they want, but as someone who is aromantic and allosexual, I just don't buy that. Sure, he loves girls. He wants to fuck girls a lot. He also displays absolutely no evidence of any romantic attraction for them. Even though he doesn't know the word aromantic and I'm sure he dies completely unaware of it, he would still be aware that he's Different.
I remember being 14 and having the thought "am I gay? I know I like guys, but I feel like I don't like them enough." Likewise, even if Dean has never, ever felt anything towards a man, he's at least going to have noticed that the way he feels about women is different than the way other men do. I mean, look at the biggest example of a heterosexual relationship in his life: his parents. Dean doesn't understand being so deeply in romantic love with a woman that 22 years later, he's still trying to avenge her. That's simply not a feeling that he has. I think by age 26, out of all his encounters with women, he will have noticed.
Don't get me wrong. If he's straight, I still do absolutely think he'd take issue with being called queer or gay. He'd still maintain that Sam doesn't count. He still would express disgust at the idea of having sex with any other man. All of that is still true. But just because he would try and keep up the facade that he's a normal straight guy doesn't mean that I want to. I know better.
So yeah, it isn't actually that I am attached to the idea of Dean as an mlm, I just can't get behind pretending he's essentially cishet. An aromantic heterosexual man does not experience attraction the same way as an alloallo straight man. That distinction matters to me.
samdean and rubysam all the way but also samjess to explore the deep-seated, gut-wrenching feeling of guilt that sam winchester gets about sex even when heβs doing nothing wrong
yes you throw up after your big brother fucks you and having sex with a demon makes you feel like youβre damned beyond redemption, but how about the fact that you feel like your chest is collapsing in after you sleep with your girlfriend who you love? whatβs going on with that sam?
This feels good, Sam tells himself. He repeats it in his head.
This feels good, god this feels good. It feels so good.
Anyone would give most, if not all of, anything to have Jessica Moore on her knees in front of them. She's everything the movies say California girls are: tall and tan with sun-lightened hair and a picture-perfect smile. She's everything locker room boys say good cocksuckers are: enthusiastic and confident with a well-timed twist and the deepest deepthroat he's ever felt.
It feels good and Sam is nauseous, one handed twisting firm but careful into Jess' mess of curls, looking at the wall covered in art they picked at a local craft fair in Palo Alto.
It feels good, but he's never liked having his dick played with, not really. It makes his skin hot and tight; makes him think about Oklahoma and how the plains truly do stretch from border to border, only interrupted by the earthfuck of oil rigs and the occasional McDonald's rising up like some executive had decided the land needed more height variation.
Makes him think about being touched in the dark and told, "See? It feels good." And it did, it really did.
You know... I've said many times that Dean has no idea that romantic attraction is even real, but upon further reflection, I think I was wrong.
Dean is extremely self-aware. It's easy to forget that he knows about his problems and bad coping mechanisms and general neuroses because he generally doesn't do anything to fix them, but he absolutely does know about them. Here. Have some quotes to prove it:
No Exit (2x06):
Jo, you've got options. No one in their right mind chooses this life. My dad started me in this when I was so young... I wish I could do something else.
Jump the shark (4x19):
You know, I finally get why you [Sam] and Dad butted heads so much. You two were practically the same person.
I mean, I worshipped the guy, you know? I dressed like him, I acted like him, I listen to the same music. But you were more like him than I will ever be. And I see that now.
The End (5x04):
I was wrong. Dean. I was wrong. I'm begging you. Say yes.
But you won't. 'Cause I didn't. Because that's just not us, is it?
There are definitely more, but these were the ones that were easiest to find because I wrote "self-aware" in my notes.
Dean has a lot of time to think. He routinely drives for twelve hours straight. He keeps a lot of his baggage to himself, and that means the thoughts are stuck rattling around in his brain instead. He can examine himself and his feelings and his problems over and over and over again. Just because he doesn't cope with them the way someone who's having these revelations in a therapy session would doesn't mean that he hasn't figured them out.
So with all that in mind, with how well Dean does actually understand himself... Why wouldn't he have noticed that he views sex and romance in a fundamentally different way than the people around him? The two biggest figures in his life, Sam and John, both loved women so much that they went on massive revenge quests after they died. They let their romantic love for people who were already dead completely uproot their lives. Surely Dean has noticed he's never felt that way about anyone, not even the hookups and situationships he liked the most.
Dean knows who he is. He knows that he's the hookup guy. He avoids baggage, strings, and feelings at every opportunity. It would make a lot of sense for him to do that because he's figured out that he just doesn't feel the same way about women as they usually do about him.
Dean Winchester is Dean Winchester on purpose. It's easy to forget that when you're someone who would never choose to be like that, but he very much did. So even if he does not have the vocabulary that we do and thus can't explicitly call himself aro, it makes sense for him to have created the "love 'em and leave 'em" part of his persona precisely because he knows he doesn't have romantic feelings towards anyone.
All that said, the pace at which he accepts it is definitely variable. He obviously knows he isn't interested in romance right from when we meet him in Season One, but he might not have come to the realization that other people actually are. It is probably a revelation that happens in stages, and I think there's a lot of wiggle room for when those happen and how he comes to terms with it. There's time for denial (I've definitely felt things for women, actually) and bargaining (other people can't possibly feel all that) and all that jazz.
The main thing is that I have absolutely said in the past that "Dean Winchester dies without ever learning that romantic attraction is real," and I do not believe that anymore. He may be stubborn, and he may not tend to actually change his behaviors, but he is too self aware to not have noticed them.
My most self-indulgent supernatural headcanon is that sometime when Dean was a teenager, he almost lost his left middle finger in a hunt. I'll be honest, I don't really care how. But it was damn near severed, bad enough that he actually went to the hospital for once. The feeling in it is still sketchy, the nerves having never really reconnected right, but he managed to keep it. Still, you can tell. Even years later, there's a ring of thick, white scar tissue around the base of the finger.
And that's how I can make a character who definitely doesn't know what aromanticism is, and who wouldn't exactly flaunt it even if he did, wear an aro ring.
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It's my birthday today, so let's shake things up. Instead of me asking you something, respond to this with a question that you want me to answer! And I will get to talk everyone's ears off all day. No limits or anything; just go for it.
- @schizosamwincester
HAPPY (belated) BIRTHDAY !!!!!!!
hmmmmmmmm
who do you think is a better match with sam? and/or dean? this can be in any way you argue for, platonic, shippy, best chemistry, best history, best friendship, best battle partner, etc. I'm curious on who you think is the best match up for them, platonic or otherwise !!!!
Okay well. I mean the answer is obviously each other. For better or worse, the Winchesters simply do not know how to function independently. They see each other as two halves of one whole. They do not want to exist without each other. And so regardless of how unhealthy they may be, or how often they misunderstand each other completely, or their tendencies to come up with an idea in their head of what their brother thinks or wants or needs that simply isn't true... if you've only ever wanted one person to be your partner, and won't accept anyone else, they are the best partner for you, just by default. But. I also think given we are both wincesty blogs in the wincest sphere, that's the most boring answer I could possibly give and thus shouldn't count.
So I'm going to use this as an opportunity to make an argument that's been in the back of my head for a bit, but I haven't actually gotten around to posting about yet.
Lisa is the best partner/match for Dean, because she understands him well enough to not try and make it last.
Lisa sees right through Dean to a degree that's... Like... I feel like it's kind of emblematic of the shows problems with women, honestly. They don't really understand how to write female characters, and so they just write her as perfect. She understands everything about Dean because like, isn't that what women are supposed to do? They're supposed to be good at all this emotional stuff. Obviously they can't fail to understand their men. Then they wouldn't be A Good Girlfriend. That's what good girlfriends do.
But. Taking Lisa as she is written, it is simply a fact that she understands Dean at his core. She knows he's not the kind of guy to stick around and never will be. That's why she tells him Ben isn't his kid. That's why when he asks to hook up again, she tells him absolutely not. When Sam comes back, what does she say? That she knows he's a hunter and not a construction worker, and so he should just go. That she knows a tied-down family man isn't who he is, and they can make it work this way, but she knows she can never make him stay.
Dean is a fundamentally aromantic character. Across the whole series, he shows a lot of desire to hook-up with women, but never the desire to actually settle down or date. Not romantically, and not platonically, either. And when he connects with Sam and Bobby again, he makes it very clear that he didn't want a stable partner and a happy home. He wanted Sam. And the only reason he actually went to Lisa and Ben and stayed with them is because Sam told him to.
Lisa is the best partner for Dean because she understands that there is no ideal romantic partner for Dean. That isn't who he is, and he never will be. As they say, "if you love something, let it go." And she does. Because ultimately, what Dean needs out of a love interest is for them to understand that they will never be what he wants or come first in his life.
So yeah. That's my hot take.
As for Sam? No character in the show has been anything close to the ideal partner for Sam. Absolutely none of them would be right for him. I mean, maybe Jess I guess, but we don't see enough of her to know that for sure. Lucifer is the most interesting partner for him because of how convinced he is that he's Sam's perfect match, but it's pretty obvious that Sam doesn't like him back one bit. I don't know who would be good for Sam, but not any of these characters. Not that it really matters, when he'd reject anyone who isn't Dean, anyway.
Okay. Lisa Braeden is aromantic. Lisa/Dean is in fact aro4aro. Why? Let's go.
Who the hell still goes on about a hookup they had 9 years ago? Like. Okay. With Dean it makes sense. He has no life outside of hunting, Sam, and sex. I can understand Dean still being like "If I'm going to die, I want to fuck Lisa again first." But Lisa has a life. She has a child and friends and a stable job. What woman with all of those things talks about one weekend nine years ago so much that when Dean appears everyone is like "oooo. That's the guy she always talks about." I don't think an alloromantic woman would talk that much about a hookup that presumably had nothing romantic about it to her respectable married friends. The best night of an alloromantic woman's life would probably involve a boyfriend and romance, not just crazy sex. Which brings us to my next point.
She deliberately sought out guys who are not going to be available for romance. When she says that Dean isn't Ben's father, it was some other unattached drifter, she also says, "I had a type. Leather jacket, couple of scars, no mailing address." And yeah, a lot of us think she was lying about the first part, but there's no real reason for her to lie about the second. Which, as an aromantic allosexual? What a fantastic strategy. 10/10. And like, let's be really clear here: looking at what we know of the timeline of her life, she went right from picking up guys who would never be anything other than one nights stands to being a single mom and presumably being way too busy for that. For all we know, she might never have actually had a romantic relationship ever until Dean.
She seems really happy with being a single mother. Like... If I got pregnant by someone I knew I was never going to see again, I would be going to Planned Parenthood because I know I couldn't handle that alone. Lisa could have gotten an abortion. She didn't. That raises the possibility that she wanted to be a single parent, potentially even more than she'd want to have a kid with a partner. That's true for some aromantic people. Hell, while now I wouldn't want that because I'm just way too disabled for that, as an aro kid I had multiple different fantasies about it. Like, usually in media being a single mom is trashy and depressing and sad. It's honestly really interesting that Supernatural, the misogyny show, has such a positive depiction of it with Lisa.
She consistently understands Dean and his thought processes and priorities incredibly well. It's easier to get people if they're similar to you. And I think anyone seeing this post probably already agrees that Dean is aromantic.
The entire dynamic of Lisa and Dean getting back together is... weird? To be clear, their relationship up to that point is: a) they hook up once, b) a decade later, he saves her kid, c) a year and a half later he shows up on her doorstep crying and then leaves, d) he comes back and she lets him live with her as her partner for a year. That is not the normal trajectory of a relationship. At no point is there any dating there. But if you ask me, it makes a lot of sense for an aro who doesn't really understand romantic relationships to begin with.
I'm leaving list format now so I can really dig into this. Let's start with a personal anecdote from me. When I was in high school, there was this guy. He was pretty lonely because he was disabled and, you know, kids are assholes. It was pretty well-known that he would ask out pretty much any girl who was ever friendly with him. And like, not in a creepy wayβif you said no, that was that. He was more than happy to stay friends. Most of his friends were girls in fact, and they'd pretty much all gotten asked and then moved on. Anyway. I got asked. And unlike all the other girls, I went "well. Relationships are a thing people do. I think he's attractive, and that's all crushes are, right? Sure, I'll say yes." I didn't bother examining if I actually had romantic feelings for him (I didn't think those existed, I thought all crushes were purely about attraction to someone's appearance), I just went with it. Needless to say, I didn't know I was aromantic yet.
I'm not convinced that Lisa knows she's aromantic, either. I think when she did all her hookups, she told herself, "I'm just young and having fun and don't want to be tied down right now." And then once Ben was around, she said that she was just too busy for a relationship. A lot of aromantics and asexuals continually push off realizing that they don't want the same things as other people with excuses like "oh I'm just too young for that" or "I'm too busy with school" or "I'm trying to get started with my career" and it takes them a really long time to realize that even when all of those aren't true anymore, they still don't actually want romance and/or sex. I think because Lisa went right from "I'm too young" to "I'm too busy parenting," she probably still hasn't had that realization. She assumed that eventually she'd find the right guy and want to settle down. And then Dean Winchester ended up right in front of her, and she went "I guess this is it."
If we look back at 3x02, her first reaction to the idea of having anything to do with Dean again is "hell no." That makes sense. I think that's the normal reaction if a hookup suddenly wants to get together after eight years. She only changes her tune because he's really good with her kid. He wishes Ben was his own kid, even. And when that's the case? Well, Ben could use a male role model. She's always wanted that for him. And it would be nice to have a coparent. Plus hey, Dean needs this too. He could use a place to stay and a thing to do and someone to support him. Ben would have a Mom and a Dad like he's supposed to, and Lisa would have a boyfriend, like she always said she would eventually when she got around to it. There's a great opportunity for everyone right in front of her. She might as well go for it.
At no point do either her or Dean realize that actual feelings for each other played no part in it. They both wanted to be coparents who were friends and fucked, and they both figured "hey, that's basically what romantic relationships are, right?" They didn't mean to seek out an aro4aro QPR arrangementβthey just both fell into it and assumed it was normal.
Anyway full disclosure that, a lot of this draws off my own personal experience of what being an allosexual aromantic is like, so other aromantics might look at this and go "no actually she doesn't sound aro at all to me" and that's fair. Also I have never been alloromantic, so when I say "I don't think an alloromantic would do what Lisa does," that is fully a guess. I do not actually know.