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#saileen
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I can't find it but to the person who posted that Sam and Dean should've fought in 15x19 while they grieved Eileen and Castiel respectively, I am kissing you on both cheeks respectfully or giving you a high five if that's not your style.
The idea of Sam saying, "I lost Eileen!" and Dean rebuts with, "well I lost Cas!" and Sam going, "that's not the same thing!" and Dean landing the killing blow, "of course it's not. At least you got to tell Eileen you loved her back!" all of that exploding in the stillness of the bunker, of the world without life, is fucking beautiful cinematic astounding magnificent glorious I am living for it.
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winchestergifs · 1 month
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Sam Winchester & Eileen Leahy ✣ 3.17.21
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beansprean · 6 months
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THANKS FOR ANOTHER GREAT NOVEMBER 5TH EVERYONE!!
[prints, stickers, etc available!]
Support me on Patreon or send a tip on Kofi!
(ID in alt and under cut)
ID: Dean, Castiel, Jack, Sam, and Eileen standing in a line against a damask-papered wall in the stylings of one of those haunted house photos, reacting to a scare offscreen. Dean is hunched over at the back of the line and screaming open-mouthed, both hands gripping onto the back of Cas’s trenchcoat like reigns. Cas has lurched forward, coat stretching out behind him in Dean’s grip, instinctively putting two arms protectively around his son. His right hand is in front of Jack, turning him away from the scare, and the other is cupping the back of their head as if to tuck them under his chin. Cas’s mouth is pressed shut but his eyes are wide and startled. Jack looks surprised and fascinated, the right string of their hoodie falling out of his mouth as he stares at the scare offscreen. They are half turned away from the scare at Cas’s nudging, right hand resting on Sam’s arm in front of them and left holding his left hoodie string in a fist. Sam is screaming open-mouthed, shoulders pulled up to his ears as he straightens to his full height like a startled cat. He is holding onto Eileen in front of him with both arms, clutching his own hand just under her chest and squishing her tightly to him in fright. Eileen, obviously having not heard the audio cue that scared the rest of them, looks confused and a little irritated, hands covering Sam’s over her torso. She is startled only by Sam’s sudden bear hug as his jump launches her own breasts up toward her chin. /end ID
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seasononesam · 1 month
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It's okay. It's okay.
15x09 "The Trap" Deleted Scene
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xofemeraldstars · 4 months
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✨ HAPPY NEW YEAR !! 🎉🎆🎇
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sjonni33 · 7 months
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portrait - suptober day 5
hehehheh took it literally and went with the family portraits!! dean and cas, bobby and crowley, rowena, sam and eileen, charlie and claire and jack :) i wanted to add sooooo many more sjsjsjsj but yeah
[prints & stickers] [give me a tip]
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avalonlights · 6 months
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Been trying to finish this drawing for 3 years. I know in my heart they're alive and together. ❤️‍🩹
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Sam Winchester Appreciation Week - Day 5: Favourite Sam Relationships ↳ Sam & Eileen
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castielsprostate · 6 months
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it's not true love if they don't try to kill each other at least five different times for different reasons
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winchestress · 1 year
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12x21 | 13x01
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zepskies · 3 months
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Show Me - Part 1
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Pairings: Dean Winchester x Plus-sized Latina!Reader || Sam Winchester x Eileen Leahy (background)
Summary: Dean meets your infamous ex-boyfriend at a fallen hunter’s funeral. You just forgot to mention that he’s a hunter as well. Maybe because he still has the power to get under your skin…in the worst of ways.
AN: Another story for the Espresso-verse! This is set after “Devour Me,” and plays on plot threads in “Midnight Espresso” and the flashbacks in “In Bad Weather.”
Word Count: 3,100
Tags/Warnings: Angst, body shaming, body insecurity, protective Dean.
☕ Midnight Espresso Masterlist
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Part 1: “Objects Are Closer Than They Appear”
Hunter funerals aren’t supposed to be lively affairs.
Alicia Jackson is special, however. She’s known so well throughout the hunter community that news of her death creates a kind of reunion at her mother’s house after the funeral, not unlike Asa Fox’s wake last year.
Even you had known Alicia, though not particularly well. You met her through Eileen. They’d called for your help on a ciguapa case a few months ago, and ever since, Alicia had insisted on buying you a beer anytime she was in town.
So today, Sam and Dean are really supporting you and Eileen by coming along.
Alicia’s mother, Martha, is a lovely Haitian woman in her late sixties. Her house is modest, but welcoming. She’s a gracious host to have so many rough and tumble hunters in her home.
The wake is mainly gathered in the backyard, where plastic tables and chair have been set up. Most of the hunters have collected into groups of the ones they know, sharing stories, laughing, eating, and drinking.
You’re in the kitchen with Martha, as you’ve offered to help her put out some more beers on the table outside. The smaller woman falters for a moment when she glances at a framed picture of her daughter on the wall. Alicia was beautiful, with coal-dark skin and soulful brown eyes she’d inherited from her mother.
You end up holding Martha’s hands in comfort when she nearly crumbles again. Your heart breaks for her. Even if you hadn’t been that close with Alicia, you’d hope that someone would take care of your own mother in a situation like this.
“She just has so many friends,” Martha says, with a tearful chuckle. “I never realized…”
“We try to look after each other,” you reply, smiling. “Everyone here knew your daughter, if not personally, then by reputation. And guaranteed, all of them have at least one good story to share.”
Martha nods. Somehow, she’s able to smile through her tears as she pats your hand. 
After spending a few more minutes with her, you predictably find Dean by a long table of hors d’oeuvres and desserts.
“Babe, you gotta try these mini quiche. They’re delicious,” he says, after popping another pastry into his mouth. You can see that he’s eaten nearly a whole tray while he’s been waiting for you.
“You realize we’re at a wake, not the Golden Corral,” you lightly tease. He shrugs.
“Still gotta eat, right?” he says.
His capacity for food knows no bounds, but you love him for it.
You glance over at Sam and Eileen chatting with a small group of hunters under the shade of a tree. They’re sitting close together at a picnic table. Your lips form a subtle smile, and you lean in close to Dean.
“Look at your brother, being a supportive non-boyfriend,” you say. They’ve been loosely “dating” for weeks, though you aren’t sure they’ve put an official label on what they are together.
Dean’s expression turns both fond and amused. “Think they’ve sealed the deal yet?”
You glance over at him. “What do you mean?”
“You know…” Dean waggles his brows suggestively. You do know what he means, and you playfully smack his chest. Mostly to stop him before he starts making lewd hand motions.
“Come on, that’s none of our business,” you reply. Inside though, you’re wondering the same thing.
Dean spies the look on your face and smirks.
“See. You’re curious too,” he says. He gestures at your face with the same hand that holds a bacon-wrapped cocktail weenie. You have to raise a hand to fend him off when he tries to veer it into your mouth.
“Don’t point at me with your sausage,” you quip.
“Funny. I’ve never heard that particular complaint outta your mouth before,” he smirks.
He eventually gives up on feeding you and eats it himself. His warm gaze is still on you though. You start to blush.
“Again, we’re literally at a funeral reception,” you say, despite your growing smile.
His gait becomes more flirtatious as he leans in to whisper in your ear.
“Like I said. We still gotta eat, don’t we?”
You splutter laughing, though you attempt to contain it behind your hand. Dean’s chuckle resonates through you when he pulls you in by your waist. His thumb brushes your hip. He’s not so much into PDA, and certainly not as “touchy” as you, but this much will do for now. You lean into him in turn.
He finishes off his umpteenth hours d’oeuvre and sets his nearly empty beer on the table. After letting loose a barely stifled belch, he mentions something about finding a bathroom.
“Dogs are already barkin’, huh?” you tease.
“Yep,” he freely admits, patting his stomach. “Give me five minutes…or ten.”
He squeezes your arm in parting before he takes off down the hall at a purposeful pace. It leaves you to contemplate the mini quiche.
Damn, they do look good. You bend over the table slightly to peruse your options, when a familiar voice drawls behind you.
“Still got a fat ass,” he teases.
You freeze. Slowly, you straighten up, and you turn to blink in surprise at the man who stands there, holding a beer and wearing a playful smile.
Yours is polite at best as you try to get through your shock.
“Carter,” you blurt out. What the hell are you doing here?
He greets you with an incline of his head. The way he says your name is both familiar, and a little unsettling.
You cross your arms and lean back on your heels. “You knew Alicia?”
“We tangled a few times,” Carter replies with a nod. His smile laces with a bit of innuendo, but his eyes have just enough heaviness to convince you that he really did have some kind of relationship with Alicia.
Oh, Ali. You could’ve done better, you think. You wish you’d known that tidbit of information when she was alive. You would’ve warned her.
“I’m sorry for your loss then,” you say. Carter nods again. A silence falls awkwardly between you two.
“Is that all we’re gonna say to each other?” he asks. “It’s been…what, a couple years?”
“Almost four,” you supply. You and Carter had ended just a few months before you met Sam and Dean, a little over three years ago now. You and Dean hadn’t started dating until last year.
“All right,” Carter says, rubbing at his chin. His gaze roams over you with a slight smile. They take you in from your high-heeled boots and jean-clad curvy thighs, to your green blouse, laced loosely in the front. You’d decided to dress a little nicer for the occasion.
“You know, you look the same,” Carter says. His head tilts. “But different somehow.”
You raise a brow. “Different?”
“Yeah, like…” He draws closer and leans on the table beside you. He sips at his beer. “Confident. Like you’re not hiding yourself anymore.”
He mimics the hunch of a turtle in its shell.
“You used to be like a little mouse sometimes,” he adds with a light chuckle.
You know he means to be teasing, but you’re not laughing. If you’re not hiding anymore, it means you’re not trying to bury yourself under shapeless clothes, along with much of your inner self.
“Don’t you think that’s a little tight?” he’d asked you once, before you two went out together. It wasn’t the first time. (And it wouldn’t be the last.)
“I’m just saying,” he would often say. “You might feel more comfortable in something a bit looser. Cover these up a little.”
You remember how he’d squeezed the softness around your sides or your stomach. You also remember a well of anxiety in your chest that had made you feel almost grotesque when you’d studied yourself in the mirror afterwards.
Objects are closer than they appear…
You remember agreeing with him. Changing clothes. Drowning yourself in crewneck shirts and breezy buttoned-downs. Always wearing pants and baggy shirts to bed. Thinking all of this was to make you comfortable, and not the man who didn’t really love you.
So now, you give him a passive look as you take Dean’s forgotten beer and finish the last sip. Carter wears a hunter’s red plaid over jeans and his old leather boots. His blonde hair is shaggy around his ears, his face a little rough with stubble, his eyes still a deep blue.
He looks exactly the same. He probably is the same.
He’s right about one thing though. You’re not the same.
“We’re not in the profession of hiding,” you finally reply. “Guess I just got tired of it.”
Carter seems to sense your shift, and maybe, what you’re really saying. His smile falls into contemplation. He crosses his arms.
“Did I spot you with one of the Winchesters earlier?” he asks.
You nod. “Yeah, that was Dean.”
Before you can add the boyfriend part, Carter whistles lowly and shakes his head.
“I’d steer clear of them if I were you,” he says.
You quirk a brow. “Excuse me?”
“You heard me. Those two are walking hurricanes of bad luck, blood, and mayhem,” Carter says.
“You don’t even know Sam and Dean,” you counter. Your voice is sharp and your brows knit together in thinly veiled irritation. “So I suggest you shut your mouth and steer clear of me.”
You set the beer bottle a bit hard on the table and mean to brush past him. You spot Sam and Eileen again, still sitting in their same table under the tree. You aim to head over there to wait for Dean, but a hand wraps around your arm.
“Come on, sweetheart. Don’t be like that,” Carter frowns.
“I’m not your sweetheart,” you tell him. You’re discreet in the way you try to twist your arm out of his grip. You glance around to make sure no one’s watching you two. The last thing you want to do is make a scene here, but Carter is being a stubborn ass.
Even though you manage to wrench out of his hold, he grasps your hand next to stop you from pulling away. He looks down at your hand, brushes his thumb over your skin. His gaze looks heavy, almost melancholy.
You know that funerals tend to bring out the sentimental shoulda, coulda, woulda in hunters, but you think he might be looking back on your time together with rosier glasses than he ought to be.
“Look, I'm sorry. Can’t I at least get you a drink? We can catch up,” he says.
“Consider me caught up,” you toss back. Frustration begins to set you on edge. “I don’t know why you’re pushing this. I mean, God, we weren’t even good together.”
At that, his grip tightens on your hand. Confusion and denial cross his face.
“That’s not true,” he protests.
Unbidden, you’re forced to remember the weeks you and Carter spent in Miami, where you’d met him. You remember how he’d convinced you to leave with him after his hunt was done, and to leave your family behind. A decision you regretted to this day…
You lean in closer just to whisper hotly. “You know it is. We didn’t have a relationship. We had a transaction, in which you liked what I could do for you. But you never loved me. You never even really knew me.”
At that, his hold finally loosens in his shock. You take the opportunity to slip your hand out of his. Another familiar hand rests along your lower back, and a firm wall radiates warmth behind you.
“Hey, party people,” Dean says. He gives Carter a “pleasant” smile, and you a more genuine look. You okay? it says.
You let out a subtly relieved breath and nod. “Hey, was just gonna go check on you.”
“I’m good,” Dean says. He looks over at Carter, whose expression has cooled considerably. Still, Dean inclines his head. “Hey, man.”
“Yeah,” Carter says. His tone is bland, until his gaze slides back to you.
“Don’t tell me you’re shacking up with this one now,” he says, leveling a finger at Dean. Then he gestures across the lawn, over at Sam. “Or is it the former anti-Christ over there?”
Both you and Dean bristle. Your temper has a thin fuse right now, and while you still don’t want to make a scene, you might have to make an exception.
“Why don’t you remember where the hell you are and have some decency,” you hiss. “Do us all a favor and fuck off.”
Once again, you try to walk past him. This time when Carter grabs you, it’s because he smarts at you getting the last word. A sharp breath escapes you, and Dean intervenes with a firm, warning grip on the other man’s wrist.
“Hey, you wanna act right, before you make yourself a problem?” Dean says. His face is relaxed, but behind his eyes are a very real threat. “I got no issue laying you out right here, in front of all your buddies.”
Carter has a moment of indecision. He notices a few pairs of eyes drawing their way, and so he lets go of you, even as he sneers at Dean.
“Shove the Prince Charming bit, asshole. She ain’t a damn princess,” Carter snaps. “She don’t act like one, and she definitely don’t look like one.”
You roll your eyes at his spite, but Dean can’t quite let that one slide off his back. 
His grip tightens on Carter’s wrist as he pulls him in. He pats Carter hard on the back and smiles as if they’re old friends. But really, it just gives him the vantage point to speak lowly near the man’s ear.
“All right, douchebag. Keep talking shit. I’ll bet that’s how you’ve gotten this far in life,” Dean says. “But touch her again, and I’ll break every damn bone in your hand. And maybe, I won’t stop there.”
He tilts his head, so he can see the glimmer of intimidation hidden well behind the other man’s eyes. Then Dean lets him go. He turns and lays a hand at the small of your back. The two of you fall into step together while walking across the lawn in the backyard.
“You didn’t have to do that,” you say quietly.
Dean frowns and notices the way your gaze has lowered. His hand moves around your waist and squeezes to get your attention. Without him realizing, it just reminds you of the way Carter used to point out the thicker curves on your body.
Cover these up a little.
“Hey, you okay—”
“I’m fine, Dean,” you say, easing out of his hold.
It leaves him feeling unbalanced, and a bit put out. Dean remains quiet as he follows you over to his brother’s table.
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“Are you all right?” Sam asks you, discreetly, but with concern. The wake is coming to an end, and by now Dean has filled him in on your run in with your ex, Carter Hall.
You give Sam a nod and a smile that doesn’t quite reach your eyes.
“Yeah, I'm good,” you reply.
Dean is quiet. He stands beside you with his hands in his pockets. Eileen has invited you and Dean to join her and Sam at a nearby bar to keep the evening going with a few other hunters, but this has already been one hell of a day. You’re ready to make the long drive home and call it a night.
Eileen’s also agreed to take Sam home (eventually). You notice how they share smiles, how Eileen ducks her head with the beginnings of a blush. You’re happy for them, even as you and Dean part ways with a more stifled silence on the way back to the car.
It’s late, and it’s cold. You walk beside him with your arms crossed, just to brace yourself against the windchill eating through your jacket. You glance over at your boyfriend and feel a measure of remorse for the way you brushed him off earlier. You have a feeling that’s part of the reason why he’s quiet, giving you your space.
You decide to close the distance. You sidle up closer and curl your arm around his. Your hand slips into his as well, threading your fingers together with Dean’s.
He looks over at you with a slight raise of his brows. His lips quirk at a smile, and his hand tightens on yours. You’re able to give him a more sincere smile in return.   
“Can I tell you something?” you ask.
“Yeah,” Dean says.
You look up at him and bite your lower lip. “I’m starving. I never did get to try those quiche.”
It only takes a moment for you to devolve into a quiet giggle. It’s infectious, and Dean laughs with you.
“Okay, we’ll stop somewhere,” he nods. Though his eyes widen in realization. “Damn, that means you haven’t eaten since, what, this morning? Before the funeral?”
You mentally count back the hours, and you have to agree with a sheepish nod. Dean shakes his head in disapproval.
“Come on, sweetheart. You should’ve said something.”
You shrug, even though you know he’s right. Your free hand curls around his bicep, and you lay your head against his arm. He looks down at the top of your head and heaves a sigh, despite his lingering smile.
Though the peace you’ve brokered is soon interrupted.
Dean had to park down the road of Martha Jackson’s house. Two cars down is Carter, who’s about to climb into his old Honda Civic.
Damn. He’s still driving the same piece of shit too, you note. His head raises, and as if he knows he’s being watched, his attention turns toward you and Dean. You don’t allow yourself to react, other than staring across the way, directly at Carter. You wait until he looks away first, opening his door and getting into his car.
You expel a breath and brush your thumb over the back of Dean’s hand.
“Let’s go,” you say.
Dean nods. He guides you toward the passenger side of the Impala, but his gaze lands beyond his car, to the Honda still parked and warming up. He finds Carter’s gaze through the front window for a moment.
It’s Carter who once again breaks first; he revs the ignition and peels onto the street, and down the road past them without looking back.
Dean's lips curve. Bitch.
Shaking his head, he rolls his shoulders and rounds the car towards the driver’s side.
He’s more than ready to go home.
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AN: *sighs* Okay, originally this story was going to be a one-shot, but it just got too damn long. Let me know what you think of Dean finally meeting her ex-douchebag, Carter.
Part 2 (coming next week) will include all the angsty hurt/comfort and smut to come...
Next Time:
“I’ll just speak for myself then,” he says. His hand trails lower... “If you need me to remind you how beautiful you are, how goddamn sexy…then I got no problem showing you.”
His hand moves down the soft slopes of your body and comes to rest at the curve of your waist. Hearing your faltering breath, Dean pulls back so he can see your face.  
“Let me take care of you for a change,” he says. His lips pull at a grin, and it makes you smile in turn.
You take his face in your hands and bring him down to you for a kiss, languid and a bit devouring. It makes heat lick up Dean’s spine.
“Okay,” you whisper, close to his lips. “Show me.”
Keep Reading: PART 2
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Series Masterlist
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Dean W. Tag List:
@hobby27 @kazsrm67 @letheatheodore @agothwithheavysetmakeup @jacklesbrainworms @foxyjwls007 @wincastifer @iamsapphine @simpforbuckyb @vanillawhiskeyflavoredkisses @roseblue373 @this-is-me19 @emily-winchester @spnexploration @deans-spinster-witch @deans-baby-momma @iprobablyshipit91
@melancholictearz @nic-kolas @sanscas @sleepyqueerenergy @wayward-lost-and-never-found @thewritersaddictions @just-levyy @samanddeaninatrenchcoat @deanwanddamons @antisocialcorrupt @lacilou @adoringanakin @theonlymaninthesky @teehxk @midnightmadwoman @brianochka @branj19
@agalliasi @venicesem @chriszgirl92 @lyarr24 @ladysparkles78 @solariklees @xsophianicolex @deansbbyx @candy-coated-misery0731 @curlycarley @sarahgracej @bagpussjocken @deanfreakingwinchester @chernayawidow @beskarfilms @mimaria420
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winchestergifs · 5 months
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STACKEDNATURAL ⇉ 120.5/327 (part 2)
15.6 Golden Time Written by Meredith Glynn Directed by John F. Showalter Original Air Date: November 21, 2019
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seasononesam · 11 months
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supernatural meme: (6/9) relationships | sam and eileen 
Feel free to drop a line if you ever need anything...Or even if you just want to hang out. You can't call me, though. Okay. I mean, you could call, but I won't answer.
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xofemeraldstars · 10 months
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SUPERNATURAL -> 15x17 // 12x21 // 13x01
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bitchslappin · 11 months
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sampegger · 4 months
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i have no idea if this is going to make any sense but. as an enochian speaking sam truther. if sam only ever learned most of the enochian he knows from lucifer in the cage. and that's just because he was forced to spend so much time with him and he was never really aiming to learn enochian himself. do you think that him working on improving his sign language for eileen is a deeply personal thing to him. like he loves her so much and this time he is learning someone elses language not out of necessity but out of love commitment and devotion. sam choosing to learn someone elses language this time around because he loves them after years spent learning enochian through lucifer just feels so... intimate and loving to me. do you hear me. do you guys understand what i'm saying. i'm ill.
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