Warnings: fluff, mild angst, Dean being a jealous bb
S/P/N- Sister’s Preferred Name.
Word count: 5k O_O
Summary: Dean, trying to get accustomed to Y/N’s family and her life in Boston, finds himself worrying about their very own lives together and what the future holds. Will he manage to find a permanent position in her life, or is it all just a role he must play for these two weeks?
Dean prays his nervousness doesn’t show in the weak smile he
offers the table of gleaming faces. They all stand as the three of them
approach, all with welcoming smiles, all eyes trained on Y/N as she walks to
them like a prodigal daughter returning home after so long.
S/P/N goes in for an immediate hug once she’s close enough and
engulfs her little sister, squeezing the life out of her. He tries not to
chuckle at the way Y/N groans—countless stories about their childhood together,
about how close they were and unbreakable bonds and up until today Dean has
never once met S/P/N, but he can’t help but find the way she treats her sister
The grin on her face is wide as she pulls away. “Look at you!” She
says, eyes raking up and down Y/N’s face. “You’re so different now, oh my God!”
“Please don’t start with me, we only just got here.” The y/h/c-haired
girl replies as she straightens out the creases in her skirt. Before she can
even get another word out, her mother is at her side, an ambient smile gracing
“Well, S/P/N’s not wrong.” Her voice is a deep baritone, husky and
rich as she gives her daughter a kiss on the cheek then turns to the boys. And
that’s when the anxiety comes flooding back.
A queasiness in his stomach, a twitch in his jaw—something basic
and miniscule like breathing or blinking, something he does unconsciously,
suddenly feels mechanical. Forced. But the elder Winchester masks it with an
amiable smile, the corner’s of his eyes scrunching up. Y/N’s mother’s eyes then
travel to his own and her face lights up. “Dean…”
“Marilyn…” He smiles.
They hug like their old
friends, like this isn’t their third (fourth?) time meeting; that’s the kind of
person Y/N’s mom is. Everyone is her friend. Everyone is adored company rather
than a burden, and Dean can’t help but feel a bit intimidated by this level of
kindness because God, could he pick a leaf.
Her face folds like dough when she simpers. “looking dapper as
ever. Sam, don’t think I’ve forgotten you.”
S/P/N cuts in, earning the elder Winchester’s attention. “So
you’re the esteemed-Dean, huh?” She asks, brown eyes scrutinizing him; despite
being her blood, she looks nothing like Y/N. A few join similarities here
courtesy of genetics and maybe some shared habits, but Dean knows Y/N enough
that he’d be able to distinguish her if she even had a twin.
“Wow.” S/P/N turns to Y/N with a ribbing smile. “You really know
how to pick ‘em.”
“Shut up.” Y/N rolls her eyes, but the
pink-tint in her face is undeniable—so she’s nervous, too. Good. Someone has to be, he thinks. Maybe Y/N can take his place in
this apprehensive state, salvage him from his feelings.
“The stories I’ve heard about you…” S/P/N says fondly. “Welcome. It’s
great to finally meet you.”
“Yeah, likewise. Your sister goes on and on about you.”
Dean’s expression then shows hwo taken abck he is at that very
moment: his eyes widen a smidge and his brows quirk. Turning to Y/N, he asks, “Does
The young hunter’s face is a deep red as she shoots her sister a
dangerous look, jaw clenched. “Really?”
Rolling her eyes, she then links her arm with his. “Come on, Dean.
There’s still a ton of more people we have to meet.”She says as she turns and strings him along with her.
They scuttle aside, leaving Sam deeply invested in chatter with Marilyn as they
venture into the crowd. Amused, the elder Winchester’s smirk doesn’t leave his
face as they move.
He leans in, voice hushed. “So, you talk about me a lot, huh?”
“Shut up, Winchester.”
“That’s not a no.”
“It’s not a yes, either.”
“Sure, whatever helps you sleep at night.”
Y/N then halts to a stop and whips around to face him, face
constricted with irritation. Satisfaction floods Dean at the sight; pretending
they’re in a relationship doesn’t mean abandoning his liking for razzing the
young-girl. If anything, he reasons, it’s a catalyst.
“Dean,…”She warns, her voice as thin as ice. “I’m warning you…I’m
not one to shy away from slapping you right in front of all these people?”
“You wouldn’t do that to your boyfriend…”Smirking,
he goes to wrap his arms around her waist and pulls Y/N in, tipping his head
down to look at her. Her expression then falters for a moment; her face falls
and the fire in her eyes fades; but its brief, almost indiscernible, because
seconds later her pout resurfaces.
Their bodies are flush together, her nimble waist caged in his
hands, and Dean tries so hard to ignore the way the tips of his fingers heat up
at the contact.
Instead, he chuckles and loosens his grip. Y/N manages to slip out
as she rolls her eyes—even then, her blush is still evident.
“Come on…”She links Dean’s hand in
hers, and leads him over to another table crowded with some cousins and aunts.
The garden is dotted with various people, all smiling when they see her, all
going in for hugs and pecks on the cheeks and all giving such sly smiles when
Y/N says that Dean and her are dating. Some congratulate them, some, whom Dean
has had the pleasure of meeting before like Y/N’s cousin Garth, hold a teasing
glint in their eyes.
They talk to relatives and uncles and eerie aunts who, right in
front of Y/N, try to hit on Dean. The garden is buzzing with life from all
ends, music floating amongst chatter of guests, people dancing, and as she talks more and more with old
friends and relatives, he can see the young girl gradually unwinding.
Her smile, ever-present and as radiant as star, grows with each
second, with each interaction. She’s mirthful. Happy. If that’s the case, Dean
wonders, then why was she so reluctant about driving out to Boston? Why had Y/N
shown the idea of coming out here such disdain? The question swims in his mind, but that’s as
far as it goes. Dean doesn’t bother asking. That’s not his focus now—his focus
now is playing his part and helping her get through these two weeks without any
setbacks, and so he allows himself the luxury of sitting back and indulging in
the buffet with Y/N. Their earlier hunger returns with a vengeance once they
spot the table lined with various foods.
They’re stacking piles of pastries onto their plates, when all of
a sudden comes a voice.
“How did you two meet?” Uncle Gary, a burly bull trapped in a man’s
body, inquires. He’s got hair as grey as the ash on his cigar, and each time he
speaks, the thick mustache atop his lip wiggles like a caterpillar. His wife,
Steph, stands by his side, eagerly staring and waiting for a response.
“Uhm..”Dean’s gaze slides to Y/N. She looks back at him, a brief
horror flashing on her face. For a few seconds, they panic. Shit.“We met…”
“In the park!”
The elder Winchester, shocked, glances over at his girlfriend.
She’s smiling at her uncle, her cool demeanor seamlessly in place. If you look
hard enough, you can see the glint of pride in her eyes from just saving their
Uncle Gary’s thick grey brows quirk curiously. “In the park?”
“Yeah…” Y/N affirms. “Well, by the park. I was, uh, walking my dog
one morning when all of a sudden this car comes speeding out of nowhere as
we’re crossing.” She casts cursory glance at Dean, who tries not to smile, both
in appreciation and subtle arrogance.
“Yeah.” He supplements, earning the attention momentarily. It’s
kind of funny how synchronal they are—a close call like that, teetering along
the line between exposing themselves, but Y/N manages to redeem them, and Dean,
like a dancer moving to the tune of her symphony, follows without a beat.
“See, I was on my way to
work that morning. I was late, so you can imagine what a rush I was in, right?
So there I am, cursing to myself as I speed down the road, one hand on the
wheel and the other on my tie, when this fuzzy little poodle—“
“Jack Russell.” She corrects. “ He was a jack Russell.”
Dean raises his finger in benediction. “Right, Jack Russell. So—all of a sudden, he
jumps out onto the road and I’m in shock. “
“Luckily, with quick reflexes like Dean’s, he managed to swerve
out of the way. He misses him. ” The young girl plays the role so earnestly,
her furrowed brow and weary eyes expression selling her distress. “God, poor Kujo
was shaking like a leaf. “
“So, Y/N, pissed as hell, tries waving me down. She’s running
after my car until I finally pull over and she comes up to my window, and just
starts exploding.” Dean’s eyes widen for emphasis, his hands waving in the air.
It’s a known trait of his. Whenever telling story, to try and spice thing up or
make them seem much more exciting than they actually are, the elder Winchester
will flail around and pull faces, and Y/N won’t admit it, but she find it
“She’s going on about calling the cops and road rules and safety, but
at that moment all I’m focusing on is how goddamn y/e/c her eyes are.” He
explains. He doesn’t notice that, as soon as the words leave him, the young
girl’s face flushes red. He goes on, says something more, something that makes
Aunt Steph’s face fold and crease like cookie dough as she smiles, and then
finishes off with a firm arm around her shoulder.
He gives it a firm squeeze, his eyes crinkled with a smile. “Long
story short: I didn’t even show up for work in the end.”
“Wow.” Aunt Steph’s grey eyes go wide like planets. “Unconventional
“That story was a rollercoaster from start to finish! Loved it!”
Uncle Gary, smile engulfing his face, slaps a friendly hand onto Dean’s
shoulder who glances at Y/N.
The pair shares a confided glance, their pride shining in the way
they smirk at each other. They’ve pulled it off.
The elder Winchester offers a proud smile, fighting the urge to
turn to his partner, to pull his lips back in a teasing smirk, for the smugness
in his eyes to say I told you so, I told
you the doggie hit-and-run would sell. Instead, however, he focuses on
Uncle Gary telling him about his very own Terrier that nearly got hit by
cyclist as she and her aunt wander off to the sidelines.
“Well, well, well…” Someone says from behind them. Dean instinctively turns; his eyes meet with a
pair of deep blue ones staring intently at him, at Y/N, a lopsided grin set onto
the stranger’s face. His hair, a deep onyx, cascades down his neck to his
shoulders. He’s dressed in a suit, very official, very formal, and it makes the
elder Winchester’s stomach turn for a moment.
“Look who it is.” The stranger says.
Dean furrows his brow. “Excuse me?”
His head snaps in the Y/N’s direction, and his confusions swells even
more when he sees the wide grin lacing the young girl’s face.
Her eyes trained on the stranger, she shakes her head slowly. “Oh
“Missed me?” The stranger smirks at her, then goes in for a hug.
Dean steps aside and out of the way, trying not to bump into the
table and almost topples over a tray of croissants. He watches, bewildered, as
the two exchange pleasantries. Y/N’s arms are slung around his neck, as she
giggles then pulls away.
“Very much.” She smiles at him. “Wow. It’s been so long.”
The elder Winchester, attention grasped, looks to her. She points
at the blue-eyed man. “This is Rick—Rick Montoijia! He was my neighbor when I
still lived my parents from, like, two houses down. Uhm, rick, this is my
“Heya.” Rick stretches his hand out for a shake. Hesitating, Dean
eyes it momentarily and then finally accepts the gesture.
“Hi….” His eyes scan the stranger’s face dubiously, his grip firm,
trying to assert dominance. And all of a sudden, something has brewed in his
Something hot and vehement in the space below his ribs; an energy,
a sense of intimidation. It’s stupid to feel, yes, but Dean can’t help it—his
chest floods with a jealousy as he lets go of the other man’s hand.
With an excited smile, Y/N addresses Rick. “What are you doing
here? We—I haven’t seen you in ages.”
“S/P/N’s wedding.” He points to Y/N’s sisters standing a few meters
away. “Obviously I knew you’d be in town for that. I figured,’ well, when was
the last time I saw Y/N L/N?’ and here I am.”
“Here you are.” Dean cuts in.
All eyes shift to him. Y/N peers over Rick’s shoulder, trying to
get a better glimpse, and the green-eyed hunter offers a strained smile; one
far from genuine, something the young girl is obviously familiar with, because
her smile begins to melt away at the sight. Dean doesn’t care. His gaze then
shifts to Rick, whose smile is still smeared across his chiseled face.
“Uhm, yeah…”The dark-haired man laughs nervously. “Here I am.
So…”His attention averts onto Y/N. “How long are you gonna be in town? We need
to catch up.”
“Definitely. I’m here for—“
“—for two weeks. Yeah, we’re here for two weeks.” Y/N finishes,
voice holding a dangerous edge to it. Dean chooses to ignore it, instead
focusing on the way the dark-haired stranger’s face lights up with mirth.
“Wow. That’s great.”
“It really is, Rick. Anyhow, it was great meeting you, but we have
Dean doesn’t give her a chance to object as his hand goes to Y/N’s
waist, and he nudges her forward, quickly trying to get away as fast as
possible. Luckily, they succeed; standing behind them, Rick offers a weak, awkward
goodbye as they move further away. In his chest, dean’s heart thrums rapidly,
His jealousy boils like a hot stew, threatening to spill over, and
he suffocates it; he’s being irrational. He’s being stupid. That guy is just
one of Y/N’s many friends, he reasons. He’s just another familiar face from
Boston, a ghost from her past, nothing too serious…
But the call to worry is stronger than reprimand for Dean.
When she notices his stiffness, Y/N turns to look at the elder
Winchester. Concern swims in her y/e/c eyes. “You okay?”
Attention grasped, Dean turns to her, finds her imploring eyes set
on him. They’re back inside, sitting with Sam and the bride and groom, and the
band is playing some variation of Eric Clapton’s Wonderful Tonight.
Trying to stifle his feelings, the elder Winchester regains
composure, offering a tight-smile. “Oh, yeah.”
“Sure? You seem…absent. Like something’s bothering you.”
“No, nothing’s wrong.” He lets out a sigh. He tries to steady the
quaking in his core, letting his gaze drift across the room. Y/N scoots closer
in and rests her head on his shoulder. Her hair tickles his jaw.
“If you say so…”She says with sigh, her breath fanning against his
skin. Her body is warm against his, like a tepid lava flowing down his skin,
soothing, therapeutic almost.
“Good job back there with nearly killing my dog, by the way. Put
on quite the show.”
The elder Winchester laughs. It’s soft and feint but she can feel
it in the rumble of his body beneath her head.
“Yeah, well, what can I say—I’m a sucker for theatre.”
“Are you now?”
“Oh yeah, massive fan. Plus, anything to get my story told.” Dean
senses it hanging in the air like a string suspended between them, a silent question.
It’s quiet for moment. He then tips his
head to glimpse down at her, a smile playing at his lips.
“I don’t want to.”
“You have to.”
Y/N bites her smile back, a row of her chalky white teeth
contrasting the burgundy on her lips, then lets it all bubble out. “Fine! You
were right. Your good looks and charm won me over—there, are you happy?”
Dean doesn’t bother to try and mask his smile. “Extremely.”
“What’re you guys talking about?”
His head turns; S/P/N waddles over and pulls out a chair a few
seats away, smiling as she sits down. She folds the pleats in her burgundy
“Stuff.” Replies Y/N, head still draped against Dean’s shoulder.
“What kinda stuff?”
“Couple stuff. Dean and Y/N stuff. You wouldn’t understand.” She
smirks; then Dean pokes her side and she lets out a giggle; it’s a sweet, quiet
sound, like the hum of a bird or the wind wisping through the trees, and it makes
the pit in the elder Winchester’s stomach from earlier yawn open.
As Y/N speaks with her sister, the elder Winchester feels a flood
of melancholy coming on. He can always tell when it’s happening; it’s like
watching everything around you happening at a normal pace when all of a sudden
things are slowed down, sluggish, delayed. That’s what Dean feels like right
now. He loathes it.
The evening is electric and dressed in a celebratory energy. More
guests have arrived for the dinner, all pouring in in massive crowds and gaudy
sartorial dresses. Dean has to stand when he greets them all, offering an
amiable smile, the occasional hug and peck as they all fawn—oh my God, the
Dean? Y/N’s Dean?
It gets annoying having to hear everybody so jubilant over meeting
him, at a point. They’re excited to be meeting their sister’s boyfriend, their
niece’s lover, the man whom she, too, shall bring back here to Boston in a few
years to wed. To them, Dean assumes, meeting him is a gateway to another one of
this sartorial dinners just a few years ahead.
To him, it’s plain insulting.
Why did he even agree to this? Playing pretend had seemed less
tedious in his mind. Doing it now, the elder Winchester is wrought with
negative emotions; with jealousies and blind resentments and a bitterness because
he shall have anything but this future with Y/N, and God, is he pissed.
“Dean,” She says, pulling him from his reverie. Aunt Steph and
good ol’ Gary sit across from them, sipping on some champagne and laughing with
Y/N’s parents, and to their left is S/P/N and Japheth. Everyone is laughing and
chatting and the air reeks of jubilance, except for the corner where a heavy
grey cloud hangs over Dean’s head.
Y/N’s hand is on his as he turns to her, her y/e/c eyes trained
intently on his. “What’s wrong?” She pries. He has to say something. Lying
would only act as a catalyst for his negative emotions (lying to Y/N, at least).
So, instead, Dean heaves a heavy breaths and
gathers the feelings in his chest into a single nest.
“Nothing’s wrong.” He says. “I’m just trying to let this all sink
in. Your family. It’s pretty overwhelming meeting all the people in your life
who mean the world to you.”
“I’m sorry if this isn’t how you planned to spend the next two
weeks, Dean.” Y/N’s gaze falters, moving to their hands loosely draped over
Dean’s eyes follow. He shrugs and, taking her hand in his, slowly
links them together absentmindedly. Their fingers fit perfectly, like a key
slipping into a lock, like a tight knot, and he tries to ignore it.
“Don’t be, Y/N.” He replies. “Besides—I’m the one who offered this
in the first place. I don’t really have the luxury of complaining.”
“Should I give it to you?”
When Dean finally looks up, he finds Y/N’s eyes trained on him,
her lips pulled back in pleasant smile. In the background, the music slows to a
stop as it shifts to the next song. More upbeat, more jazzy and fun. The room’s
chatter provides the perfect undertone, but Dean ignores it—all of it, because
all he can focus on right now is Y/N.
His Y/N. For tonight, for two weeks.
He’ll take what he can get, even if it’s having the honor of
playing her boyfriend for a period of time and then going back to being just
her best-friend; to being her Dean and not her
Dean. Going back to a life where she
sees their relationship, although intense, as nothing more than a deep
It’s only been a few hours, but it’s crazy how much can be
revealed to you in such a span of time. Dean sees it now—sees Y/N and, even if
he didn’t think it possible, even more of her than he already has. He sees Y/N
in her element, with her family, with her friends and with a sense of mirth
radiating off her…And as great as it is, all it does for him is nudge at the
thought that he shall never be part of that.
They mean a lot to each other, he knows that much, but today has
made him wonder if he will ever be part of Y/N’s suburban life, whether he’ll
breach past their life spent in the bunker and in pages of lore and into that
which holds this very idyllic essence.
The thought, daunting and unfortunately saddening, hits the elder
Winchester like a ton of bricks. He immediately turns away. He rests his focus
on something—anything—that isn’t Y/N smiling at him and causing an uproar in
the space behind his heart.
The night simmers on, laced with laughter and chatter and smiles
too bright for Dean to bare. He only watches from the sidelines, an observer, a
spectator…Y/N is the center of the orbit that is the eclectic crowd. She
smiles and the entire room responds with an abundance of simpers; her laugh is a
mellifluous symphony overpowering the music, her eyes glint like the stars in
the sky and she throws her head back and captivates the attention of everyone
in the room. She reels them all in like a magnet, like she’s magic…
And to Dean she is…
She always has been and always will be. She is ethereal and glimmering
and inside her is a flame and a tornado and such vehemence that would tear a
mere mortal apart, but doesn’t even scratch her skin the slightest.
Y/N is magic and she will always be magic, and Dean knows this. He
wishes he didn’t, but he does, and it hurts…Because the hollowness in his chest
that comes from watching her so radiant makes him wonder why he said yes to the
torture of being just another planet in her orbit in the first place…
The list is exceedingly long, but what stands out predominantly on
the account of things they were meant to discuss before they left home (but
didn’t), is the sleeping arrangement.
Standing in their hotel bedroom, the elder Winchester stares at
the single bed, at the six fat pillows nested at the head and the vast
comforter definitely two huge for two. It’s a lover’s suit; of course the hotel
would be expecting customer’s to be doing anything but sleeping in these
sheets, but Dean’s case is the exception.
Y/N is in the bathroom getting ready for bed. The sound of the
shower running echoes throughout the otherwise silent room and the elder
Winchester feels a small welt of nervousness claw at his belly. They’ve shared
beds before. This shouldn’t be a big deal…
God, he’s acting like a teenage boy with this. It’s not that hard,
Dean tells himself. They can even divide it into two regions if they want,
Y/N’s, and then the extremely comfy one with the extra pillow for him. They can
sort this out. It doesn’t have to be awkward, eh tries to reason, but something
tugs at his gut and tells him otherwise, because Dean feels all sorts of
Maybe it’s the thought of lying to sleep with her after the
mortal sin they’ve just committed throughout the day: fraud. Artifice. Maybe,
Dean thinks, it’s the fact that they’ll have to pretend to be together even as
they lay to sleep that terrifies him maybe it’s the lover’s suit. He and Y/N
are anything but. All the times they’ve slept in the same bed in the past, it’s
been in dingy, itchy, sketchy motels, not five stars hotels that probably
provide complimentary condoms.
He lifts the thick blanket on the bed and crawls under it, trying
to get comfortable. The bed is cloud, embracing him, engulfing him into its
form like it’s an amoeba and him its prey. God, this is comfy. Dean’s eyes
flutter and he tips his head back in subtle ecstasy.
Right at that moment, the door to the bathroom swings open.
Y/N stomps out in pajama shorts and a towel clasped tightly to her
chest, eyes wide as she glimpses around the room. Opening his eyes, Dean then
ctaches her gaze.
“Sorry.” She apologizes and points to her beg at the foot of the
bed. “I just need my shirt from my suitcase. Don’t look!”
“No promises.” But he doesn’t, instead covering his eyes with one
hand. He hears the patter of feet and the rustling of clothes as Y/N retrieves
the garment, then rushes back into the bathroom. When she returns, a moment later,
this time she’s fully clothed.
“The pressure here is ace.” Y/N says, holding her fingers up in an
appropriate gesture as she saunters towards the bed. She hauls her bag off and
onto the floor, then climbs up, pushing the blanket aside.
“I can’t remember the last time I took a shower and didn’t want to
Dean lowers his hand and looks at her; hair wet and clinging to
her skin, her face is bare, all the makeup from today washed away into the
drain. A few pimples dot the surface of her cheeks and, although feint, there’s
a single splatter of freckles just below her jaw line that Dean always finds
“That’s good to know. In other news: the sleeping arrangement.
How’s this gonna work?”
“You mean top or bottom?”
Y/N’s grin never falters as she laughs. “I don’t really mind,
Dean. If it bothers you, you could always take the floor.”
“I never said it bothers me…”
Her eyes are staring intently into his and he’s trying too damn
hard to not get caught up in them. He shouldn’t. the moment is far from
appropriate. She’s basically telling him to get out of the bed and spend the
night on the floor like a hound, and heaven be damned if Dean is going to let
himself focus on anything but defending himself.
So he tips his head back slightly, locks his eyes on hers, and
says, “Not at all.”
“Then goodnight, Winchester.” Y/N smiles, before turning the
night-light off and wiggling further under the blanket.
Dean mirrors her. He slides beneath it, letting it came up to his
chest and closes his eyes. He can feel the steady beat of his heart, the pulse
of his blood. Sleep hovers over him like a phantom but never once dares to
Minutes pass and he’s still awake. The elder Winchester fidgets,
turning on his side, eyes meeting the bright glare of the moonlight invading
the room. He checks his watch on the bedside table. Two am. Still up. His
eyelids feel heavy and a yawn pries his mouth open, but Dean can’t sleep, and
it’s an insomnia, the worst kind of insomnia, that he’s too familiar with.
He’s dabbled in it in the past; with the mark of cain and in
purgatory. When he was demon, when Sam was soulless and when Cas was presumed dead.
Dean knows this plague, greets it like an old friend, doesn’t even bother
fighting it, but there’s no denying that it’s annoying. He wants rest—needs it.
The last thing he needs right now is a visit from this phantom that keeps him
up, staring at the blank ceiling.
A few seconds subside when silence is broken by hushed voice.
The elder Winchester nods silently. His eyes burn.
“I don’t know.”
“What do you mean you don’t know? You don’t know why you can’t
“That’s what I just said.”
The sheets shift. Y/N props herself up on her elbow, looking at
him, her eyes still swimming with sleep. He wonders what woke her, but remains
silent as he turns to meet her gaze.
Y/N’s eyes are somber and intently set on him; there’s a weight on
her heart for a moment, something that visibly bring out the worry in her gaze.
She’s been with him through all of them; all those times
mentioned, all those calamites in his life, Y/N has walked through them with
Dean. Consequently, she can tell when something’s up. It’s comforting for Dean
to know that’s she’s so in sync with him, that they’ve got this visceral
connection that alerts her when something’s up, but unfortunately now it’s a
bit of a false alarm.
He shakes his head. “No. Just can’t sleep.”
“Oh…” She voices simply and within a moment the solemnity fades.
Then comes the sound of the sheets shifting, Y/N sitting up and she turns on
the nightlight. The warm light right away glares onto the side of his face.
Dean squints, lolling his head to the side.
Y/N’s hair dangles around her face as she looks at him. “Anything
I can do to help? Get a glass of water, sing you a lullaby?”
“Rock me to sleep?” He supplements.
She shrugs. “Anything.”
Then, chuckling, elder Winchester turns away and allows his gaze
to float back to the ceiling. y/N continues to speak in the background, going
on about the day and tomorrow and how everything’s going to go down so that
everything turns out as planned. She’s notified Sam already, apparently. Unlike
Dean, he won’t have to do much besides be himself and distract Marilyn for the
But for Dean, Y/N proclaims, it’s going to be a long two weeks:
he’s going to have to do a lot more than he’d anticipated; more work, more
fraud. For the following days he must wear his disguise as though it is
anything but…and the funny thing? Dean knows it’s going to be elementary…
Because they can only get so much closer.
Because they, before today, already spent nights in bed chatting
about everything and anything that came to mind; because he already used to
walk inches close to her and comb his fingers through her hair and laugh and
feel (God, did he feel), and so maybe this is going to be a walk in the park.
Maybe it will be easy, Dean thinks—until he’s reminded of earlier at dinner and
the gaping hole in his chest.
On 21 August 2017, the Great American Eclipse caused a diagonal swathe of darkness to fall across the United States from Charleston, South Carolina on the East Coast to Lincoln City, Oregon on the West. In Manhattan, which was several hundred miles outside the path of totality, a gentle gloom fell over the city. Yet still office workers emptied out onto the pavements, wearing special paper glasses if they had been organised; holding up their phones and blinking nervously if they hadn’t. Despite promises that it was to be lit up for the occasion, there was no discernible twinkle from the Empire State Building; on Fifth Avenue, the darkened glass façade of Trump Tower grew a little dimmer. In Central Park Zoo, where children and tourists brandished pinhole cameras made from cereal boxes, Betty, a grizzly bear, seized the opportunity to take an unscrutinised dip.
Across the East River in Williamsburg, Brooklyn, Oscar Isaac, a 38-year-old Guatemalan-American actor and one of the profession’s most talented, dynamic and versatile recent prospects, was, like Betty, feeling too much in the sun. It was his day off from playing Hamlet in an acclaimed production at the Public Theater in Manhattan and he was at home on vocal rest. He kept a vague eye on the sky from the balcony of the one-bedroom apartment he shares — until their imminent move to a leafier part of Brooklyn — with his wife, the Danish documentary film-maker Elvira Lind, their Boston Terrier French Bulldog-cross Moby (also called a “Frenchton”, though not by him), and more recently, and to Moby’s initial consternation, their four-month-old son, Eugene.
Plus, he’s seen this kind of thing before. “I was in Guatemala in 1992 when there was a full solar eclipse,” he says the next day, sitting at a table in the restaurant of a fashionably austere hotel near his Williamsburg apartment, dressed in dark T-shirt and jeans and looking — amazingly, given his current theatrical and parental commitments — decidedly fresh. “The animals went crazy; across the whole city you could hear the dogs howling.” Isaac happened to be in Central America, he’ll mention later, because Hurricane Andrew had ripped the roof off the family home in Miami, Florida, while he and his mother, uncle, siblings and cousins huddled inside under couches and cushions. So yes, within the spectrum of Oscar Isaac’s experiences, the Great American Eclipse is no biggie.
Yet there is another upcoming celestial event that will have a reasonably significant impact on Isaac’s life. On 15 December, Star Wars: The Last Jedi will be released in cinemas, which, if you bought a ticket to Star Wars: The Force Awakens — and helped it gross more than $2bn worldwide — you’ll know is a pretty big deal. You’ll also know that Isaac plays Poe Dameron, a hunky, wise-cracking X-wing fighter pilot for the Resistance who became one of the most popular characters of writer-director JJ Abram’s reboot of the franchise thanks to Isaac’s charismatic performance and deadpan delivery (see his “Who talks first?” exchange with Vader-lite baddie Kylo Ren: one of the film’s only comedic beats).
And if you did see Star Wars: The Force Awakens you’ll know that, due to some major father-son conflict, there’s now an opening for a loveable, rogueish, leather-jacket-wearing hero… “Heeeeeh!” says Isaac, Fonzie-style, when I say as much. “Well, there could be, but I think what [The Last Jedi director] Rian [Johnson] did was make it less about filling a slot and more about what the story needs. The fact is now that the Resistance has been whittled to just a handful of people, they’re running for their lives, and Leia is grooming me — him — to be a leader of the Resistance, as opposed to a dashing, rogue hero.”
While he says he has “not that much more, but a little more to do” in this film, he can at least be assured he survives it; he starts filming Episode IX early next year.
If Poe seems like one of the new Star Wars firmament now — alongside John Boyega’s Finn, Daisy Ridley’s Rey and Poe’s spherical robot sidekick BB-8 — it’s only because Isaac willed it. Abrams had originally planned to kill Poe off, but when he met Isaac to discuss him taking the part, Isaac expressed some reservations. “I said that I wasn’t sure because I had already done that role in other movies where you kind of set it up for the main people and then you die spectacularly,” he remembers. “What’s funny is that [producer] Kathleen Kennedy was in the room and she was like, ‘Yeah, you did that for us in Bourne!’” (Sure enough, in 2012’s Bourne Legacy, Jeremy Renner’s character, Aaron Cross, steps out of an Alaskan log cabin while Isaac’s character, Outcome Agent 3, stays inside; a few seconds later the cabin is obliterated by a missile fired from a passing drone.)
This ability to back himself — judiciously and, one can imagine after meeting him, with no small amount of steely charm — seems to have served Isaac well so far. It’s what also saw him through the casting process for his breakthrough role in Joel and Ethan Coen’s 2014 film Inside Llewyn Davis, about a struggling folk singer in Sixties New York, partly based on the memoir of nearly-was musician Dave Van Ronk. Isaac, an accomplished musician himself, got wind that the Coens were casting and pestered his agent and manager to send over a tape, eventually landing himself an audition.
“I knew it was based on Dave Van Ronk and I looked nothing like him,” says Isaac. “He was a 6ft 5in, 300lb Swede and I was coming in there like… ‘Oh man.’” But then he noticed that the casting execs had with them a picture of the singer-songwriter Ray LaMontagne. “Suddenly, I got some confidence because he’s small and dark so I said to the casting director, ‘Oh cool, is that a reference?’ And they were like, ‘No, he just came in here and he killed it.’” Isaac throws his head back and laughs. “They literally said, 'He killed it.’ It was so good!”
In the end it was Isaac who killed it in Inside Llewyn Davis, with a performance that was funny, sad, cantankerous and moving. The film was nominated for two Oscars and three Golden Globes, one of them for Isaac in the category of: “Best Performance by an Actor in a Motion Picture — comedy or musical” (he lost to Leonardo DiCaprio for The Wolf of Wall Street). No cigar that time, but in 2016 he won a Golden Globe for his turn as a doomed mayor in David Simon’s HBO drama, Show Me a Hero. This year, and with peculiar hillbilly affectation, Vanity Fair proclaimed Isaac “the best dang actor of his generation”. It is not much of a stretch to imagine that, some day very soon, Isaac may become the first Oscar since Hammerstein to win the award whose name he shares. Certainly, the stars seem ready to align.
Of course, life stories do not run as neatly as all that and Isaac’s could have gone quite differently. He was born Óscar Isaac Hernández Estrada in Guatemala City, to which his father, Óscar, now a pulmonologist, had moved from Washington DC in order to attend medical school (having escaped to the States from Cuba just before the revolution) and where he met Isaac’s mother, Eugenia. Five months after Isaac was born, the family — also including an older sister, Nicole, and later joined by a younger brother, Michael — moved to America in order for Óscar Senior to complete his residencies: first to Baltimore, then New Orleans, eventually settling in Miami when Isaac was six.
Miami didn’t sit entirely right with him. “The Latin culture is so strong which was really nice,” he says, “but you had to drive everywhere, and it’s also strangely quite conservative. Money is valued, and nice cars and clothes, and what you look like, and that can get sort of tedious.” Still it was there, aged 11, that he took to the stage for the first time. The Christian middle school he attended put on performances in which the kids would mime to songs telling loosely biblical stories, including one in which Jesus and the Devil take part in a boxing match in heaven (note the word “loosely”). For that one, Isaac played the Devil. In another, he played Jesus calling Lazarus from the grave. “So yeah,” he laughs, “I’ve got the full range!’
He enjoyed the mixture of the attention and the “extreme nature of putting yourself out there in front of a bunch of people”, plus it gave him some release from stresses at home: his parents were separating and his mother became ill. His school failed to see these as sufficiently mitigating factors for Isaac’s subsequent wayward behaviour and, following an incident with a fire extinguisher, he was expelled. “It wasn’t that bad. They wanted me out of there. I was very happy to go.”
Following his parents’ divorce, he moved with his mother to Palm Beach, Florida, where he enrolled at a public high school. “It was glorious, I loved it,” says Isaac. “I loved it so much. I could walk to the beach every day, and go to this wild school where I became friends with so many different kinds of people. I met these guys who lived in the trailer parks in Boynton Beach and started a band, and my mom and my little brother would come and spy on me to see if I was doing drugs or anything, and I never was.”
“No, because I didn’t drink till I was, like, 24. Even though I stopped being religious, I liked the individuality of being the guy who didn’t do that stuff. Maybe it was the observer part of me… I liked being a little bit detached, and I wasn’t interested in doing something that was going to make me lose control.”
When he was 14, Isaac and his band-mates played at a talent show. They chose to perform 'Rape Me’ by Nirvana. “I remember singing to the parents, 'Rape meeee!’” Isaac laughs so hard he gives a little snort. “Yeah,” he says, composing himself again, “we didn’t win.” But something stuck and Isaac ended up being in a series of ska-punk outfits, first Paperface, then The Worms and later The Blinking Underdogs who, legend has it, would go on to support Green Day. “Supported… Ha! It was a festival…” says Isaac. “But hey, we played the same day, at the same festival, within a few hours of each other.” (On YouTube you can find a clip from 2001 of The Blinking Underdogs performing in a battle of the bands contest at somewhere called Spanky’s. Isaac is wearing a 'New York City’ T-shirt and brandishing a wine-coloured Flying V electric guitar.)
Still, Isaac’s path was uncertain. At one point he thought about joining the Marines. “The sax player in my band had grown up in a military family so we were like, 'Hey, let’s work out and get all ripped and be badasses!’” he says. “I was like, 'Yeah, I’ll do combat photography!’ My dad was really against it. He said, 'Clinton’s just going to make up a war for you guys to go to,’ so I had to have the recruiters come all the way down to Miami where my dad was living and they convinced him to let me join. I did the exam, I took the oath, but then we had gotten the money together to record an album with The Worms. I decided I’d join the Reserves instead. I said I wanted to do combat photography. They said, 'We don’t do that in the Reserves, but we can give you anti-tank?’ Ha! I was like, 'it’s a liiiiiittle different to what I was thinking…’”
Even when he started doing a few professional theatre gigs in Miami he was still toying with the idea of a music career, until one day, while in New York playing a young Fidel Castro in an off-Broadway production of Rogelio Martinez’s play, When it’s Cocktail Time in Cuba, he happened to pass by renowned performing arts school Juilliard. On a whim, he asked for an audition. He was told the deadline had passed. He insisted. They gave him a form. He filled it in and brought it back the next day. They post-dated it. He got in. And the rest is history. Only it wasn’t.
“In the second year they would do cuts,” Isaac says. “If you don’t do better they kick you out. All the acting teachers wanted me on probation, because they didn’t think I was trying hard enough.” Not for the first or last time, he held his ground. “It was just to spur me to do better I think, but I definitely argued.”
He stayed for the full course at Juilliard, though it was a challenge, not only because he’d relaxed his own non-drinking rule but also because he was maintaining a long-distance relationship with a girlfriend back in Florida. “For me, the twenties were the more difficult part of life. Four years is just… masochistic. We were a particularly close group but still, it’s really intense.” (Among his fellow students at the time were the actress Jessica Chastain, with whom he starred in the 2014 mob drama A Most Violent Year, and Sam Gold, his director in Hamlet.) He says he broadly kept it together: “I was never a mess, I just had a lot of confusion.” He got himself an agent in the graduation scrum, and soon started picking up work: a Law & Order here, a Shakespeare in the Park there; even, in 2006, a biblical story to rival his early efforts, playing Joseph in The Nativity Story (the first film to hold its premiere at the Vatican, no less).
By the time he enrolled at Juilliard he had already dropped “Hernández” and started going by Oscar Isaac, his two first given names. And for good reason. “When I was in Miami, there were a couple of other Oscar Hernándezes I would see at auditions. All [casting directors] would see me for was 'the gangster’ or whatever, so I was like, 'Well, let me see if this helps.’ I remember there was a casting director down there because [Men in Black director] Barry Sonnenfeld was doing a movie; she said, 'Let’s bring in this Oscar Isaac,’ and he was like, 'No no no! I just want Cubans!’ I saw Barry Sonnenfeld a couple of years ago and I told him that story — 'I don’t want a Jew, I want a Cuban!’”
Perhaps it’s a sad indictment of the entertainment industry that a Latino actor can’t expect a fair run at parts without erasing some of the ethnic signifiers in his own name, but on a personal basis at least, Isaac’s diverse role roster speaks to the canniness of his decision. He has played an English king in Ridley Scott’s Robin Hood(2010), a Russian security guard in Madonna’s Edward-and-Mrs-Simpson drama W.E. (2011), an Armenian medical student in Terry George’s The Promise (2017) and — yes, Barry — a small, dark American Jew channelling a large blond Swede.
But then, of course, there are roles he’s played where ethnicity was all but irrelevant and talent was everything. Carey Mulligan’s ex-con husband Standard in Nicolas Winding Refn’s Drive in 2011 (another contender for his “spectacular deaths” series); mysterious technocrat Nathan Bateman in the beautifully poised sci-fi Ex Machina (2014) written and directed by Alex Garland (with whom he has also shot Annihilation — dashing between different sound stages at Pinewood while shooting The Last Jedi — which is due out next year). Or this month’s Suburbicon, a neat black comedy directed by George Clooney from an ancient Coen brothers script, in which Isaac cameos as a claims investigator looking into some dodgy paperwork filed by Julianne Moore and Matt Damon, and lights up every one of his brief scenes.
Isaac is a very modern kind of actor: one who shows range and versatility without being bland; who is handsome with his dark, intense eyes, heavy brows and thick curls, but not so freakishly handsome that it is distracting; who shows a casual disregard for the significance of celebrity and keeps his family, including his father, who remarried and had another son and daughter, close. It’s a testament to his skill that when he takes on a character, be it English royal or Greenwich Village pauper, it feels like — with the possible exception of Ray LaMontagne — it could never have been anyone else.
Today, though, he’s a Danish prince. To say that Isaac’s turn in Hamlet has caused a frenzy in New York would be something of an understatement. Certainly, it’s a sell-out. The Sunday before we meet, Al Pacino had been in. So scarce are tickets that Isaac’s own publicist says she’s unlikely to be able to get me one, and as soon as our interview is over I hightail it to the Public Theater to queue up to be put on the waiting list for returns for tonight’s performance. (I am seventh in line, and in my shameless desperation I tell the woman in front of me that I’ve flown over from London just to interview Isaac in the hope that she might let me jump the queue. She ponders it for a nanosecond, before another woman behind me starts talking about how her day job involves painting pictures of chimpanzees, and I lose the crowd.)
Clearly, Hamlet is occupying a great deal of Isaac’s available brain space right now, and not just the fact that he’s had to memorise approximately 1,500 lines. “Even tonight it’s different, what the play means to me,” he says. “It’s almost like a religious text, because it has the ambiguity of the Bible where you can look at one line and it can mean so many different things depending on how you meditate on it. Even when I have a night where I feel not particularly connected emotionally, it can still teach me. I’ll say a line and I’ll say, 'Ah, that’s good advice, Shakespeare, thank you.’”
Hamlet resonates with Isaac for reasons that he would never have foreseen or have wished for. While playing a young man mourning the untimely death of his father, Isaac was himself a young man mourning the untimely death of his mother, who died in February after an illness. Doing the play became a way to process his loss.
“It’s almost like this is the only framework where you can give expression to such intense emotions. Otherwise anywhere else is pretty inappropriate, unless you’re just in a room screaming to yourself,” he says. “This play is a beautiful morality tale about how to get through grief; to experience it every night for the last four months has definitely been cathartic but also educational; it has given structure to something that felt so overwhelming.”
In March, a month after Eugenia died, Isaac and Lind married, and then in April Eugene, named in remembrance of his late grandmother, was born. I ask Isaac about the shift in perspective that happens when you become a parent; whether he felt his own focus switch from being a son to being a father.
“It happened in a very dramatic way,” he says. “In a matter of three months my mother passed and my son was born, so that transition was very alive, to the point where I was telling my mom, 'I think you’re going to see him on the way out, tell him to listen to me as much as he can…’” He gives another laugh, but flat this time. “It was really tough because for me she was the only true example of unconditional love. It’s painful to know that that won’t exist for me anymore, other than me giving it to him. So now this isn’t happening” — he raises his arms towards the ceiling, gesturing a flow coming down towards him — “but now it goes this way” — he brings his arms down, making the same gesture, but flowing from him to the floor.
Does performing Hamlet, however pertinent its themes, ever feel like a way of refracting his own experiences, rather than feeling them in their rawest form?
“Yeah it is,” he says, “I’m sure when it’s over I don’t know how those things will live.” He pauses. “I’m a little bit… I don’t know if 'concerned’ is the right word, but as there’s only two weeks left of doing it, I’m curious to see what’s on the other end, when there’s no place to put it all.”
It’s a thoughtful, honest answer; one that doesn’t shy away from the emotional complexities of what he’s experiencing and is still to face, but admits to his own ignorance of what comes next. Because, although Isaac is clearly dedicated to his current lot, he has also suffered enough slings and arrows to know where self-determination has its limits.
What he does know is happening on the other end of Hamlet is “disconnection”, also known as a holiday, and he plans to travel with Lind to Maine where her documentary, Bobbi Jene, is screening at a film festival. Then he will fly to Buenos Aires for a couple of months filming Operation Finale, a drama about the 1960 Israeli capture of Adolf Eichmann which Isaac is producing and in which he also stars as Mossad agent Peter Malkin, with Eichmann played by Sir Ben Kingsley. At some point after that he will get sucked into the vortex of promotion for Star Wars: The Last Jedi, of which today’s interview is an early glimmer.
But before that, he will unlock the immaculate black bicycle that he had chained up outside the hotel and disappear back into Brooklyn. Later, he will take the subway to Manhattan an hour-and-a-half or so before curtain. To get himself ready, and if the mood takes him, he will listen to Venezuelan musician Arca’s self-titled album or Sufjan Stevens’ Carrie and Lowell, light a candle, and look at a picture of his mother that he keeps in his dressing room.
Then, just before seven o'clock, he will make his way to the stage where, for the next four hours, he will make the packed house believe he is thinking Hamlet’s thoughts for the very first time, and strut around in his underpants feigning madness, and — for reasons that make a lot more sense if you’re there which, thanks to a last-minute phone-call from the office of someone whose name I never did catch, I was — stab a lasagna. And then at the end of Act V, when Hamlet lies dead, and as lightning staggers across the night sky outside the theatre, finally bringing the promised drama to the Manhattan skyline, the audience, as one, will rise.
Fashion by Allan Kennedy. Star Wars: The Last Jedi is out on 15 December. The December issue of Esquire is out now.
Fike cigaren mbi doren time? -Cfare? -Fike cigaren te dora ime. Dua te me mbese nje shenje nga ti. -Mos u cmende gje? Te dhemb. -Jo, ta them un cfare dhemb. Dhemb te presesh nje mesazh cdo dite, qe nuk vjen kurre. Ti fiksosh syte per ore te tera te celulari qe nuk bie. Dhemb te shkoj te fle duke menduar se cfare do jesh duke bere ti. Dhemb kur mendoj qe mund te flasesh me nje vajze tjeter, qe eshte me e bukur se une. Dhemb kur di qe s'do jesh me mua gjithmone. Do me dhembi e do me beje keq me shume kur te jete ftohte dhe nuk do mund te te perqafoj, kur te jem e lumtur dhe nuk mund te ta them arsyen pse, kur te kem nevoj te rri me ty dhe atehere mes lotesh do filloj te shoh fotografite tona. Do me beje keq edhe kur ne nje nate vere te shoh qiellin plot me yje dhe do me duket sikur te kam prane meje. E di, e di qe me ke bere keq dhe do vazhdosh te me besh akoma, prandaj fike ate cigare mbi doren time sepse dua te te kujtoj gjithmone, qe pavarsisht gjithe dhimbjes qe ndjej, une te kam dashur, te dua. Pavarsisht gjithckaje.. ja vlejte Zemer. ..
Request: request for a John imagine where you don’t quite realise how dangerous he is bc you haven’t been dating that long until your walking back from the shops one day and you see him beating up a guy because he said some bad shit about you and u run away cos ur scared but then John finds u and comforts you. Thank u X
Request: Can I ask one with John where he get jealous when someone flirt with reader? Something like really jealous ahahhah I love your fics you are amazing at writing 😍😍😍 - @buckybear-ivar
Dangerous - John Shelby
You had moved to Small Heath from Newcastle two months ago when your grandfather wrote to your mother to tell her that he was sick. He had left his dowry, which he had accumulated after years of work and saving, to you (his only grandchild) and your father felt it was important that you go down to be with him in his last months as repayment for his generosity. So you had packed a few belongings and travelled down to Small Heath.
There were a few things that your grandfather was eager to tell you about Small Heath when you first arrived. It was his home and he was proud of it but he cautioned you against some of the neighbors. The Shelbys, according to your father, were devils. He told you to stay as far from the Shelby family as you possibly could but, if you were to see them, be polite.
“Are they really that bad?” You’d laughed at the stories your grandfather told you.