I Love You, Still
Pairings: Dean x reader & (kind of) Chuck Bass x reader
Warnings: None that I’m aware of.
Summary: You live in the Upper East Side of New York and run into your high school sweetheart, Dean who you haven’t seen in years.
A/N: This is a cross-over between Gossip Girl and Supernatural that I’ve been wanting to write this for a while, you don’t need to know anything about Gossip Girl and there won’t be any spoilers (if there are I’ll put it in the warning) I hope you guys enjoy it, this part was a little bland due to its just the beginning. Feedback on if you want me to continue this series would be much appreciated!
Hundreds of people chat amongst you, none of which speak to you. Elegant people sway together in tune with the quiet orchestra, snobby women boss around waiters and rich men smoke cigars and gloat about their new investments.
You watch them from your corner, isolated from their world. No matter how many times you practiced walking in your heels, or how many galas you attended, or how much you spent on fine dresses, you felt as if you’d never fit in. This wasn’t your world, it was merely an extended vacation you’d spend an eternity in, the luxury life was enchanting, but you still yearn for something more.
With a sigh you set your champagne glass down causing the crystal to sing when it hits the table, you pinch your golden gown and raise your dress to maneuver around fellow guests, your stilettos click against the hardwood beneath you as you make your way towards the exit.
You squeeze through laughing bodies and ignore catcalls from drunk men, wanting to be as far away as possible. Without warning, a body slams against you, you murmur hushed apologies to the stranger while trying to regain your balance.
“Y/N?” you lock with the green orbs you haven’t seen in years.
“Dean?” your voice was barely audible, in awe at the gorgeous man in front of you. You open your mouth to speak but no words could form, he seems just as surprised as you, his eyes wander all over your body taking in your appearance. “I was just about to go get some fresh air,” your voice gets lost somewhere in the background noise, but he heard you clearly, “Would you like to join me?” you invite, he nods in response following you out of the crowded room.
The air nips at your arms when the both of you step into the night and out of the noise, Dean shrugs off his suit jacket and sets the fabric around your shoulders, you give him a hushed ‘thank you’ not denying the warmth. “There’s a diner not too far from here, would you like dinner?” Dean shoves his hands into his pockets to keep them from the chilly air, you suddenly feel guilty for taking his jacket.
“Dinner sounds great.” the walk to the diner was filled with an awkward silence neither of you knew how to break. Car horns wail into the night, voices fill the air, and loud music pools out of open windows and into the wind. You pass rows of sleeping houses and busy night clubs, you were surrounded by pavement and it felt as if either of you weren’t allowed to leave.
A bell chimes as you enter the diner, a familiar smile greets you when you step into the dimly lit building. “Y/N, it’s great to see you again!” a plump woman jabbers behind the counter.
“Hello, Maria, it’s as if you didn’t see me just last week.” Maria hobbles over to the menus and leads you two towards your usual spot.
“I never seat anyone here but my favorite customer,” Maria whispers to Dean and shoots you a wink before making her way back to the front of her restaurant.
“I come here a lot,” you explain seating yourself from across Dean, “To get away from the noise, to feel like I’m at home again.” You open your menu as Dean situates himself. “So tell me, Mr. Winchester,” you look up already knowing what you’re going to order, “What brings you to the Upper East Side of New York?”
“I’m working on a case, I’m a detective.” he explains placing his menu to the side, ready to order.
“Oh really? That sounds interesting, do you travel a lot for your job or are you usually in one place?” you question.
“I’ve traveled all over the country, but usually they keep me local back in Lawrence.” just the sound of your hometown made your heart ache. Maria appears handing you both waters and quickly scribbling down Dean’s order, not bothering to ask you what you wanted, for she already knew the answer. “You’re married?” Dean’s voice falters, your eyes follow his stare, right to your hand exposing an exquisite diamond. Disappointment buries in your stomach, suddenly wishing Dean never saw the jewel.
“Engaged,” you admit, not daring to meet his eyes.
“He’s a lucky man.” a thick silence covered you both, this time only momentarily. “Well, what’s new besides that you’re a bride-to-be?” you clear the awkwardness out of your throat, excited to tell him what you’ve accomplished in the past few years.
“I graduated from Yale like I planned, I got my masters in English. At the end of senior year, I published one of my books and it became a bestseller and now I’m here.” your hand motions around the nearly empty room referencing New York. “I met Chuck shortly after I moved here and everything worked out I suppose.” you look down at the ring he gave you, you couldn’t even muster a smile.
“Are you happy?” he inquired,
“Excuse me?” your head leans to the side, not understanding his question.
“Are you happy?” his question hits somewhere deep inside you, it breaks open a wall you’ve glued shut ever since you arrived in the Upper East Side of New York. You always assumed you were, how couldn’t you be? You have an abundance of money, an extremely successful job, a gorgeous home, a fiancé who’s been nothing but great towards you. What was missing?
“I don’t know.” you admit, “I feel like I just need a break, I need to get away from New York and work. I want to feel like a person again.” Dean nods along as you ramble on.
“I’m going back to Lawrence tomorrow morning, why don’t you come back with me and spend a week or so there and come back?” he offers.
“I think I need that,” you nod at his idea, opening up a new conversation, already tired of hearing about yourself.
Over the course of the meal you learn about everything you’ve missed over the past years, Sam recently got engaged to a beautiful girl Jess, Dean raves about how perfect she is for his little brother. He mentions John and Mary’s wedding anniversary is the coming weekend and couldn’t wait for them to see you again. The night was filled with long conversations and bad jokes as if nothing had changed since high school, you almost forgot it had.
You were the last couple to stumble out of Maria’s diner, your laughter fills the chilly air around you, Dean shares stories of past cases you couldn’t believe to be true and you rave about crazy frat parties you used to attend, the awkwardness evaporates with each passing laugh and each passing story.
The dreaded moment came all too soon, you find yourself standing outside of the apartment building you call home, the laughter subsides and frowns curl on both of your lips. Dean clears his throat and pushes the large glass door open for you. The lobby air was warm against your skin, the only sound arises from the fountain in the center of the large room. Dean’s eyebrows raise at the luxury space he stands in, unacquainted with the normalities of the Upper East Side.
“I guess this is goodbye until morning.” You turn to the boy you once loved, for a moment he looks the same, you see the same cheekbones and the same smile, you still get captivated by the brilliance of his green eyes. “This is yours,” you remove his jacket exposing your bare arms once again.
“I’ll meet you here tomorrow morning, we’ll grab coffee or something before we head to the airport.” Dean explains taking his jacket from you, “You looked stunning tonight, as always.” he leans close to your ear, placing a quick kiss to your cheek before turning out of the building and back to wherever he’s staying for the evening.
You step out of the elevator door and into your home sneaking in as quietly as you could, your dress drags behind you as you step out of your heels and onto the tile. You maneuver in the darkness not wanting to wake your sleeping groom as you make your way into the bathroom. You tear off the expensive fabric and toss it to the side of the large space, you rip out hair accessories, and scrub your face free of makeup until it feels almost raw. You stare at the girl you once knew but only a stranger stands before you, you search for the girl you once were and for a moment you swear you found her, but she’s gone as soon as she came, she leaves you feeling more alone than before.
You slip into a nightgown and into the sheets beside Chuck who stirs awake at your sudden presence. “There you are, where have you been?” his voice croaks, his throat unfamiliar with his voice.
“I needed to get some air.” you lie, pulling the sheets over the both of you, “I’m having major writer’s block and need to escape New York for the week, I’m flying to Paris tomorrow morning.” his arms snake around you, pulling your body closer to his own.
“Okay darling, anything for you.” he kisses your ear softly before falling back into a deep slumber. You stare into the darkness aching for sleep that refuses to come, your phone buzzes on the night table, illuminating the bedroom with light.
“Tonight was great, see you tomorrow. -D”
You smile at his simple words remembering the late night conversations you would have often with the same man so long ago. Your eyes flutter slowly and soon you drift off into a deep sleep thinking about the boy you’ve never stopped loving.