When Gabrielle Milton was 8 years old, she attended her first wedding.
Her cousin Anna was getting married and the event was the most glorious thing she ever experienced in her entire life: the dresses, the decorations, the dancing, the cake. Gabrielle had never seen anything as amazing as a wedding in her entire life. That evening as her parents drove her home, the bouquet she'd caught clutched tightly in her lap, she decided that she wanted a wedding just like that one. From that day forward, it became her mission.
Over the following years, Gabby filled notebook after notebook with sketches, clippings from magazines like "Bride" and "The Knot", and photographs of destinations that would make for a perfect honeymoon. Her parents thought it was adorable, a little girl planning her dream wedding, but they assumed that eventually something else would grab their daughter's typically highly-unfocused attention.
It never did, though. Well into her teens, Gabby was still carrying around wedding magazines in her backpack, scouring them with any spare time she had. The walls of her room were covered in pinned images of happy couples and women in ethereal white gowns looking virginal and demure.
If anyone ever found out about Gabby's interest, they were quick to ask who the lucky man was going to be. It always came as a surprise when Gabby declared, very firmly, that she didn't like boys. Like, at all.
It was an even greater surprise when Gabby revealed to her parents one evening, sometime in her sophomore year of college, that she wasn't sure she she even wanted to get married anymore.
Her parents, while constantly supportive of their daughter, were confused as to what caused this shift.
Most of the blame fell on the couples she saw around her. While her parents had a solid marriage, Gabby felt disillusioned by the large number of people that seemed to get married for, what she felt, were the wrong reasons. So many of her parents' friends and family married someone because they were getting on in years or because they felt obligated after such a long time together.
Even her cousin Anna, whose first wedding set off Gabby's love, seemed to float in and out of relationships and marriages like they were fashion trends. It made Gabby sad to see people equating comfort and love as mutually exclusive.
In spite of her new vow of celibacy, Gabriel found a way to put a positive spin on it: Wedding Planning. Years of obsessing over wedding magazines and bridal shops had given her an in-depth knowledge of the business.
Her first client was her cousin Anna, getting married for the fourth time.
Gabby enjoyed planning other people's weddings much more than she ever did imagining her own. She got to be part of this wonderful and romantic event without the hassle of real world stress or problems.
For Gabrielle, she only ever saw her clients living happily ever after.
23 years later
Gabby breezes into her office on Monday morning, two cups of coffee and a white paper bag in hand. Her business partner Castiel sits at his desk, barely looking up from his laptop as she sweeps by.
"Hey there, Castiel," she offers.
"You're late," Cas mutters.
"Office hours don't begin until 9 a.m. It's only 8:52.," Gabby counters. "That's not even close to late." Cas shakes his head.
"'7 Habits' says to be proactive. Being early is part of that," Cas says. Gabby smirks and stands in front of his desk, setting the bag down and placing a hand on her hip.
"Funny, I thought I was the one in charge here?" Gabby asks sardonically. "I mean is does say 'Milton Weddings and Events' on the door, right? Last I checked, you were a Novak."
"A Novak-Milton," Castiel corrects. "And it's a fifty-fifty split."
"Was my business first," Gabby says, setting both drinks down and removing her coat. "If it weren't for me, you'd still be at that horrible accounting firm, playing Cones of Dunshire or whatever."
"It was Magic the Gathering and it was one time," Castiel sighs in aggravation and swipes a hand over his face. "God, I hate you sometime."
"You love me," Gabby insists.
"I love you because you're my cousin," he clarifies. "I don't have a choice."
"No, you love me because you love me." She picks up the paper bag and one of the cups. "I brought you a dirty chai and a honey bun," she sing-songs. Castiel's shoulders slump and he looks up longingly at the food. He takes the items and mumbles a 'thank you' before reaching into the bag. He takes a hearty bite out of the roll, moaning in pleasure.
Gabby carefully sips her coffee, affectionately rolling her eyes at the display.
"You should start trying to show up earlier," Castiel suggests, swallowing down a bite. "It's good business practices."
"I like my sleep," she argues. "Keeps me sharp, organized." Cas glances at the disheveled state of Gabby's side of the office in comparison to his own.
"Your desk says otherwise," he mutters with a small smirk.
"Shut up and drink your tea," she chuckles, pulling off the lid of her drink and scooping up a finger-full of whip cream. She opens her email, clicking through it and deleting the junk.
"The Turner Wedding needs to be postponed," Cas says, reading an email. "I guess the fiancé and Mr. Turner got into a fistfight this weekend." Gabby rolls her eyes.
"I had to call in every favor under the sun to secure that hall. There's is no way I'm cancelling it just because of a little fight with the Father-of-the-Bride," Gabby huffs, licking a bit of cream from the corner of her mouth. "Just give them a week to cool off, remind Mr. Turner of how much money he's already spent, and how non-refundable it all is. I'm sure he'll make an effort to act nice with his future son-in-law." Castiel nods and types out a reply.
"Also," he says, "we have a meeting with a potential client this morning."
Gabrielle nearly chokes on her macchiato.
"Castiel, what are you doing?" She asks, "Mondays are about regrouping, recollecting, getting feedback… We don't do client meetings on Mondays."
"She was insistent," Cas says, rising from his chair and grabbing a thin folder off his desk. He opens it and begins to read. "Miss Samantha Winchester. Wedding in six months."
"Six months!?" Gabby scoffs incredulously. "Cas, it's hard enough planning a wedding in a year! We're not miracle workers. We can't just…" She waves her hand in the air. "Conjure up choice venues."
Cas quirks his mouth to the side and drops the client profile sheet onto Gabby's desk. "She offered to pay a $10,000 deposit to start." Gabby's eyes go wide and her jaw drops open.
"Are you serious?" She mutters. Cas nods and smiles.
"And she said, I quote, 'Money is no object,'" Cas continues. Gabby narrows her gaze doubtfully and picks up the profile sheet. It's just a simple introduction sheet Gabby gives most brides asking them about things like vacation destinations, hobbies, favorite colors and other pertinent information. Samantha's sheet is sparsely filled out, only including name and birthdate.
"And she's coming by today?" Gabby asks. Cas pulls up his sleeve and glances at his watch.
"10 am, actually," he says. Gabby sighs heavily.
"That's not enough time to pull out all of the sample books," Gabby mumbles to herself. "Do you have a blank "Bride Binder" ready?"
"Not yet, but give me a few," Cas says, moving back to his desk. Gabby turns her attention to the shelf behind her desk. She grabs a blank notebook planner, flipping through it absently.
"I hope she means it when she says money is no object," she mutters. She grabs a sharpie from her pen holder and scrawls "S. Winchester" across the front of the notebook.
10 a.m. arrives, as does Samantha Winchester.
"Hello?" A soft, hesitant voice calls out from the small waiting area. Gabby rises to her feet, smooths down her dress shirt and slacks, and walks out front.
She stops dead in her tracks as soon as she sees her.
A tall, lanky brunette in a pair of skinny jeans and a J. Crew sweater stands awkwardly in the center of the room. Gabby slows her stride as she enters, struck by how lovely this woman is. Her cheekbones are high and elegant and her pale hazel eyes are shy and thoughtful.
"Can I, uh, help you?" Gabby says, finally finding her voice. The woman turns to face her, smiling brightly.
"Hi, I'm Samantha Winchester," she offers her hand in Gabby's direction, "I have an appointment today."
"Of course," Gabby replies, looking up at her and cursing her own short stature. "Gabrielle Milton. It's very nice to meet you. Why don't we move back to the office and we can start discussing you-"
"Sami?" A rough voice calls out as a short, dirty blonde head pokes through the door. A tall, bow-legged body follows as who Gabby can only assume is the fiancé strides into the waiting room. Gabby feels like it's the invasion of the pretty people: first the Victoria's Secret Angel and now the guy who looks like he stepped off of Calvin Klein Billboard.
"You must be the fiancé," Gabby steps forward, taking the man's hand in hers and shaking it roughly. "Very nice to meet you and your bride-to-be here. You are a very handsome man, has anyone ever told you that?" Gabby glances between the two of them.
"You two… are going to have some ridiculously attractive children. You have a great genetic combo going on here. Trust me, I deal with couples all the time and I can honestly say that it's very uncommon for partners to be on equal footing, face-wise." Samantha and the man both give each other confused looks and glance back at Gabby.
"Uh… this is my brother Dean, actually." Samantha says, "My fiancé Luke is on a business trip this week."
"Yeah, we're not hooking up. That's, uh… No," Dean says, swinging a finger between himself and Samantha. "I'm just here to help out Sami, make sure she gets what she wants." Gabby catches a flicker of irritation across Samantha's face as he says and notes that this is most likely a hot button between the two of them.
"Why don't we move back to my office and we can start discussing your wedding plans?" Gabby offers, directing the two of them down the hall.
"Dean, Samantha, this is my business partner Castiel Novak," she introduces. Castiel half rises from his desk as they enter, shaking their hands. Gabby directs them to a pair of chairs in front of her desk. "Take a seat." Gabby sits halfway on the corner of her desk and casually crosses her arms.
"So Samantha," she begins. "First we're going to play a little word association. What word do you want people to associate with your wedding?" Samantha blinks several times and opens her mouth but doesn't speak. She bites at her lip as she thinks.
"Well," she says, "I guess… elegant? Yeah, elegant works. I mean, obviously a church-" Dean scoffs loudly.
"Really, Sam," he mutters. "A church? We're not even religious." Samantha glares at Dean
"It's traditional," she argues, turning back to Gabby, "And right now the guestlist is at about 500 people-"
"500?!" Dean gapes. "Last time you said 200, max."
"Well, Luke pointed out that the London office-"
"Oh, here we go," Dean throws his hands up in the air. "I don't understand this guy. He drags his heels for months on setting a date, keeping you on ice, and now all of a sudden he has to have his input?" Samantha's nostrils flare and she looks like she's about to lay into her brother.
"It's his wedding, too," she insists, "and you have no right to start dictating what I want."
"What happened to 'little ceremony at the Botanical Garden,'" Dean's voice rises, "Or a 'Weekend in Vegas?'"
"Dean, quit trying to make all of the decisions! This is not your wedding! It's mine!"
"Then act like it, Sami! Don't just do what Luke wants!"
"Oooookay, you two," Gabby says, holding out her hands to quiet them. "Let's take this down a notch, alright? Clearly, there is a lot of emotion surrounding all of this. Nothing Cas or I haven't dealt with before. Hey Cas?" She shouts over her shoulder, getting his attention.
"Why don't you and Dean all grab us a cup of coffee, maybe something sweet, and we'll clear the air a little bit." Dean narrows his gaze as Castiel tugs on the sleeve of his jacket.
"It's like she's trying to get rid of me," he mutters.
"Not trying. Doing," Cas sighs, pulling Dean out the door. Gabby watches them leave before turning her attention back to Samantha.
"What's up, hun?" she asks. Samantha sighs heavily and runs her fingers through her hair, pulling at the long strands.
"He hates my fiancé," she admits.
"Evidently," Gabby says with a snort. "But why exactly?" Samantha looks away, idly picking at her bitten fingernails.
"He thinks Luke is a controlling asshole," she replies quietly. "Which is kind of ironic because Dean himself is a controlling asshole." Gabby nods in understanding.
"Older brother?" she asks. Samantha nods.
"Yeah, but times like this he acts more like a dad," She shakes her head and laughs humorlessly, "Even though we actually have a dad." Gabby moves into Dean's vacated seat and considers Samantha.
"Was he right, though? Is this something you don't actually want?" Gabby asks, "I mean the big wedding, not just the wedding in general." Samantha bites at her lip before shrugging slightly and nodding.
"I guess, it's just…" She slouches back into the chair and groans, "I know Luke would want his whole firm their and his family is huge, I just... I just don't think he'd be happy with a small, private thing." Gabby sits up straight and crosses her arms, mind whirring as she considers this. She's seen brides like Samantha before; girls who are so self-sacrificing that they have a hard time admitting what they really want, even when they know what it is.
"Well, did Luke ever say he'd be unhappy with a small gathering?" Gabby asks carefully. Samantha picks her head up and looks at her.
"No."
"What did he say?" Gabby continues, "Precisely, what were his words when you asked him about wedding planning?"
"'Anything you want, Sweetheart,'" Samantha admits, somewhat begrudgingly. Gabby smiles triumphantly.
"How long have you two been engaged?" she asks, trying to flesh out the picture.
"Two years," Samantha answers. She fiddles with her rings as she says this, no doubt a nervous habit she's picked up in that time. Gabby holds open her palms.
"Give me your hand," she directs. Samantha places her hand in Gabby's open palm as she covers it with her other hand.
"I want you to listen to me very closely," Gabby says, looking Samantha straight in the eye, "Because what I'm about to say is something you are going to need to repeat to yourself every day until you start believing it: This day is about me. Say it."
"This day is about me?" Samantha answers hesitantly. Gabby shakes her head.
"Like you actually believe it, please."
"This day is about me," she repeats, a little more sure.
"Good," Gabby nods, "Now Samantha, you don't seem like a very selfish person to me, but I'm going to let you know right now that it is necessary, no, demanded that you be as selfish as you can on this day." A line of worry creases Samantha's brow.
"I don't want to be a bridezilla," she mumbles. Gabby laughs lightly and shakes her head again.
"It has nothing to do with being a bridezilla," she replies, "Bridezillas occur when there is no room for error or flexibility. Bridezillas have unreasonable demands, and believe me, that is saying a lot in this industry." Gabby lets go of Samantha's hands and leans back in the chair.
"What I'm talking about is…" she hums in thought and stares at the ceiling, "You don't have to make excuses for what you want in your wedding. If you always dreamed of walking down the aisle on horseback, do it! As cliche as it sounds, it's your day… well, you and your fiancé's, technically. Unless they are footing the bill, no one has any right to put their two cents in, and even then there are limits." Gabby takes a breath and rises from her seat. She loves this part, loves empowering brides to really ask for what they want.
"Most people come to weddings for free dinner and an open bar, let's face it. You are providing them a party. Make it the party you want it to be, though. We're going to be putting a lot of work into this in the next few months… Might as well make the final product enjoyable for you."
"But the guest list?" Samantha mumbles. Gabby shakes her head, trying a different tactic.
"Your fiancé? Would you say he's the kind of guy to… pull punches?" Gabby already knows the answer, but a weird sort of satisfaction zings through her as Samantha shakes her head. "OK, so do think if he really wanted something, he'd be passive aggressive about it or would he just say it?"
"He'd tell me." A tiny, affectionate smile crosses her face.
"And he told you to do anything you wanted," Gabby leans against the desk in front of Samantha once more. "I'd say this is a golden opportunity. Now… what was our mantra again?"
"This day is about me," Samantha says decidedly.
"Damn straight," Gabby agrees. She moves behind her desk and grabs a whiteboard off the floor and a marker from her pen cup, uncapping it with her teeth. "Now, first things first, I want you to describe to me how you see your wedding." Samantha smiles and nods.
"I see it at night… Outdoors..."
"You are out of your damn mind!" A rough voice drifts from the waiting area. Gabby and Samantha's attention is drawn away from the assortment of wedding binders at the sound. "There is no way Bradbury was a better sci-fi writer than Vonnegut!"
"Bradbury was much more prolific in his lifetime," Cas' familiar timbre follows.
"Much more prolific? Have you ever heard of 'Quality over Quantity?'" Dean and Cas stumble into the office, hands full of coffee cups and white paper bags. "Hey Sami, how's it going? I picked you up a slice of pie and I don't want to hear any of your dieting bullshit. One slice ain't going to kill you."
"You sister and I were just discussing outdoor venues," Gabby offers, taking her latte and paper sack (Bearclaw! Kickass!) from Cas.
"Outdoors?" Dean raises an eyebrow and gives them a wry look, "What about the 'traditional' church?" Samantha glances at Gabby and then to her brother.
"This day is about me," she says with assurance. A wide smile crosses Dean's face and he looks at Gabby gratefully.
"Glad this one finally made you see the light," he says, throwing a thumb in Gabby's direction, "Now, if she could just do something about that stick up Luke's-"
"Anyway, moving on!" Gabby interrupts, hefting up another book and thrusting it into Dean's arms. "Let's talk about color schemes next."