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“You wanna go to Kelly and Stella’s wedding with me?” Jay innocently asks Hailey one morning, while they’re having breakfast around her kitchen island.
Hailey nearly spits out the coffee she’d been sipping, but quickly recovers. “Well, I kind of assumed we would be going together? We went to Cruz's wedding together.” The blonde reminds him.
“Yeah, but what if this time was a little different?” He suggests. “What if now you go as my date?”
“So you want to tell people we’re dating then?” She inquires, slightly taken aback. They have been together long enough to have moved past the ‘wanting to keep things quiet to prove they could be the same work partners while also being in a romantic relationship’ stage, yet somehow they’re still stuck there. To be honest, Hailey isn’t quite sure of the real reason why they hadn’t told people about their relationship eight months in now; it just never felt like the right time to be their moment, with Kim getting abducted and shot, then the whole fallout with Voight, Squad 3 being hospitalized for weeks after they nearly drowned in that boating accident rescue, and Will’s disciplinary hearings about the meds that Natalie had stolen from his trial.
Needless to say, a lot had been going on in their sphere since they finally took that step together, and it often slips her mind that their friends are still unaware of the best thing going on in her life right now.
Jay must have taken her silence as a rejection, because before she has time to snap herself out of her winding thoughts and formulate a proper response, her boyfriend starts rambling: “I mean, if you’re not ready, that’s okay. We can wait then… You know I’d wait for you, right? We’ve been through so much these past several months, and the last thing I want to do is pressure you into something you’re not ready for yet… But Hailey, I just want you to know that I really wanna slow dance with you in front of all our friends, to be able to kiss your cheek at Molly’s after a long day at work, and to tell the people who matter most to us how much you mean to me.”
“Yeah?” She answers, her bright blue eyes wide, hardly believing what she is hearing.
“Yeah.” He affirms with a twinkle in his eyes now, having never uttered words he believed in more.
“Okay, let’s do it then.”
“You serious?” Jay sounds so hopeful. And it makes Hailey once again wonder why they’ve waited this long.
“I’d love nothing more than to slow dance with you in front of all our friends.”
“Really? But you hate dancing.”
“Yeah, but I love you. And I can tell that this is clearly important to you. So, let’s do it.” Hailey confirms with a simple nod of her head. “We’re telling them tonight at Molly’s though. There’s no way I am ruining Stella and Severide’s day by making it about us. That’s their day and theirs alone. We are not stealing any of their thunder. All attention should be on them.”
Jay jumps up from his stool and places a delicate kiss on his girlfriend’s supple lips. “I love you so much, Hailey Anne.”
“I love you too.” The blonde whispers before immediately recapturing his radiant smile.
Telling their friends after all this time has Hailey’s stomach in knots. How would they react? Would they be happy for them (she really hopes they will be) or would they be mad that they kept it hidden for so long?
“Hey,” Jay gently brings Hailey’s attention back to the moment with a slight squeeze of their dominant hands. “You sure you still want to do this? It’s not too late to back out.”
Hailey looks up into her boyfriend’s green eyes, seeing nothing but love reflect back in them.
“I’m sure.” The blonde reaffirms. Her free hand finds its way to the door handle of the bar they all love and frequent. But before she can push the door open, Jay speaks up again.
“Remember, I love you.”
“I love you too, Jay. So much.”
Jay softly plants a quick kiss on Hailey’s cheek and gives her hand another reassuring squeeze before she pushes the door open and the couple crosses the threshold.
The Friday night buzz means the place is quite crowded, but Jay and Hailey easily spot their friends and co-workers gathered around the bar.
“NO WAY!” A voice suddenly breaks through the overlapping conversations and music, causing the whole bar to fall silent.
“No freaking way!” Kim screams again. “Everyone stay calm, it is finally happening.” She announces to the entire bar, motioning to Jay and Hailey’s intertwined hands.
Their friends break out in cheers and various forms of ‘finally’ and ‘took you two long enough’, with even some wolf whistles from Kelly, Adam, and Kevin thrown into the mix.
Hailey’s cheeks flush tomato red when she realizes all eyes are on them, and Jay visibly swallows. The couple give each other one more encouraging squeeze to also ground themselves.
As calm as the bar had been when the couple walked in a few seconds ago, pure chaos lay before them with their friends firing off countless questions in their direction at once.
“Hey, we got this. And I got you. No matter what.” Jay whispers before letting Hailey get ushered away by Stella and Kim, who seem like they might jump out of their own skin if they don’t hear all the juicy details from Hailey as soon as possible.
“Oh my God, girl! Tell us everything!” Stella starts.
“Yes, starting with how long. We must settle who has won ‘the Upstead bet’.” Burgess states.
“The what now?” Hailey presses, not sure she’s following along.
“‘The Upstead bet’. You know: Upton and Halstead, Upstead.” Kim clarifies.
Hailey lets out a chuckle. “You do realize how ridiculous that sounds, right?”
“Oh, and what would you prefer, Mrs. Halstead?” Kidd teases.
“I believe you’re the one getting married next week, Mrs. Severide.” Hailey bites back.
“Actually, I’m keeping my own name, but that’s besides the point here. You and Halstead, how long has that been going on?” Stella redirects.
“Sorry, but what is this you were all saying about a bet? You guys have been betting on us getting together?” The detective can’t believe this revelation.
“Technically, this is the third go-around.” Kim proudly explains. “The predictions of the first and second rounds came and went without any confirmation from you lovebirds, so we’re actually on poll number three now. It started within just intelligence 3 years ago, but then it grew to include Trudy, Stella, Severide, and Will. Now I think half of the crew from 51 and Med are in on it too?”
“3 years ago?!” Upton’s mouth falls open.
“Yeah girlfriend, you two weren’t exactly secretive about your feelings. Maybe to each other, but we could all read it on your faces from miles away. Quite surprised it took you two this long to figure it out and take the plunge.” Stella adds.
“I can’t believe this!” Hailey runs a hand over her face and through her hair.
“Stop deflecting, and tell me when your man Halstead finally grew a pair.” Kidd implores.
“What makes you so sure he made the first move?” Hailey asks with a wicked grin. That playful implication catches her friends off guard as they both peak up at that.
“No way. Hailey Upton, I am impressed.” The firefighter answers.
“I’d like to butt in and declare that I did kiss her first.” Jay interrupts as he hands Hailey a drink. “Here.”
“Thanks.” Hailey accepts the drink from her boyfriend before continuing the conversation with her friends. “Only after I basically told you I turned down that FBI offer for you and had to spell it out that I had feelings for you.”
“Details, Upton. Details.” Jay retorts, winking at his girlfriend then heading back over to Adam, Kevin, Will, Severide, and some other guys from Firehouse 51.
“The FBI offer? Hailey, that was months ago. MONTHS!” Kim recalls.
“Yeah, a little over eight months.” Hailey confirms.
“I need to sit down.” Burgess emphatically (and quite dramatically) collapses onto a nearby bar stool.
“Did Upton just say eight months? Ha, that means I win!” Herrmann butts into the conversation.
Hailey sends him a puzzled look.
“A bartender notices more than just people’s drinking habits, Detective.” The firefighter explains. “Plus, the heart eyes you two have been throwing at each other for so long now were pretty hard to miss. Along with those hickeys you tried to hide after your little trip to the bathroom a few months back.”
Hailey feels the blood rush to her cheeks in embarrassment, while her hand shoots up to her neck to cover the since-faded marks Jay had left two months into their relationship in the back of Molly’s because he just couldn't seem to control himself that night.
“I can’t believe I actually lived to see this day. Was worried one of you had to get shot again for you to finally confess your feelings for each other.” Stella proclaims.
“Please, don’t even go there. I swear that guy is a bullet magnet. I did not sign up for this.” Upton quips.
“Except now you did.” Kim reminds her.
Hailey’s eyes find Jay, who seems to be roped into a similar conversation with the guys near the bar, and she cannot help the smile that overtakes her face. “Yeah, I guess I did.”
“Oh, shut up! Could you look any more in love? You make me look bad, and I’m the one getting married next week.” Kidd calls out the blonde.
“I’ve gotta text Trudy. She’s gonna be so mad she missed this moment.” Burgess declares before typing away to their desk sergeant.
“Trudy knows.” Hailey admits.
“Excuse me, WHAT?!” Kim cannot believe her ears.
“You told Platt, but not us? I’m hurt, Upton.” Stella adds.
“She kinda just figured it out herself, to be honest. Her, Will, and Voight were the only ones that knew before tonight.”
“WILL HALSTEAD, YOU KNEW AND DIDN’T TELL US?!” Kim yells dramatically at the redhead, who looks panicked as the fierce brunette heads toward him.
The entire bar breaks out in laughter as they watch Burgess chase Will through the Molly’s crowd.
Jay reconnects with Hailey, now sporting an amused grin. “You glad we told them?”
Hailey nods eagerly as she observes their gregarious friends continue on with their various conversations around them. “Yeah, I am. Because now I get to do this.” The blonde perches on her tiptoes and presses a soft and tender kiss to Jay’s lips, which proudly match her daring move.
They keep the wild night of celebration going later that night in the privacy of Hailey’s apartment with soft kisses, light touches, and dirty whispers in between the sheets.
It’s simply refreshing to now be able to publicly display their affection for one another and not have to hide their relationship anymore. They could finally touch, kiss, and look at each other with their trademark heart eyes without worrying about onlookers.
After a week filled with tons of teasing from their friends, Hailey and Jay find themselves at their friends’ wedding. Stella looks absolutely gorgeous in her wedding dress. And when the vows are exchanged, there’s barely a dry eye in the room.
It’s a beautiful ceremony, and as the couple at the altar say ‘I do’, Jay softly squeezes Hailey’s hand: a promise that the two of them would be up there someday. The thought alone makes butterflies erupt in Hailey’s stomach when she lets her mind wonder what her future wedding day could look like.
After all the traditional wedding festivities, including dinner with a toast, speeches from Stella and Severide’s closest friends, cutting the cake, and the newlyweds’ first dance, the party had naturally broken into smaller groups.
“Bro, we thought the heart eyes were unbearable before you guys were dating. But damn are you whipped for Upton.” Kevin jokes.
But his humor falls on deaf ears as Jay’s fixated on his girlfriend talking to Herrmann at the bar.
“Earth to Halstead...” Atwater continues.
“Jay, bro! Come back to us!” Adam interjects while waving a hand in front of the detective’s face.
Jay finally whips his head back to his friends. “Huh?”
“Yeah, our point exactly.” Ruzek chuckles.
But Jay’s attention is once again focused on the beautiful blonde making her way back over to the trio with a champagne flute in each hand.
“Later, dude.” Kevin bids farewell as he and Adam head toward the open bar for their own refreshments.
“Here.” Hailey hands Jay one of the champagne flutes.
He flashes her a grateful smile before gently clinking their glasses together. “Cheers.”
“Cheers.”
“What was that about?” she questions, referring to his previous interaction with their colleagues.
“Who knows.”
“Clearly not you.” Hailey teases. “What’s got you so distracted, Halstead?”
“Oh, come on, you know exactly what.” Jay states, checking out his date in the ravishing navy blue dress she wore for the special occasion. “Or should I say who?”
“Hmm, maybe.” Hailey acknowledges.
“Do you wanna dance?”
“I’m usually not too keen on dancing, but if my memory serves me correctly, I did promise you a slow dance or two.”
“Can’t go breaking that promise now, can you? Come on.” Jay grabs Hailey’s champagne glass from her grasp and sets it down with his own before taking her hand and eagerly pulling her toward where the newlywed couple amongst their other friends have been dancing.
“You’re something else, Halstead. You know that, right?” Hailey admits, her voice laced with laughter and happiness as she follows her boyfriend to the dance floor.
“Look, I’m glad Jay and Hailey finally got their heads out of their asses and realized they love each other, but do they have to be so goddamn loud about it?” Ruzek can’t contain his fly-on-the-wall observations any longer.
“Wanna bet the next wedding we’ll be at will be theirs?” Atwater says half-jokingly.
“Oh 100%, dude.” Adam confirms.
“Bet you he’ll ask her before Christmas.” Kevin suggests.
“Please, there is no way he can wait that much longer. My brother is ready to drop down on one knee right here and now.” Will jumps in as he approaches the pair of officers, gesturing towards Hailey and Jay on the dance floor with beaming smiles on their faces.
“I’m not sure I’ve ever seen two people this lost in shared happiness before.” Kevin acknowledges following the doctor’s gaze.
“I think I’ve seen Jay smile as much in the past week as I had in the eight years I’ve known him.” Adam adds.
“I hope they’ll always make each other this happy.” Will states, feeling over the moon to see his younger brother this carefree and in love as he deserves.
“Of course, they will. They’re Jay and Hailey after all.” Adam simply concludes.
“Yeah, you’re right. Those two are basically the textbook definition of soulmates. I can’t believe how soft Upton gets around him.” Kevin agrees.
“Don’t let her hear you, bro. She’ll have your balls on a stick.” Adam jokes.
The three friends break out laughing because the petite blonde really could kick all of their asses if she wanted or needed to. Hailey may be soft around Jay Halstead, but she’s undoubtedly a badass and not afraid to show it.
Over on the dance floor, Jay and Hailey are completely wrapped up in each other, drowning out their loud and drunk co-workers and friends enjoying the open bar and creating that wedding buzz around them. To the couple though, it’s as if they don’t even exist in their little world. They’re so engaged in the way their bodies move so comfortably together along to the music.
Moments later, Hailey shifts her head from resting on her boyfriend’s chest to look him in the eyes. “Jay, everyone is staring.”
“So let them? I can’t blame them for looking at the prettiest girl in this room.” His eyes locked on hers.
“Jay, you’re not supposed to say that when the bride is quite literally in the same room.” She tries to stop the smile breaking out on her face.
“Hails, don’t get me wrong, Stella looks beautiful in that dress. Stunning even, but she’s got nothing on you. You’re easily the most beautiful person in this room. Hell, in this city probably.”
“You didn’t--” Hailey can no longer contain the grin from overtaking her face. “Oh, man. What am I gonna do with you?”
“Hmm, I don’t know… but I think you should marry me one day, Hailey Anne.”
The words slip so easily from his mouth. It’s not a proposal, Hailey knows. It’s way too soon. But it’s a promise. A promise that one day, she will be in a place like this again surrounded by their beloved friends and fellow first responders, dancing in the arms of the love of her life as they get totally consumed by the rare occasion. Only then, she’ll be the one in the white dress.
And honestly, when she lets herself really think about it, she realizes that that day cannot come soon enough for either of them now.
“Yeah, I think I will.”