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all’s well that ends well (to end up with you)

Summary:

She’s trading in her vest for a desk and she couldn’t be happier.

Notes:

Happy Saturday friends! Hope your weekend is off to a good start! This is my third fic for Fictober and it’s my own little alternate reality set in the future after s9….a what could have been for Upstead where s10 doesn’t exist. Hope you enjoy! 💕

Shoutout to shipcago on tumblr and anyone else who recognizes this little plot bunny from a reblog I made ages ago.

Title is taken from lyrics to the song “Lover” by Taylor Swift.

(See the end of the work for more notes.)

Work Text:


"I still can't believe you're really leavin' us."

Hailey looks up from the paperwork in front of her and spins around in her chair to find Kevin staring at her from the other end of the bullpen. There's a softness in his eyes, a reflection of sadness she is sure mirrors her own because she can't quite believe it herself either.

She nods, giving him a sheepish smile as she leans back in her chair, and then she lets out a sigh. "Can't be chasing down the bad guys forever, Kev. Not when I have someone waiting for me to come home to them every night."

He nods back at her, but the melancholy in his eyes remains as he stands from his desk and struts toward her with his arms held open. Her smile widens, a little happier, fuller, and she pulls herself to her feet as he reaches her and wraps her up in a tight embrace.

"Gonna miss you like crazy, girl," Kevin says over her head, and she nods against him, squeezing her arms around his waist as far as they can reach.

"I'm gonna miss you too," she says, forcing back tears she promised wouldn't fall as she squeezes him again. "We'll still see each other though. It's kind of a requirement as godfather, ya know?"

He gives her another squeeze but doesn't let go of her as he pulls his head back just enough to look down and meet her eyes. He shoots her a big toothy grin.

"I love that kid," he says.

"I know you do, and she loves you. Swear some days, she loves you and Vanessa more than she does me and Jay."

"Nah, that kid adores you two. You know she got that man wrapped around her finger too, and she sure as hell knows it."

Hailey laughs, leaning into him again for one more hug. "You're not wrong about that."

"Sorry to interrupt the afterschool special," a voice comes from behind them.

Hailey peeks around Kevin's tall frame to find Trudy Platt standing at the front of the bullpen. Her grey hair is longer now, hanging past her shoulders, and there are a few more crinkles around her eyes beneath her glasses.

"You have some visitors Hailey," Trudy says with a smile, almost proud as she takes a step to the side and heads back downstairs.

"Speak of the devil," Kevin calls out, his mouth curving into a smirk.

Hailey can't help smiling too at the sight of her husband traipsing up the steps, but then her eyes fall to the one-and-a-half-year-old teetering at his side with a little hand tucked into his, and her face nearly splits in half with a dimpled grin.

She pats a hand against Kevin's side as she drops her arms and steps around him to make her way towards her whole world as they come off the top step.

"What are you guys doing here?" Hailey asks, beaming as she closes the distance between them.

"Figured since it's your last day we would surprise you," Jay says, smiling brightly at her.

"You did, huh?"

Hailey squats down and holds out her arms and her daughter tugs her hand free from Jay's and teeters forward, rushing toward her mother with a happy grin and wobbly legs.

"Mama!"

Hailey scoops her up into her arms and holds her to her chest, burying her nose in the little girl's soft blonde curls that are a carbon copy of her own.

"Hi, my girl," she says as she stands to her feet. She settles the little girl against her hip and squeezes her close. "I missed you today. You been good for daddy?"

"Good," the little girl squeals. She turns her head and lifts a hand, pointing a finger to Jay. "Daddy, daddy!"

Hailey tips her head back, laughing as she bounces her daughter against her side. "I'll take that as a yes."

A flash of movement comes from beside them and Hailey glances to her right, breathing out a hearty laugh at Kevin sidling up to them with a dopey grin and open arms.

"Give me the child," Kevin says.

Jay snorts, rolling his eyes. "And a warm hello to you too, Kev."

"Good to see you bro. Miss you," he says, curling his fingers in a wave and nodding toward Hailey. "Now will you please give me my god-baby?"

Hailey shakes her head, but smiles and hands her daughter over nonetheless, and Kevin takes her happily, settling the little girl against his hip.

"Hey Hannah-banana," he says, nearly cooing as he steps away and heads toward his desk.

"Kevy!" The little girl squeals again, squirming in his arms and flopping her head over his shoulder.

Jay blows out a sigh and looks to Hailey as he reaches for her, hooking his thumb through a belt loop of her jeans and throwing his other arm around her waist.

"Now that we have a moment to ourselves," he all but whispers, giving her a grin as he dips his head.

"Nuh uh!" Hailey shakes her head, shooting him a teasing smile and pressing a hand to his chest. "Not here."

Jay breathes out a low laugh, tightening his grip on her and tugging her closer. "We haven't worked together in a while, Hails. I'm pretty sure we're safe. Plus, it's just Kev here."

"Maybe, but you're the one that went all fancy on me. Becoming a sergeant and running the training program at the academy and everything. Gotta keep you on your toes."

"Everyone knows we're married. Hell, we have a kid together. I think we'll be alright. Now come here so I can kiss my wife," he says.

He drops his head and plants a quick kiss to her lips, smiling against her when she loops her arms around him and kisses him back.

"And how 'bout me? You miss me too?" Jay asks, pulling away from her, but just barely.

"You know I do," Hailey mumbles between them. She steals one more kiss from him, then pulls away to meet his eyes again. "Especially around here. Twenty-one hasn't been the same since you left it."

"You told me to go for it," he says with a smug grin that has her wanting to press her lips against his again.

"I know, and I'm glad you did. You're doing great things at the academy…recruiting new blood and showing them the right way. We both know that's not an easy thing to do in this city and I'm so proud of you for it."

His smug face softens into a shy smile as he stares down at her. "Wouldn't have been able to make the jump if it weren't for you."

Hailey gives him a slow nod, her face still beaming for him.

"And in case it wasn't obvious, I missed you too," Jay says, patting a hand against her side.

Hailey gives him another smile and nods because she knows all too well how much he misses her because she has missed him the same every single day since he left the unit. Even years and countless of cases later, and one in particular involving a dead C.I. and a sergeant who had let the grief consume him greatly.

Voight hadn't been the same after Anna died, neither had the team, but things didn't change. He continued running the unit and the city with a heavy hand, policing in the only way he knew how — the wrong way – and Jay couldn't take it. And when the opportunity came to take the sergeant's exam, he grabbed it, aced it, and left the unit he had called home for over a decade.

And now it was Hailey's turn.

She's been on the job just as long as her husband, kicking down doors and running surveillance from one case to the next, and now she's trading in her vest for a desk and she couldn't be happier.

An old friend from Robbery-Homicide had reached out to her a few months ago and tapped her on the shoulder about a new cold case division and she went for it. It meant more paperwork, but it also meant a desk job with somewhat normal business hours that allowed her to be home every night instead of being on-call and forced to leave her daughter and husband behind for days at a time.

She had never been a stranger to stress or chaos with their line of work, but she was ready to slow down and settle and be with her family.

She was so sure it had been stress that made her late while they were cleaning up Voight's mess following Anna's death. He'd fallen off the wagon. Crossing lines, making questionable calls, and Jay had been right there to try and help him through it by lying and making excuses and sneaking around.

But when Hailey realized she was pregnant, she knew a choice would need to be made, one that would either make them better or tear them apart forever.


The jingle of keys from the other side of the apartment door makes Hailey's pulse quicken and she freezes in place on the couch. She sets her hands over her criss-crossed knees and takes a deep breath, braces herself for what is to come once the lock turns and the door opens, but when it does, she doesn't turn around.

Jay's footsteps are heavy as he steps inside and closes the door behind him. He drops his keys down to the entryway table and kicks off his boots, blowing out a breath as he moves further into the room.

"You're home late again," Hailey calls out.

She turns her head slowly, eyeing him over the back of the couch and looking him up and down. Her heart sinks to her gut as she takes him in. He doesn't look like the man she's come to know inside and out for the last six years. Exhaustion and uncertainty take up space in every wrinkle around his eyes. She can't remember the last time she saw him smile.

"You were with Voight."

He knows it's not a question, but the accusation is evident behind her words, and he can't help the tick of his jaw at what she says, and what she doesn't. He figures he has no right to be annoyed though, not when the accusation isn't an accusation at all, but the cold hard truth.

Hailey turns her head, her back to him again as she stares out through the windows and doors of their balcony. She doesn't have it in her to try and hide the heavy sigh she blows out and he can't blame her for the disappointment he hears in it. He's disappointed in himself too.

She leans forward after a quiet moment and pushes herself up off the couch. She grabs her half-eaten take-out and empty glass of water from the coffee table and busies herself with cleaning up from her lone dinner. She grabs a Gatorade out of the refrigerator once she's done and turns to face him, not all that surprised when he doesn't meet her eyes.

He opens his mouth, struggling to find the words to try and fix the damage only to come up short. He shrugs his shoulders and glances to the bedroom door.

"I think I'm gonna take a shower."

Jay has never been a coward, never shown fear, not ever, but now, seeing him like this, it breaks something inside of her. She glances down, holding herself back from setting a hand to her stomach, and then she looks up again and stands a little straighter.

"No," Hailey calls out before he steps away. She rounds the island and sets her drink down on the counter as she stands with one hand on the edge and the other on her hip. Jay turns around, finally looks at her, and she shakes her head at him. "You need to talk to me. I need you to talk to me."

"Hailey – "

"We can't keep doing this, Jay. We can't be a unit dedicated to one neighborhood. We can't look the other way so Voight can play cowboy. No matter how guilty we feel."

"You have nothing to feel guilty about. And Voight – he'll be alright. He's just struggling with Anna's death and...and he's trying to make it right. Make peace with it. I'm trying to help him make peace with it, okay?"

"No, it's not okay! It's not your job to help him through that. You are not responsible for him or his actions or whatever good he thinks he's doing."

"I know," Jay says with a heavy and dejected sigh.

"There's gonna come a point when you can't manage him without changing who you are...any more than you have already."

"I said I know," he bites back with a sharp tongue, but Hailey has never been one to back down from anything and she's sure as hell not gonna start now.

"Do you?"

He takes a step back, as if those two simple words have reached out across distance between them and struck him in the face.

"Excuse me?"

"Do you know?" She asks with unblinking eyes that see right through him. "Because I don't think you do, Jay. We've been here before. Went down this same road a year ago when I went off the deep end. I shut you out and you begged me to talk to you and let you in, and I did. I need you to do the same for me now.

"Whatever this thing is with Voight, whatever you're going through…I need you to talk to me. I need you to let me help you because…because I don't wanna do this on my own."

He looks at her then, really looks at her, and it feels like the first time in a long time.

"What is that supposed to mean? Do what?"

"It means I'm pregnant," Hailey says with a casual shrug as if they're just talking about the weather. "I'm pregnant and I've been trying to figure out how to tell you these last few weeks, but you just haven't been here. You haven't been around."

He barely even reacts, and it only further confirms for her what she knows she needs to do, so she takes one more deep breath and then lays it all out.

"I can do it by myself if I have to Jay, but I don't want to. And throwing an ultimatum at you is the last thing I wanna be doing right now, but I don't know what else to do, so it's me and this baby, or it's Voight. It's your choice. I just don't wanna do this anymore," Hailey says, waving a hand between them. "I don't wanna fight with you and I don't wanna walk on eggshells around you. I can't do it."

Her gaze lingers on him, but still he says nothing, just stands there like a deer frozen in headlights. She nods slowly, blows out a breath, and then grabs her Gatorade and steps away from the counter.

"Your dinner is in the fridge," she mutters as she passes him.

Her mundane tone could make him cry right then; she's just reamed him out, and yet she's still looking out for him, and he doesn't deserve it, doesn't deserve her.

And as she walks away from him and disappears behind the half-open door of their bedroom, her words ring in his ears, the weight of them hitting him in the chest. His wife just told him she's pregnant, and he didn't even bat an eye, didn't say a word.

He stumbles forward and falls onto a stool at the island and lifts a trembling hand to his chest. He breathes through the panic and the realization of the very real possibility that he's about to lose the most important thing in his life.

It's as if he needs to remind himself to breathe, so he sucks in deeply and blows it out, over and over for what feels like hours when it's barely been a minute, and then he pulls himself to his feet. He rushes to the bedroom and pushes open the door to find the bed empty and moves across the room just as the bathroom door opens.

Hailey stands there in her sleep shorts and a tank top, but it's the sight of her red, tear-filled eyes that hits him square in the chest again. He takes one large stride before he's standing in front of her, and then he throws his hands out to hold the sides of her face and takes her by surprise when he crushes his lips against hers.

She barely has time to register that he's even kissing her with eyes still open until they flutter closed as he kisses her in a way that makes her bones ache. In a way that reminds her of who her husband used to be.

She lifts her arms and curls her hands around his biceps, and he wonders for a moment if she's gonna push him away, but she pulls him closer instead, and kisses him back. She gasps when they separate, only enough space between them to find their breath, and then she sees the tears in his eyes and the guilt across his face.

"I'm sorry," Jay chokes out with a tremble in his voice. He holds the side of her face still, not ready to let her go in more ways than one.

"I'm sorry…s-so sorry," he says again. He doesn't give her a chance to say anything and leans down again, peppering her with kisses to her lips and cheeks, chin, and forehead. He drops his hands from her face to loop his arms around her waist and pull her against him, and then presses his nose to her neck and kisses her there too. "I want you, and I want this baby. Choosing between you or Voight...there's no question. It's no contest. It'll always be you, Hailey."


Things changed after that night, and no one seemed all that surprised when Jay announced he was leaving Intelligence a few months later. And when he did, it was as if a switch had been flipped and he found his old self again, his true self. The good and bad, right and wrong that he craved; everything was black and white again and allowed him to see clearly for the first time in months. He'd been at the academy for almost two years now, plucking those he thought had potential and molding them into officers that the city they called home deserved to have.

It didn't take long for them to tell everyone they were expecting. The job is hard and dangerous, and neither were willing to risk it, not for anything or anyone.

Pulling back was one of the easiest decisions Hailey had ever made, and she was more than happy to ride a desk for most of her pregnancy. And when her daughter arrived it was a different kind of rush that would never come close to chasing down the bad guys. She was a mother, and she couldn't lose that, wouldn't ever take it for granted.

And as she thinks back on that time of her life, and the last decade and then some of her career and how today is the last day she'll be in the bullpen where everything changed for her and for Jay, she can't help thinking back to his last day too. Another day when everything changed even though it was for the better.


It wasn't goodbye, she knew that, and she knew she'd see him at home and fall asleep beside him in their bed, but it cast a bittersweet taste in her mouth all the same.

"Doesn't seem real that this is happening…you leaving Intelligence," Hailey says as they step outside from the roll-up.

Jay follows behind her with a box of his belongings from years at twenty-one and they make their way across the parking lot. He puts the box in the backseat of the truck and meets her at the hood, reaching for her hand immediately.

"It's gonna be weird not seeing you all day, every day," she says with a sad smile.

"You'll still see me every day," he reminds her, squeezing her fingers between his.

Hailey nods and squeezes back, taking a step closer towards him and reaching for him with her other hand. She fingers the zipper of his jacket, and nods again.

"You know I trust the team with my life, and even though I'm riding a desk, I'll never trust anyone to have my six the way I trust you."

"I'll always have your six," Jay assures her, but it's an assurance she hardly needs. She knows he'll have her back always, just as she'll have his, but as much as change is inevitable, that doesn't make it any less hard to bear either.

"We're gonna be okay, Hailey. This is the right move. For me and for us," he says, lifting his other hand between them and placing it over the barely noticeable bump beneath her sweater. "For our future. I'm sure of it."

"I know," Hailey says, sniffing back the tears that threaten to spill from her eyes. "And I know I'm gonna see you at home and we'll still be us, but…but I still feel like I'm saying goodbye. You're the best partner I've ever had on the job. And you're a good man…the best man."

He pulls his hand from her stomach and tugs on her fingers, pulling her closer and lifting an arm around her shoulders.

"I love you. I love you both…so damn much, Hailey," he says, hugging her and squeezing her against him.

She loops her arms around his waist to hug him back, and then pulls her head away to look him in the eyes. "We love you too."

He smiles at her with a sweet grin that is only for her and their unborn child and dips his chin to press a kiss to her forehead.


A small smile creeps out across Hailey's face and Jay squeezes her side.

"What are you thinking about?"

"Your last day in Intelligence," Hailey murmurs.

He nods slowly, his hand sliding around her waist to her lower back. "That was a hard one."

"It was," she says, nodding too and casting a glance to the little girl sat in Kevin's lap across the room. "But as hard as it was to not have you here with me, it was worth it. We might not have this otherwise…us, our family. I love where we are now, our life together. And I love you…even more now than back then. More than I ever thought possible."

"I love you too, and I love our family. It's bigger than any job, Hailey."

She nods, lifting her hands to the sides of his neck, fingertips grazing over his skin. "It is. It's everything."

"You ready to get outta here then? Need help with anything?"

"Nope. I loaded all my stuff into the Jeep already, and I said goodbye to the rest of the team before they headed out on a case earlier. Kev and I were finishing up some last-minute paperwork when you got here," she says, giving him another soft smile and a brush of her thumb across his cheek. "Let's go home."

He nods back at her with another smile, and they pull away from one another.

They manage to pull their girl from her favorite uncle's arms, and after a few more teary goodbyes with Kevin and Trudy that aren't really a goodbye, but a see you later, Hailey and Jay walk down the steps of twenty-one for the last time with their daughter between them.

Hailey heads for her Jeep, and Jay heads for the Ram. He gets their girl in her car seat, closes the door, and then turns to the parking spot beside his.

"See you at home, partner," Jay calls out before Hailey closes her door.

She quirks an eyebrow at him, and he raises one back at her.

"What?"

"We haven't been partners for a while, but I still love it when you call me that. Even after all this time," Hailey says, smiling softly at him.

He takes the few steps toward her and leans into the Jeep, smiling that sweet grin at her again as he slants his mouth over hers. He kisses her deeply, grinning wider when she moans into him and kisses him back.

"You'll always be my partner," Jay whispers between them, pecking her lips once more before he pulls away.

They may not be partners on the job anymore, but they are as husband and wife and at home with their daughter, and it's in those ways that mean the most. It means everything.

Notes:

Thank you for reading! Kudos and comments are always loved and appreciated.

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