what, like it's hard?
Warnings: Brief mentions of crimes, court/legal system, intelligence-typical things, canon-typical injuries
Summary: 5 times intelligence noticed yours and Jay's 'friendship' and 1 time they figured it all out.
A/N: Final assignment submitted and I just realised I haven't written in a little bit so here you guys go! This thought came to me so suddenly and randomly, please don't question it. I have no idea about anything surrounding law so please don't mind any mistakes. I haven't written for Jay in a while and I wrote 4k words soooooo I hope you all enjoy!!
1.
Kim hadn't been working in Intelligence long till she met you.
She had known most of the guys up in Intelligence, but she never stuck around long enough to bump into you. It wasn't until Intelligence was being summoned to be witnesses in a court trial that she even heard of your name.
It was as if you sensed the peaceful lull they luckily found themselves in after suffering the past almost month with back-to-back cases. Without any escorting, you ever so casually strolled into the bullpen, heels sharp as ever as the sound reverberated through the previously silent upstairs.
The reaction was decently mixed. The general consensus seemed to be that they were happy to see you with one sigh and someone mumbling incoherently under their breath.
Face brightening, Erin got up from her seat and offered you a one-armed hug.
"Y/N! It's been so long, you here for the Whiteman case?"
"Hey guys, yeah unfortunately. My boss has got us working overtime trying to nail this guy." Your voice was soft and soothing, firm with enough authority that Kim could already tell you easily commandeered every room you walked into. "I'm here to go over your guys' statements and any questions you might be asked on the stand, just the usual stuff."
As you spoke, your eyes trailed over everyone, all their focuses homed in on you, but your journey seemingly stopped on a very specific green-eyed man who was trying his best to not flush under your eyes that all of a sudden felt all too leering.
Smirking, your lipstick covered lips perking ever so perfectly, you looked away first and addressed Erin. "Why don't we start with you since from what I've read, you were the most personally involved."
Humming in assent, Antonio moved to let you station yourself at his desk, stopping to lean against Jay's desk, the latter's eyes still firmly glued to you, or more specifically, your figure that was donning a fitted blazer and pencil skirt.
"Why don't you do anything about it?" Antonio murmured, amusement clear in his tone as he watched the younger man flush and force his eyes up towards your face, but his pale skin wasn't helping him a single bit.
Antonio was one of the few who witnessed the first time Jay had met you and now, several years later, he was pleasantly surprised to see both of you remained blissfully single.
He was slowly starting to get sick of Halstead's pining and he was worried he'd lose out on the money he put in years ago. It was high enough now that he could pay off a decent chunk of Eva's eventual college tuition.
Clearing his throat, Jay dragged a hand down his face, physically having to turn his chair around to face his computer in the opposite direction to his biggest distraction.
"Stop talking Antonio and quit slacking, you're up next."
If Kim wasn't so focused on the questions you were asking, she would've noticed the familiar and longing look you and Jay exchanged from across the room.
2.
Following your first meeting, Kim had the pleasure of not only seeing you several more times but also getting to know you on a more personal level.
Outside of the job, you were so sweet and lovely that it was almost cavity inducing. A few drinks at Molly's and they uncovered a giggly and surprisingly cuddly you who, unfortunately for them, kept secrets sealed as tight as fort knox.
You were a decent cook but an excellent baker when time permitted it and to say you weren't struggling with money would be an understatement.
Several times she had seen you in court with immaculate pant suits and stupidly expensive heels which followed you outside in your day-to-day life. It was safe to say that she didn't blink an eye when you casually strolled into work one day with a Birkin like it wasn't the most expensive thing to ever be in any of their proximities.
The familiar rhythm of your heels click-clacking brought her out of her stupor. She turned and found herself rolling her eyes at how the other lawyersâ eyes were drawn to the hypnotic swaying of your hips as you strode down the hallway.
"Mr Sinclair, I see you're still representing all the scum of the earth."
Damn, not even a hello.
Said man stammered, straightening up his tie as he tried getting himself together but failed to do so in time.
"Why don't we talk in private, just you and me, I'm sure we can come to some sort of agreement."
Without waiting for a reply from him, you smiled, lips painted so perfectly Kim was able to admit she was jealous and wanted to know your ways, you side-stepped the man but before you could leave, you shoved your Birkin into Jay's chest, his hands frantically trying to keep hold of it.
Acting like that hadn't just happened, you confidently walked away, not batting a single perfectly curled eyelash to see if the other lawyer was following or if Jay had caught one of the pride and joys of your life.
Pretending like Kim hadn't just watched him be a small disaster that he usually never was unless it involved you and you only, Jay exhaled loudly, his face reading that he was disturbed and wanted to be doing literally anything else, but his actions spoke for themselves.
He kept a firm hold of your bag, his arms keeping such a secure hold that one would think the bag contained the world's most precious jewels.
Kim was now more than well-versed in the flirty relationship between you and Jay that you both vaguely swore, separately, that you weren't going to ask the other out.
During the few times she saw you and Jay in the same room together, she was forced to witness the blushing disaster that the detective would become every single time he lay eyes on you, but he was still as sharp-tongued as usual, but his words were laced with a softness only a select few were graced with.
She was forced to suffer your casual banter and flirty quips, both of your shared physical attraction for the other and how easily Jay folded the second you opened your mouth.
Kim had never put money into a betting pool quicker than she did after watching you and Jay interact on three separate occasions.
Wiggling her brows at him, a suggestive smirk making the man swallow a scoff, he rolled his eyes and walked into the bullpen, your Birkin still held preciously in his arms, only letting go once he got to his desk, gently setting it down beside a stack of files as if he knew exactly how much care to handle it with.
Kim tried not to think too much into how practised his moves were, handling a ridiculously expensive bag as if this were just another day when his wages were very indicative of the life he was living and considering of what she knew of his childhood living circumstances, he never would've even thought of such expensive notions even existing.
Much food for thought but before Kim could make a sly comment, Mr Sinclair came storming back, face red and smoke billowing out his ears as he went towards were his client was detained.
Your relaxed demeanour and satisfied smile told them everything they needed to know.
3.
The next time Kim saw you, it was under circumstances she wished they could have avoided.
The call came to Jay on his personal phone, apparently Will called him saying he needed to come to Med with very few words and Jay was already out the bullpen before he hung up the phone.
Following after him upon Voight's command, Kim barely kept up and felt a sense of dread and anxiety when he gave her the rundown.
It seemed that they got to Med in record time and Kim found herself trying to keep up with Jay who was speed walking faster than she'd ever seen him.
Following Will's directions to the correct treatment room, Kim felt her shoulders lose some of its built-up tension at the lack of a horrible disaster.
You definitely looked worse for wear. Your hair mused and lacking its usual sleekness, blood already coagulating at your temples and the dirt was made more apparent due to the red dress you were wearing.
Despite the circumstances, you still looked smoking hot and Kim found herself internally cursing you out for being effortlessly gorgeous, she was slightly jealous that you still pulled off being a mess.
"What happened?"
Jay had also become less tense, but his concern was still strong, eyes roaming over your body and zeroing in on the gauze you were holding at your bicep.
"Drunk guy was trying to get handsy with Emily." Kim recognised the name to be one of your college friends. "She pushed him away and when his friends tried getting involved, obviously we had to get involved."
Definitely not a nightmare but not an ideal situation either.
Continuing to look you over, keeping an ear out as you resumed your story, Kim quickly backed up and looked back up to your hand.
Looking at the other woman whose mouth was agape, you followed her line of sight and couldn't help yourself when you giggled.
Wiggling your fingers, you softly smiled down and let Kim look closer.
"When did you get engaged!?"
Unable to keep down your biggest smile, you found yourself feeling giddy, the same warm butterflies every time you told someone about your engagement.
"Last week, that's why me and my friends were out today, we were celebrating my engagement and my promotion."
Kim nodded, a soft ooh before whistling at the rock casually adorning your finger.
"Oh yeah, Jay told us a few weeks ago about the promotion, deputy district attorney is amazing! Congratulations, on both things."
Giggling again, you breathlessly thanked the brunette woman, your eyes slyly looking at the only man in the room with you.
Only when they finished tying up any and all loose ties with you did they leave and only once they got back in Jay's truck did Kim say anything.
"You didn't look that surprised when she said she's engaged."
Jay remained quiet, eyes forward on the road and both hands on the wheel.
He hummed, "I already knew."
Kim tried not to feel too bad, stuck between her elation for her friendâs engagement and her sympathy for her other friend who she knew had feelings for you.
"You know her fiancĂŠ then?"
Jay just hummed again, a slight twitch in his eyebrows but he didn't look as bothered or as disappointed as she would've thought.
The truck remained silent, both Jay and Kim ruminating in their thoughts.
Just as the light turned green, it suddenly hit her.
No one won the bet, none of them even thought of this turning out to be a possibility.
Damn, what were the going to do with all that money now?
4.
When Jay got shot, no one even pretended to act too surprised.
Obviously, they were shocked for all of two minutes before the man himself insisted one of them drove him to Med and he'd convince Will to check him out and he'd be back to work in no time.
Kim just so happened to draw the short straw, being the last one to say, 'not it' and touch her nose. She claims to have been distracted by her phone which everyone knew was safely tucked into her pocket.
Unsurprisingly, Will made a big fuss. Concerned alongside his brotherly annoyance, at times being purposely harsh just to get back at Jay for getting hurt excessively.
Wrapping up his wounds, Will roughly summarised what he should be doing going forward and how long he should be off work before he looked at his injured brother pointedly.
"And make sure you tell her otherwise I will, and trust me, it won't be pretty."
If they weren't brothers and Kim wasn't used to their banter, she would've thought he was threatening him, but when she turned to look at Jay, his split-second reaction made it seem that it was not just a joke but a genuine threat.
Seeing that Jay needed a moment alone to make a phone call, she excused herself to call Voight and update him on Jay's wellbeing.
She tried to waste some time after hanging up by catching up with Maggie and getting a drink from the vending machine but quickly found herself bored and walking back to Jay's treatment room to see if he was ready to leave.
"I promise you don't have to fly back. I can wait but your work in New York can't."
Jay's tone was placating and a lot softer than she was used to hearing from him.
"Yes, I promise it isn't too bad, you can even call Will and ask... Yes, I even promise to take it easy this time."
Woah, Kim wasn't even sure if 'taking it easy' were words in Jay's vocabulary.
If not for the sudden screeching of an ambulance and the rush of noise from paramedics loudly announcing vitals and medical staff zooming past her, she would've heard Jay exchange i love yous with the mysterious woman over the phone.
Once the group moved away and she heard Jay's conversation finish, she stood in the doorway of his treatment room, knocking on the glass to get his attention.
"Ready to go?"
Wordlessly nodding, Jay rose with ease and followed her, waving to Will and walking out the ED without any effort that it seemed like he wasn't shot thirty minutes ago.
"Who was that on the phone?" Kim couldn't help herself, curiosity getting the best of her.
"Y/N" Jay replied, looking nonplussed by her question.
Oh, Kim was so sure he had been talking to a potential girlfriend when he was really just talking to you.
If Kim wasn't then swept up away in Adam calling her, saying they were needed back, resulting in her rushing to drive Jay home and then speed back to work, she would've connected the dots that you also were in New York for a high-profile lawsuit.
5.
When Jay randomly announced he booked off work, time stood still. Everyone thought they were hearing things, experiencing a group hallucination in real time or they were all going crazy at the end of their shift, but Jay clarified that they had indeed, heard correctly.
Not only was he taking time off work for the first time since they all knew him that wasn't just to recover from on-the-job injuries, but he was taking two weeks off and he wasn't elaborating any further.
When Kim asked if you knew considering how close you were, he simply said 'yeah, she knows.'
You also were out of state, having flown back home to get married because you and your soon-to-be husband in two days wanted to get married with all your family present since he, apparently, had a very, very small family.
When they all couldn't get off work to attend, Kim was so assured Jay would be attending your wedding but with this new announcement, she wasn't sure what to think.
Obviously, he got an invitation, all of Intelligence did, but why did it now seem like he was purposefully going out of town to not go?
Maybe Kim was just thinking too much into it.
Finishing their shift together, everyone sent Jay their well wishes and hoped for a good flight before he drove off.
For the next two weeks, no one heard from him and none of them really tried to check in much. The man deserved some time to de-stress and relax without any reminders of Chicago or work.
When he Jay came back, Kim wasn't even trying to be dramatic, but he was glowing.
There was a tan that indicated he went somewhere warm, his body loose and relaxed in a way that showed he truly let go during his holiday and it was comforting to know he had been able to enjoy himself and his smile was warm and full of life that was usually drained out of all of them, their work draining them all of said life.
He looked rejuvenated in a way that made Kim strongly consider taking time off herself and get out of Chicago.
Jay remained secretive of where he went and what he got up to, but his smile was very telling. They could all tell he thoroughly enjoyed himself. If not for that, they all would've poked him harder.
Over the next week, they all got lost in the cycle that was their lives, constant home then work, work then home and it was somewhere in-between that Kim got some intel on your wedding.
Mikayla was sleeping and all the chores had been done, giving Kim a rare moment of pure relaxation. So she had a show running, a mask on her face while she indulged in at least thirty minutes of scrolling on her phone.
When she found herself getting bored of instagram, she quickly refreshed it but before she could exit the app, she was met with a few new posts from you.
Pleasantly surprised, Kim looked at the first picture and your caption and smiled instantly.
Swiping through the pictures, she saw behind the scenes of you and people she could tell were family just from how similar you all looked, and multiple moments from the wedding and the reception.
You looked stunning in your dress and the picture of yours and your husbands ring clad hands made her jaw drop because with the professional camera, your ring looked even more expensive than usual.
Hearting both your posts of your wedding, she scrolled to the final post and her jaw immediately dropped.
You had posted a dump of your weeklong honeymoon, and the first picture was you posing on the beach. You looked so sexy in your beachwear Kim was more jealous than usual, her envy directed mostly at your new husband.
Swiping through, her smile remained as she looked through each picture of the scenery, the food and yourself. It was clear that most the images of you were taken by your husband but there weren't many of him.
There was the occasional show of his hand and the lower half of his body and Kim quickly swiped to the next picture when she got to the one of his glistening half-naked torso.
Hearting your final post, she went to leave comments on all of your posts, her comment filled with congratulations and love and compliments joined the ranks of all your friends and families.
If not for the see of comments she didn't even bother navigating, she would have noticed the comments Jay left behind, his words not one from a friend and the hearts definitely not platonic.
+1
The only reason Kim liked coming to court was because it meant that she wasn't really working. It was always during work hours, but they barely did any actual work, it was so minimal it was sort of like a day off.
The case that Intelligence was part of was happening in over an hour and you had asked them all to come into your office beforehand.
Since you got promoted, you didn't do as much work with them as you used to but because of the severity of their case, you gladly took it on.
It had been two years since you got married and due to how busy their lives were, both in and outside of work, they never got around to meeting your husband.
In the few times they did see you at work, you always laughed it off when any of them complained and it seemed that despite being married and the possible girlfriend Jay had, your relationship dynamic hadn't changed.
Kim didn't want to think about it too much otherwise she'd feel some unsavoury emotions that she really didn't want to face, neither did she want to confront either of her friends.
Entering your office, the room the exact same to how it was the last time Kim was here, she realised you were nowhere to be seen.
"Where is she?"
As if being summoned, you appeared behind them in the doorway and if not for being seasoned officers of the law, they all would've jumped, well, Adam did but that's beside the point.
"Hey, you guys made it just in time! So sorry if you were waiting long, I was just in the restroom. There's some last-minute things I want to go over that I didn't get to last time. Klein's lawyer submitted some evidence, and I just want some clarification."
You spoke as they all stepped aside, allowing you to make your way to your desk that was the definition of an organised mess.
Your heels thudded against the carpet, the bottoms red and the heels still ever so high. Your trousers had not a single crease, the legs were wide at the bottom, but they fit you perfectly. Your blazer sat on the back of your chair and your shirt wasn't the usual style she was used to seeing you wear.
It was long-sleeved and a little bit bigger, it was tied in a neat bow around your stoma-
Your stomach was round.
It wasn't too noticeable, but when you turned sideways to pick up a different folder, she could see your stomach was rounder. In fact, the way your shirt was tied, it was all clicking into place, the shirt suspiciously similar to maternity clothes.
Kim tried to focus on what you were saying but found herself unable to look away. It felt rude to ask because it could just be that you gained weight, it happened to everyone! And the last thing she wanted was to offend you or distract anyone before they were due to be in court for a case that had to go their way.
And so Kim bit her tongue, exchanges looks with Adam when she realised he had also seen what she saw but said man just shook his head frantically.
On their way to the courtroom, Kim overheard a fraction of your conversation with Jay.
"It was just my morning sickness but it's definitely better than the first trimester-"
After hearing that, she decided to block out the rest of your conversation and zero in on what Adam was saying to Kevin.
In the courtroom, you were your usual confident self. After the first round of questioning, you had unbuttoned your blazer and took it off, placing it on the empty chair besides you and no one but the opposing sides lawyer batted an eye.
The lawyer seemed stunned, steps to the stand faltering before he quickly recovered and went back like nothing had happened.
Apparently he hadn't seen many pregnant lawyers in court or maybe he hadn't expected that you, of all the lawyers he knew, would be pregnant.
Recess was quick and the verdict even quicker.
Smiling, more than satisfied with the sentencing the judge determined, you packed up your things and smugly shook the other lawyerâs hands before striding off, the sound of your heels lost in the now loud courtroom.
You walked up to Jay who took your blazer and draped it over his arm as the two of you walked out side by side, the gap between your shoulders basically non-existent and his hand only found the small of your back once you made it a few steps away from the doors.
Kim didn't have to think too hard for all the puzzle pieces over the years to all click perfectly into place.
Laughing to herself, she shook off Adam's questioning gaze as she watched the two of you walk away, your blazer on Jay's arm and your Birkin in his hand with your hand looped through his other arm.
You were the picturesque image on badass wife and completely smitten husband.
With your heels clicking off into the distance, Jay's small but clear as day adoring smile on his face as he listened to you talking his ear off, your words of ultrasound the last thing she heard as you both left the courthouse.
If Kim were a better person, she wouldn't be thinking of the betting pool that no one had been able to cash in on since your engagement almost four years ago.
But she wasn't a better person and now she somehow had to get in contact with Antonio. They were a little too late to pay for Eva's college tuition but maybe they could be for Diegoâs.















