A/N: Hi,
This was actually the first Upstead fic I've ever published (it was published on AO3 a while ago, I'm only now uploading all my work to ffnet.). I hope I captured these characters well enough. And they come close enough to the characters you know and love. Anyway, this fic just came to me as I was talking with my friends about Upstead, and I decided to write it down. It's pretty short, but it's meant to be that way, light and fun.
Before you start reading, it's important to know that this fic takes place AFTER 8x03/8x04, but BEFORE everyone finds out about Upstead officially dating.
I'd like to thank the gc, for helping me come up with this idea, as well as encouraging me to write it. Special thank you to Hattie, Maddie and Beth, for helping me come up with some of these ideas. And another shoutout to Dynn and especially upjamisforever who beta read this story for me and helped me bring it to life even more.
Come find me on Twitter under mrsavalance, and talk all things Upstead with me?
Anyway, I hope you enjoy reading this. And maybe if you have a few seconds, leave a review in the comments? I love hearing back from you guys!
Enjoy!
Prompt: Five times Sergeant Platt likes to tease Upstead about their newfound and supposedly unknown relationship (that they haven't told anyone about yet) until one day Hailey exacts her revenge.
1.
"You sure it'll be okay?" Detective Jay Halstead nervously pleads with his partner, best friend, and now girlfriend Detective Hailey Upton as they gather their things from his truck for another surely busy workday ahead.
"Jay, you need to lighten up." Hailey answers as she playfully shoves him in the middle of the parking lot, causing him to grin. God, she loved his smile. And she loved being the reason for his genuine happiness even more.
"Stop trying to distract me!" Jay retorts as he adjusts the duffel bag on his shoulder.
"You didn't complain about me 'distracting' you last night… or this morning, for that matter." She implies suggestively.
Jay's eyes go wide. "Hailey!" He shushes while frantically looking around to see if anyone heard what she just said as they near the main entrance to the 21st District. He visibly relaxes when he realizes none of their colleagues are within earshot before adding, "I'm serious, though."
She keeps laughing as she continues, "Oh, come on, Jay. It's just a T-shirt. Plus, your jacket almost completely covers it, so no one's even gonna catch it."
"Hailey, you know as well as I do that we work with some of the most elite cops out there, so they're definitely gonna notice and put it together." Jay says as he clearly cannot let this go.
"Just change before you get to your desk, and it'll be fine," Hailey advises, a final attempt to reassure her boyfriend before opening the door and stepping into their bustling workplace.
"Good morning, Sarge." Hailey greets Sergeant Trudy Platt with her usual welcoming smile as the detective duo approach with Jay by her side, uncharacteristically aloof.
"Morning, Upton... Halstead." Platt responds, glancing between the partners as they sign in at the front desk with a small grin forming on her face.
There's just something different about them this morning. An extra spring in their step, a certain glow about them. Trudy didn't have to be a decorated cop to pick up on what changed between them. The grin on her face grows into her famous wicked one. Oh, she is definitely going to poke some fun at these two.
"Have a good day, you two." Trudy quips before the two detectives step away to head upstairs to Intelligence, ready to start their workday.
"You too, Sergeant." Hailey beams back as they turn and walk toward the stairs.
"Oh, and Halstead..." Jay turns around to face Platt again when he hears his surname. "Nice shirt. You looked good in it yesterday, still looks good today."
Jay freezes as his face becomes tomato red. If the ground could swallow him, now would be the perfect time to consume him. He's absolutely mortified. He knew he should've gone home before coming into work today, but then Hailey distracted him again this morning, so they had run out of time to stop by his place for him to properly change.
After partially regaining his bearings, Jay shifts his focus to Hailey, who is trying her hardest to look sorry but cannot contain how much she is enjoying this moment.
"This is so your fault." Jay forcefully whispers through his teeth when he catches up to her halfway up the stairs.
Hailey can't stop the small chuckle from escaping her as she bypasses the security lock to open the gate for them, and Jay gives her a death glare as he walks through.
"I don't like you right now." Jay says low enough for only Hailey to hear as they make their way into the bullpen.
Hailey just raises her eyebrow at him, challenging him to prove it. Because if last night and this morning were any indication, she'd say he likes her just fine, loves her even.
2.
Trudy quietly climbs the stairs up to Intelligence, observing Jay as he briefs the team about their newest case. The unit's boss Sergeant Hank Voight is stuck in an obligatory meeting at the Ivory Tower and has put the squad's senior member in charge for the day.
Platt knows that Voight has been grooming Halstead to take over the unit for him one day; she's just not sure if Jay's aware that today is essentially a test run for that eventuality. Judging from the way the charismatic detective is naturally commanding the room in front of the famous whiteboard, Trudy has no doubt that he'll continue to make her and Voight proud as an excellent and upstanding boss someday.
After watching him grow into his own over all these years, she can't help but feel pride for Jay, who is now wrapping up the meeting. "Atwater, Burgess, you two go pick up Ricardo Diaz. Ruzek, talk to your CI, see what else you can find out about this deal gone awry. Hailey and I will run point from here."
The younger trio of officers all give their various forms of acknowledgement to their fill-in leader before scrambling out of the bullpen, leaving the detective partners and desk sergeant behind.
"Sergeant Platt." Jay greets.
"Detective." Trudy returns politely. "Came to see if you needed any help, but it looks like you got things under control around here."
"Yeah, Hailey and I got it figured out, I believe." Jay notices the subtle but proud smile spreading across his girlfriend's lips from where she's seated atop her desk.
"Hailey, huh?" Platt teases lightly.
"Uh, yeah?" Jay looks genuinely confused. "Something wrong with that?"
"Oh, it's nothing… just you almost exclusively call everyone by their last name, except for Upton here." Trudy retorts triumphantly.
Embarrassed once again, Jay freezes like a deer in headlights before he desperately seeks out Hailey's eyes for assistance in this incredibly awkward moment. The partners both look like they have been caught with their hands in the cookie jar. Platt wishes she could take a picture of this shared gaze and tease them about it some more later, but she mercifully decides to let the opportunity pass.
After an extended pause, Jay seems to recover from his initial state of panic. "Well, she is my partner."
"And Hailey is my name." Hailey continues.
Trudy shifts her gaze between the detectives. "You two really are something else."
"Uh, thanks? I guess." Hailey replies uneasily, her eyes once again landing on her boyfriend, who appears just as confused.
"Get back to work, you two. Those bad guys aren't going to catch themselves." Trudy orders as she turns to return to her post at the front desk.
"Copy that." Jay acknowledges.
"Copy you." Hailey follows.
3.
"Hello there, Detective Chuckles."
"Sergeant Platt." Jay responds with his signature smile.
"To what do I owe the pleasure? Did you lose your car keys... again?"
"That was ONE time and EIGHT years ago, Sarge." Jay groans at the memory.
"And may you never forget the pile of paperwork I had to do for that tiny slip up of yours."
"I've apologized for that like a billion times since then; I even did your dry cleaning for an entire month."
"Alright, alright." Trudy waves him off before restarting the interaction. "So what can I help you with today?"
Jay sheepishly continues. "May I put in a request for some more pens?"
"You came all the way down here because your pens need to be restocked?" Trudy replies in disbelief.
"Yeah, uh... you're the one in charge of our inventory, right?" Jay asks, seemingly becoming more nervous with each passing second.
"I am, and you already know that because you had this same inquiry only a mere two months ago." The desk sergeant glares at the detective.
Now even more unsure of himself, Jay begins to scratch the back of his head to stall a bit as he attempts to come up with an inconspicuous response.
"What are you planning to do with all these new pens, Detective?" Trudy says, almost like she's challenging him, making him even more uneasy.
"Uh, someone's been- someone's been stealing mine from my desk." Jay finally admits.
Platt keeps digging into his suspicious story. "So… what you're telling me is you're a gifted detective, yet someone's been stealing your pens... for months now?"
As those words leave Sergeant Platt's mouth, Hailey makes her way down the stairs from Intelligence; her boyfriend's wary eyes lock with her baby blues before returning to Trudy. "Uh, maybe?"
"Are you asking or telling me, Halstead?" Trudy pries.
Jay just shrugs his shoulders, knowing that words can no longer help him wiggle out of this mess.
"Sounds like you should have someone look into the case of all these missing pens." Platt suggests mischievously. "If only you knew a detective who could solve such a serious matter."
"Jay, Voight wants us back at the crime scene to question a few more witnesses who just came forward." Hailey interjects into the obviously uncomfortable situation.
Trudy's eyes wander to Hailey, a grin breaking out on her face.
"Guess she's been stealing more than just your heart, huh, Halstead?" Trudy mutters under her breath, loud enough for only Jay to hear as he turns toward his partner holding open the district's front door for them.
Jay freezes in his tracks, horrified by the implication from the all-knowing (or omniscient) patrol sergeant of District 21.
"Hey, Jay." His girlfriend's voice snaps him out of his own distressed thoughts. "Let's roll."
"Right. Copy that." Jay says before quickly making his way out the door.
4.
Trudy walks past the district locker room, hearing two hushed voices coming from the other side of the door. She's unable to make out what they're saying and peeks through the slight opening to find Halstead and Upton standing between the rows of lockers, sharing what seems to be a pretty intense conversation.
They are both fully dressed, and to any other passerby would probably come across as a pair of dedicated professionals clearing the air about some disagreement that arose during a tough case.
Trudy Platt, however, is not just anyone walking around the 21st; today has kind of been a slow day for her, so she easily convinces herself that she deserves to have some fun before loudly banging on the door, startling Jay and Hailey to jump apart.
"What the-" Hailey curses.
"Are you guys decent?" Platt's voice rings into the tense air.
Jay looks at his girlfriend in confusion, the blonde just shrugs her shoulders.
"Uh, yeah... Why wouldn't we be?" Jay calls back.
Trudy slowly pushes the ajar door fully open to join the two lovebirds, now standing with much more distance between them.
"Oh, Halstead, you don't even wanna imagine half the things I've walked in on in this locker room over the years. I still need therapy after the last time." The sergeant enlightens the detective duo.
"Should we ask about 'last time'?" Hailey whispers under her breath to her boyfriend.
"I'd rather not." Jay mumbles in response.
"I'd rather you'd not." Trudy reinforces, shivering at the seemingly fresh memory. "Let's just say Burgess and Ruzek have a 'nothing behind closed doors at work' policy now."
5.
"Hey, Detective Chuckles, I need you to fill out these forms for me. Mrs. Chuckles, you too." Trudy calls out to Halstead and Upton respectively, who just walked back into the district from a crime scene.
"Copy that, Sarge." Jay acknowledges before walking over with Hailey and taking the forms from the desk sergeant.
While walking back up to the bullpen, Hailey looks back at Platt before refocusing on Jay. "Did she really just call me Mrs. Chuckles?"
"I think she did." Jay grins.
"Why on Earth… How are you not more freaked out by this?" Hailey questions him.
"It's not like it's the first time, though." The mischievous look Jay gives his girlfriend, believing they are on the same page, but she still looks lost.
"What do you mean it's not the first time?" Hailey's voice cracks into a higher octave than normal.
"She's called you Mrs. Chuckles before." Jay reaffirms.
"No, she hasn't." Hailey argues back. "Not to my face, anyway."
"Oh..."
"Oh?" Hailey glares incredulously at her partner, who is punching in his code to unlock the security gate. "Care to fill me in?"
"Okay, so last week when you were stuck in court, she may have asked me where Mrs. Chuckles was." Jay explains hesitantly.
Hailey jabs his shoulder. "And you're just telling me this now?!"
"I thought you knew!" Jay tries to justify.
"Well, clearly, I didn't!" Hailey retorts.
"Clearly..." Jay sighs, knowing that their conversation is echoing throughout the district more than they would like it to.
"What?" Hailey asks after a brief silence, noticing the smile finally breaking through on her boyfriend's face.
"Nothing. It's just… Mrs. Chuckles has a nice ring to it." Jay softly admits.
The look his hopeful eyes give her grounds her and makes all the tension about Platt knowing about them evaporate from her body. "Yeah, I guess it does."
Bonus:
"Upton, is that a burn on your neck?" Trudy asks, sounding concerned, but the hint of a smile on her face gives away her true intentions for anyone paying attention.
Hailey's hand instinctively raises to cover her neck. "Uh..."
"Did you hurt yourself with a curling iron this morning? Because you should really put some aloe on that." The wise desk sergeant advises.
Standing beside his girlfriend, Jay is trying his hardest to bite his tongue and not burst out into laughter before the urge becomes too much, his soft chuckles making their entrance known.
"Oh, screw you, Halstead." Hailey quips mischievously while glaring at her boyfriend.
Jay's eyes immediately grow wide. She wouldn't.
"Actually, Sarge, you can thank our favorite Detective Chuckles over there for this." Hailey flatly states, gesturing to the giant hickey Jay so proudly gave her overnight.
Jay's face gets all flushed as he glances between Hailey and Trudy in disbelief, his partner really just said that aloud and to Platt of all people.
"Oh, come on, you knew exactly what you were doing. If I have to do the walk of shame, so do you." Hailey continues down her warpath. And if Trudy's eyes weren't wide already, that comment would have definitely done the trick. She just stands there, stunned into silence, shifting her gaze between the detective partners, her mouth slightly agape.
"I think we broke Platt." Hailey whispers softly to Jay, her signature grin coming to life.
"I think so, too." Jay laughs back.