Hello all! Thanks for giving this little fic a read! It is my first one for this fandom (which I am completely and utterly obsessed with) so I would appreciate your thoughts! I have some ideas for future holiday one-shots that will follow this one, so stay tuned!

Much thanks and happy holidays!


"Hey Goldilocks, come here for a second."

Hailey glances up from the files she is reading and by the look on the Sargent's face, she certainly should have let Kevin run this folder down to record-keeping. She sighs, closing the manila folder and making her way to the desk.

"What's up Sarge?" She rests her arms on the desk, raising herself slightly on her toes and leaning forward.

"Who are you bringing to the holiday party? I'm trying to get a headcount." Platt says matter of factly, barely even looking at the detective while she speaks, instead busying herself with some papers in front of her.

"Myself?" Hailey says slowly as if she is not sure it is the correct answer.

Platt gives her that look, pulling her attention from the papers to Hailey. "I meant who are you bringing at your date.

"I'm not bringing any-"

"You have to bring a date." Platt cuts her off.

"I went by myself last year." Hailey shoots Platt a confused look, but the older woman doesn't bite.

"It's not last year now is it. I'm trying to look out for you all upstairs. I can't have all the members of Intelligence dying alone because they decided to spend every waking minute in that bullpen." Platt tells her and Hailey swears she will never quite figure this woman out.

"I'll be having this conversation with Jay and Kevin too," Platt adds.

"Why not Kim and Adam?" Hailey asks and she is once again rewarded with one of Platt's did you really just say that? faces.

"I'm not a monster, Hailey." The tone of her voice almost sounds offended and Hailey really wishes she had asked Kevin to run these papers downstairs because this conversation continues to derail off of the tracks. "Besides, I promise you they'll both get as drunk as they did last year and they'll go home together. They don't need my help."

"But I do?"

"Oh dear, you have no idea."


"Have I mentioned that I hate the cold?" Hailey huffs, a small puff of freezing air coming from her mouth.

"Not in the last five minutes." Jay teases and she rolls her eyes at him. They are sitting in the back of the van, doing surveillance on the latest of criminals who they've had the fortune of crossing paths with. She understands that crime does not take a break for the holidays, but damn if they could at least get an interesting case because this one is shaping up to be a boring bust, thus allowing for their small talk in the back of the van.

"The normal cold, I'm fine with." Hailey continues. "But it's literally too cold to snow. Too cold to snow. What type of Antarctic city do we live in?"

"You could go back to New York." He says softly and she stops herself from rolling her eyes again because that will just earn her another smart comment from Jay.

She has been back from New York for a few months and the first few weeks back her chaos to say the least. Vanessa left for an undercover assignment and yet another change in the team led to having to regroup yet again. Not to mention all the chaos that was 2020 and having to try to serve the city during that. But Jay was her constant through it all. They had certainly become closer after her return to the windy city. During her time away, they had spent much time texting and Facetiming and their flirty banter only continued when she came home. Neither one of them was exactly discreet about their attraction for the other, but neither had been bold enough to take that next step.

"And deprive myself of the opportunity to freeze my ass off in the back of your van?" She smiles. "Hell no."

He doesn't say anything, just flashes her a typical Jay smile, and she swears she has to will her heart to stop beating faster when he looks at her that way.

"You looking forward to the holiday party tomorrow?" He changes the subject and the question is not even out of his mouth before Hailey starts groaning. He laughs, saying "Wow I knew you weren't a holiday person, but wow. At least last year you were on board for the free booze."

"Last year Platt wasn't on my ass about bringing a date." Hailey quips back.

"Really?" Jay says as he stretches in his seat. They've been sitting in this van for three hours doing surveillance and still have nothing. She is surprised he is still able to sit still.

"Don't laugh. She told me she is coming for you next. Something about making sure all of intelligence doesn't die alone."

Jay shakes his head. "Something tells me she is going to leave Adam and Kim alone though?"

Hailey smiles. "She said they could figure themselves out. She thinks they'll get drunk and leave together."

"Probably." Jay hums and Hailey thinks back to the last holiday party, with Kim's slurred words and Adam's one to many drunken shouts of "Merry Christmas Chicago!" A smile curls on her lips at the thought and she is brought back to reality when Jay says "But she's got no such hope for us?"

The layered meaning of Jay's words is not lost on her, but she decides the back of the van while they are doing surveillance and she is so cold she truly believes her hands might fall off might just not be the place for that conversation.

"Apparently not. She told me she will find someone to set me up with and that is just punishment that I do not need."

"We could just tell Platt we're going together." He offers up casually.

She doesn't answer at first, leaning closer to the window, grasping the camera in her hand, thinking maybe she can will their suspect to make an appearance at this moment to avoid whatever conversation she and her partner are about to have. She releases a heavy sigh, knowing their day is a bust and there is no way they will be seeing anything resembling action any time soon.

"So that's your plan to get them off our backs?" She finally says. "For a detective, you're not that smart."

He smirks at her joke. "Just saying if it's between Platt trying to set me up or her giving me a hard time for going with you, I'll go with the latter."

Hailey lets out a laugh and tries to avoid the burning red that is rising in her cheeks. "I would take that as a compliment but I know you are just genuinely terrified of who Platt would set you up with."

"Hails, you know I'd always choose you." He says honestly and when she gives him a small, but questioning smile, he adds. "But yeah, the less Platt interferes with my love life, the better."


It's decided. They will go together to the holiday party, for nothing more than to get Platt off of their backs. She convinces herself it's not a big deal because honestly they were basically going together, to begin with. He would have picked her up in his truck and they would have left together to head back to her place to have another beer and laugh about what antics the rest of their coworkers caused during the night. Still, that fact in mind, she still felt the nervousness in her stomach at the thought of going to the holiday party with Jay.

His response to Platt when she brought up the party did not help either.

"Chuckles," Platt called out when the duo returned from their failed surveillance endeavor. Jay smirked at Hailey, before making his way to the desk sergeant while Hailey hung back.

"Sarge, we've been over this. It's Detective Chuckles, thank you very much."

Platt shoots him an unamused face and Hailey almost laughs watching the woman. "Okay, funny guy. I'm doing a final headcount and I need to know who you're bringing as your date. If you don't have someone, I will gladly call-"

"I'm going with Hailey." He cuts her off and Hailey can only imagine his face. However Platt was going to end that sentence, he certainly did not want to wait around long enough to find out.

"I know you two are joined at the hip, but I meant your date. It's like I told blondie, I'm trying to make sure you all don't die alone. And you seem to have an affinity for getting shot, so you need extra help."

"I know what you meant Sarge. I'm going with Hailey. I appreciate your concern, but I'm good."

Hailey sees Platt make a questioning face and she is not sure what look Jay gives her in return, but the woman stands down and finally says. "Good. You two better not be late."

The damn butterflies in her stomach come back again and when he turns around to look at her, a smug smile plastered on his face, she knows she is in trouble.


The music is loud in Molly's and the laughter is infectious. Hailey is nursing a beer and standing next to Kevin while they watch Adam and Jay play some dumb party game against Casey and Severide. As they watch their coworkers try (and utterly fail), she turns to Kevin and says "So, did you find someone to bring or is Platt setting you up with someone?"

Kevin scrunches his face in confusion. "Upton, what are you talking about?"

Hailey takes another drink of her beer. "Platt basically forced Jay and I to bring dates to this thing or she would set us up with people. She said she would do the same with you. Something about making sure the whole unit didn't die alone upstairs." She laughs.

"Platt didn't say anything to me."

Hailey lowers her drink. "You sure?"

Kevin chuckles. "Pretty sure. Y'all got played."

Hailey groans because, as a detective, she really should have caught on to Platt's little game a bit quicker. Platt did not say anything to Kevin because she was not concerned about them not all dying alone, but she wanted Jay and Hailey to wake the hell up. The duo had received a comment or twelve from the woman about the closeness of their relationship and apparently she no longer had the patience for the two of them to figure themselves out. It now made sense that she gave up fighting so easily when Jay said he was going to bring Hailey.

She was never going to set them up with other people at all. She was going to get them up with each other.

Damn that woman was good.

Party members start cheering and Hailey sees that the men of 51 had won whatever ridiculous game they were playing and are accepting high fives and hugs from their fellow fire-fighters. Adam and Jay start walking towards the table Kevin and Hailey are at and she takes that moment to grab Jay's arm and drag him towards a quieter corner of the bar.

"She played us. I can't believe we didn't realize what she was doing." Hailey mutters when they are standing by the door and out of earshot of their friends.

"What are you talking about?"

"Platt didn't talk to Kevin about bringing anyone," Hailey explains. "Just us." Jay's face is still riddled with confusion and she swears someone needs to take away one of their badges.

"She wanted this" Hailey motions between the two of them quickly. "She set us up and we fell for it."

Jay groans, realizing she is right. He glances to where Platt is sitting with Mouch and Voight and he knows he should have expected something like this because it's Platt.

"Do we say something or-"

"No" Jay turns back to Hailey and cuts her off. "She wants to mess with us, well two can play at that game."

"You have a death wish, don't you." Hailey rolls her eyes.

"She was worried about us dying alone. At least I know she will kill you too." There's that smirk again and Hailey knows it's probably not a good idea, but she's one too many drinks in to think clearly, and damn if she does not want to mess with Platt, even just a little.


The rest of the night, every time they were with Platt, they turned on the act. Hailey would lean into Jay's side a bit more than necessary, Jay would rest his hand on her shoulder or her back, and both would glance at the other, a knowing smirk in their eyes. They would touch more, laugh more, and flirt more than a typical day, but no one said anything about it. Kevin must have caught on to what they were doing because he doesn't say a word and just smirks at them when he goes to refill his drink. Kim and Adam are too far gone to notice the change in their workers' behavior, leaving Trudy Platt as the only one to make a comment.

"A little cozy, are we there detectives?" She says as they lean against the bar. Holiday karaoke is taking place and Hermann and Cruz are belting out an off-key rendition of "Let It Snow." Kevin is laughing at a table with Dr. Marcel and Adam and Kim are quietly chatting (or flirting) in a corner, leaving the partners alone with Platt.

Jay shrugs and Hailey can feel his body move against hers. His arm is around her shoulder and she is leaning against his back. Every now and then, he will rest his head against hers and watch their friends drunkenly sing another holiday song. A small smile rests on Hailey's face as she enjoys the entertainment and the closeness.

"Appears my work here is done." She states somewhat proudly and Hailey plays dumb, looking at Platt with a questioning face, but the older woman just stands up and says something about teaching the boys of House 51 how to hold their liquor before she disappears into the crowd.

Hailey glances up at Jay. "She's gonna be pissed when she finds out her plan did not actually work."

Jay laughs and he removes his arm from her shoulder. "She's going to pester us non-stop for the next month about this, just watch."

"You didn't think about that when you came up with this little plan, did you?" Hailey teases and she watches his eyes become serious.

"I did." He shrugs. "Just didn't care. It was worth it"

"If you wanted to put your arm around me, Halstead, you didn't need to make up some excuse of trying to trick Platt." Hailey laughs softly and the warmth in her cheeks grows. It's a dangerous line they are walking but blame it on Platt or the alcohol.

"Oh really?" A cocky grin decorates his face and his green eyes light up and Hailey can feel the return of those butterflies in her stomach. "Would you let me hold your hand or would I need an excuse for that?"

"Maybe. If you were really nice." Hailey smiles at him, and then casually glances up at the karaoke where Sylvia and Natalie and half singing half laughing their way through Jingle Bell Rock.

She returns her gaze to Jay and he doesn't move. His eyes are locked on her and he has a serious, low tone when he whispers "Would I need an excuse to kiss you?"

Hailey is taken back by his boldness and it takes her a second to collect her thoughts. She wants to tease him, to challenge him, to kiss him, but they are surrounded by their friends and coworkers, so she plays it safe. "That would really mess with Platt, wouldn't it?"

"What if I told you it wasn't to trick Platt?"

Hailey stares at him and sees no trace of teasing on his face. He is serious.

"I would say we should probably get out of here then."

Before Hailey can register what is happening, Jay has grabbed her hand and is leading her out of Molly's. Lucky for them, most of their friends are too drunk or busy or both to notice them leaving, together mind you. The minute they are through the door she feels the cold Chicago air, but that does not wake her up as much as Jay pulling her close and gently leaning her against the brick wall of the bar.

He pauses for a moment, just looking at her, and maybe it is the holiday spirit or the drinks (but it's probably the way that he is looking at her) that makes her say "You need an excuse to kiss me, or are you just going to do it?"

A devilish smile flashes on his face and before Hailey can register her thoughts, his lips are on hers and he kisses her. She grabs his jacket and pulls him closer to her, kissing him deeper. She is unsure of how many minutes they stand there like that, but it somehow feels like years yet seconds when he finally, tentatively pulls away from her and gently rests his forehead on hers.

"I've been looking for an excuse to do that for a while" He teases.

"Well, I guess now you don't need one." She says softly before raising herself up on her toes to kiss him again.

She thinks to herself, here in this moment, kissing her partner in the cold Chicago air outside their favorite bar, that maybe holiday miracles do happen, or at the very least, Platt is not a half-bad matchmaker. Not that she would ever admit it to her though.

(In fact, they don't tell her or anyone about their little secret for months. They spend their next few holidays celebrating secretly, with loving glances that their friends see, but do not understand. They do not tell anyone until a holiday party much like this one- a fourth of July barbeque filled with much laughter and too many drinks.

But that's another story.)


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