Hailey Upton, Jay Halstead, and Antonio Dawson were going to be sent on an undercover mission in a ritzy nightclub. Antonio was going to pose as a bartender in one of the private rooms, while Jay and Hailey were going in as an upscale couple. Normally such a task wouldn't be given much thought by them, but things between Jay & Hailey have been a little awkward recently, to say the least. It all started a few months ago when Hailey and Adam broke up, coinciding around the time Kim found out about them. Hailey had assumed things would go back to normal with her and Jay after this, but she was wrong. Not to say things had been bad between them, but it had definitely felt like something was brewing beneath the surface while she was sleeping with Adam. Putting a stop to that didn't seem to fix things, unfortunately. She was at a loss, while Jay went on pretending that nothing was wrong.

They were still at the precinct and getting in to "character," Kim debating the best way to secure a wire under Hailey's dress, or whether or not they should, when Jay walked in already in his suit. Jay was wowed by how good Hailey looked, and he quickly tried to hide his reaction by blanking his face; not before locking eyes with Hailey though. The moment lasting no more than a couple of seconds, like so many of their electric looks over the past two years, and especially over the past few months, but both quickly looked away once Kim spoke.

"Oh good Jay, you're just in time to help us decide… this style of dress isn't really conducive to wearing a wire without it being seen. Do you think we should give Hailey something else, or will you guys be good?" Kim asked.

"I was actually just discussing this with Antonio. He's going to be the most wired, since he'll probably be seeing more things than us, and no one will get close to him since he'll be behind the bar. And then I'll have a cell phone tapped to speak into if necessary, so we can do the same with Hailey I guess? We'll always be together, but just to be safe in the off chance we're separated."

"Yea, that sounds good because as you can tell, there's not much room for hiding in this dress! You rock it girl!" she teases and gets thrown a dirty look from Hailey. Jay looks away uncomfortably.

"Enjoy this while you can Kim, cause next undercover case I'm recommending you to Voight." Hailey jokes. "But I like the phone idea, I'll just keep it in my clutch."

"Great, I'll go get one and have them set it up for you." Kim walks out, leaving Hailey and Jay standing around awkwardly.

Jay is the first to break the silence, "So this assignment should hopefully be easy, we'll just have to be extra eyes for Antonio."

Hailey nods and gives him a small smile, "Yea."

Jay locks eyes with her again and hesitantly says, "The dress looks good on you, by the way."

"Thanks! You clean up pretty nicely yourself." She finishes saying as Kim walks back in.

"Ok guys, we're all set! Here are the phones, so ready when you are."

"Great, let's get this over with, I'm already uncomfortable in this outfit." Hailey jokes as all three of them walk out together.


Antonio, Jay, and Hailey have been at the club for a couple of hours now. Antonio has been busy making drinks for the few patrons in the small room, while Jay and Hailey have been hanging by the bar pretending to be drinking. They're waiting on a high-end pimp who runs an escort service, or for any of his clients or girls. There hasn't been much sign of anything yet, so they just keep on as their undercover egos.

Throughout the night, both Jay and Hailey glance at the other longingly when one of them isn't paying attention. Neither of them would dare admit it of course, but it's selling their cover quite nicely to those around them. Hailey has been grappling with her feelings for Jay for quite a while, since before he was shot, but she's done her best to bury them as much as possible. Her situation with Adam had helped for a while, but she knew it was only a temporary solution. Once Kim had found out, she figured it was the best excuse to cut ties, and she almost believed it herself. She wanted her dynamic with Jay to return, and to her dismay, the tension is still there.

The tension is actually still there because it took Jay catching her with Adam, to realize he had feelings for her himself. He had tried to assure Hailey that things were fine between them, but jealousy would overwhelm him anytime he heard Adam's name. He didn't know what to do because Hailey was his partner and friend, and he didn't want to destroy that. An immense relief washed over him when Hailey told him her and Adam were done because he figured he'd return to feeling normal about her again… but he was wrong. His feelings for her had become even stronger, and he was running out of ways & ideas to hide them. Any time they had a drink after a case now, they both felt something simmering beneath the surface between them, but neither of them knew how to address it, or if they should.

Their thoughts were interrupted when Antonio walked back over to their side of the bar.

"You guys haven't noticed anything yet right?" he asks them.

"No, nothing," Jay responds.

"Hmm, alright, well, it's still early yet. I'm sure something will turn up later in the night." He grabs Jay's drink and makes him another non-alcoholic one with the fake rum bottle they brought, then walks away leaving them alone again.

"Early? It's 11:30, how much later can they arrive? Am I that old already?" Hailey asks while smirking, but slightly annoyed.

"Nah, you're right, this should be prime bar time… if you're pushing 40." Jay jokes with her and Hailey gives him her eye roll.

"You're an ass sometimes, Halstead. Have I told you that yet today? Because I should have!.. And don't you dare call me 40 again!" she says as she pokes the cherry in her drink with the toothpick sword and pops it into her mouth, clearly trying to mockingly mean business.

Jay laughs, and they both notice Antonio turn around to give them the death stare. Both of them crack up when they realize he heard them making fun of forty-somethings.

"Sorry Antonio!" Jay mutters into his phone. "Yea, sorry," Hailey concurs. "Jay started it though; he's just trying to deflect being the true grandpa of the unit!" Jay gives her a look, but smiles at her and she smiles back. It's a moment that feels like old times for them and both of them are enjoying relishing in it.

Another hour goes by while Hailey and Jay wait patiently making small talk. They're both enjoying themselves and have almost forgotten they're on assignment. It's then that a guy starts to pass by the small room and looks inside when Jay freezes.

"Shit! I know that guy, I'm gonna get made!"

"What? Who?" Hailey says as she starts to look around.

"Kiss me!"

"Whaa…" Hailey is perplexed and in midst of saying when Jay leans in and kisses her, silencing the confused question.

Jay is equally in shock that kissing Hailey is the route he chose to not be recognized, but there's a small part of his subconscious that's glad he did. At first, Hailey doesn't know how to react, but after a few seconds she finds herself relaxing and actually kissing him back. This equally surprises Jay, but he's ecstatic over it. Soon enough, the two forget where they are and why they started kissing in the first place. They don't even notice that the guy Jay knew ended up not even entering the room. The kiss goes on for at least a couple of minutes when finally Antonio walks back over to them and simply, but loudly coughs. Jay and Hailey instantly pull apart and tense up, staring at the other. Antonio gives them a strange, but knowing look and walks away again.

They both put their hands to their mouths and have no idea what to say. Both realizing what a pivotal moment in their relationship this is, and realizing that it meant more than they're going to admit. They both look down at the bar, avoiding eye contact, catching their breathe, and fighting to admit the fact they'd like it to happen again.

Jay finally speaks up, "Well, at least we didn't lose our cover."

Hailey slowing looks back up at him, biting her lip, all she can manage is, "Yeah."

It's pushing 1am now and they're glad that either way this night should be over soon. Both wanting to run as far away from the other as possible… hoping that their feelings will run far away with them…


[A/N: Sorry for the slight cliffhanger, I will add to and epilogue this story soon. Just an idea that popped into my head; would love something like this forcing Jay & Hailey to let their guard down in the show. Hopefully one day soon! Thanks for all the love you guys have shown me!]