A/N: I'm so so happy with this chapter! It's a very Jay-centric one (though Chapter 6 will be Hailey based, so that's fair) and I really love how it turned out. We're finally getting some Halstead brother moments as well as some Jay/Adam time. Not much explicit Hailey/Jay but I hope you still love it! Thank you for reading!

"It's been way too long since we've done something like this. I can't believe I'm saying this, but I think I've missed your company," Will smirked, taking a sip of his beer.

Jay shook his head, amused. "Yeah, wish I could say the same."

In need of some time with his brother, Jay had called Will earlier that day and asked if he was free to come to Molly's later that night and, luckily, Will had been free and agreed to come and join him. It had, like Will said, been a little while since they'd hit up Molly's for a few drinks. Work had been crazy for the both of them, and with Will's almost-marriage and police drama, it hadn't even been an option for the two of them until now.

"How've you and the team been liking working outside in all this colder weather, huh?" Will raised an eyebrow. "I'll have you know that the ED is toasty warm."

Rolling his eyes, Jay took a swig of his own beer. "We've been in the station a lot lately. Only a few cases where we've had to leave the toasty warmth of our desks," he chuckled. "And I've been doing this for years, Will. This Chicago chill is nothing by this point."

Will laughed at his words.

"Anyway," Jay continued, sitting his beer down on the table in front of him. "Since we're catching up, it's only right I ask you about Nat. What's going on there? You haven't mentioned her once tonight."

The flash of pain that crossed Will's face was impossible to miss.

"Yeah, that's... done," he shrugged a shoulder and acted as if he wasn't particularly bothered by it, though Jay saw through that facade. "After the drama with that gun and everything... she gave the ring back. So if you want it to propose to someone, I guess it's yours now."

Jay frowned and gave Will a sympathetic look. "I'm sorry, man."

Will shook his head. "Don't be. It's my fault. I'm the one that kept putting her through all this shit," he sighed. "I guess I just wish that she could understand a little better that I'm the one that went through it all, too. I'm the one that saw it all first hand. Too late now, though."

He picked up his beer and took a long swig. He didn't want to get himself down tonight. Tonight was a good night – a night for him and Jay to spend time together and catch up. That's what it was.

"Enough about my troubles, though– I'm not engaged anymore, the ring's free. You got anyone you wanna propose to with it?" Will raised an eyebrow as he looked over at his brother, not expecting much in terms of an answer.

"Yeah, no– you keep it."

Will chuckled. "What's with the two of us and getting close to marriage but never getting there in the end? What's up with that?"

"It's some sort of Halstead curse," Jay joked. "Seriously, though. There's nothing going on even remotely romantic in my life right now, nor will there be for a while, I think. It's always ended badly for me. Might just have to give up on it entirely."

"And what about the Intelligence Unit, then? You were with Erin before, Kim was with Adam. Anyone else hooking up? You've gotta give me something to work with here, Jay."

Jay rolled his eyes. "Well Adam's with Hailey, now. And Kim knows."

Will seemed surprised by that – he hadn't expected to hear that Jay's partner was one of the people hooking up. Especially with Adam, of all people. And he knew Adam, he knew that he was a good guy, a solid guy, but he'd met Hailey, too, and Adam certainly didn't seem like her type. To him, at least. But he'd just ruined his engagement with Nat, so really, what did he know?

"Wait – Adam and Hailey? Your Hailey?"

"She's not my Hailey, Will," Jay scoffed. "And yeah, they're together. Kim found out the day the two of them got taken last week. She's been fine around them so far, so at least it's not awkward. I'm happy for her."

Will paused before replying. "You don't sound happy, Jay."

Jay raised his eyebrows and stopped still, staring at Will across the table. "You know, Hailey said the exact same thing a few nights ago."

It was pretty clear to Will what was going on here – Jay was jealous of Hailey's relationship with Adam. Maybe it was just because he didn't have anyone, or maybe it was because he cared too much about Hailey, or maybe it was something else... something more than that.

"Hear me out, Jay," he started. "But maybe you aren't as happy for her as you think you are... or maybe you're just saying you're happy for her because you're meant to be. You know what I mean?"

"Uhh, no–"

Before Jay could finish his sentence or Will could clarify what he meant, Connor Rhodes appeared at the table and gave them both a smile.

"Hey guys, I don't mean to interrupt, but is it all right if I just steal Will away for a second? Need to discuss something about a patient," he explained.

Jay nodded. "Yeah, yeah– of course," he stood up from his chair. "I might actually head home, get an early night. Big day tomorrow– but I'll call you tomorrow, yeah?"

It was clear that Will hadn't wanted the conversation to end there and that he had more to say but all he could do was agree with his brother and watch as he headed out of Molly's before talking to Connor.

"You all good, Kev?" Hailey asked, tugging her jacket closer to her as she got out of the car and crossed to where Kevin was standing on the sidewalk.

For Hailey's first undercover job after the beating, she'd chosen something small – infiltrating a party with Kevin to get one of the associates of the dealer they'd taken down a few nights ago. Her face was healing better now and in the dim lighting of the house, and with some make-up, the worst of it was well hidden.

"Yeah, let's do this," Kevin hummed, wrapping an arm around Hailey as they wandered up the stairs towards the house. Music was already blaring and it shook the stairs a little as they made their way towards the door.

Jay, from his spot in the van, shifted in his seat as he watched through the camera hidden in Kevin's jacket. This was just a simple undercover job, nothing too serious, but his heart was still beating fast in his chest as he watched them enter the party. He knew Hailey was going to be just fine. He'd seen her go undercover before. And Kevin was there if anything went wrong.

He'd been thinking about Will's words at Molly's the entire day and still hadn't really managed to decipher the meaning of them. Just saying he was happy for her? Not as happy for her as he thinks he is? It didn't make sense to him. He was happy for her. Hell, he was sitting in a van with the man that was making her happy right now.

Adam was watching as the two of them mingled at the party though he wasn't taking much of it in– instead, he was thinking about something he and Hailey had spoken about the other night, something that had been bugging him ever since they'd spoken. He'd been holding off about bringing it up with Jay ever since but it seemed his self control wasn't entirely there this time, and before he even knew it, he was blurting it out.

"Listen, man – I don't wanna overstep here, but the other night when I was with Hailey at her place, having drinks, I got thinking about something," he began, turning to look at Jay. "You're her partner. You know her better than anyone here, even me. And I think you should check in on her more. Especially after what happened."

While Jay had, initially, been intrigued about what Adam was going to say, the second he continued that intrigue disappeared. "I'm sorry, what?"

"She hasn't really spoken to me about what happened in that cabin with those men, even though I've told her she can. And I get that – I get that she wants to take it slow, and I'm cool with that. I'm just saying... you're her partner, you know? She's open with you. You need to be looking out for her. Especially when I can't be. I don't want her bottling all of this up inside just because she won't talk about it. As her partner, it's kind of your job to make sure she's not doing that."

Lost for words, Jay only stared at Adam for a few moments as he ran over his words in his head. It's his job to make sure she's not bottling things up? Sure. But he knows she's not. It's his job to be looking out for her– and he should be doing more of that? Adam was so... full of it.

He didn't think about his words before he said them.

"Mind your own business, man," he shook his head. "Hailey can handle herself just fine. She was doing it before you came along and she'll do it after. And what we talk or don't talk about while you're not around has nothing to do with you, so how about, instead of lecturing me about how I should be acting around my partner, you stop talking and do your job."