It was a normal day for Hailey. She woke up, got ready and then drove to work. When she got to the district, she buzzed herself up and met up with Jay to talk about the double murder they'd gotten this morning. Not too long after Jay and Hailey had started talking about the case, Trudy comes up. She hands Hailey a few packages and then Trudy pulls Hailey aside, "The feds have been sending packages. I don't know what you're going to do with them, but they clearly don't want to wait long for a decision." Trudy tells her. "Do you know what the offer is?" Hailey replies. "No, but when you find out, think carefully. Halstead has already lost one partner to the FBI and I think he'd be lost if he lost you too. I don't want your decision to be based on what Halstead thinks, but you do need to think about how it will effect him... how it will effect all of us." Trudy says.
Hailey opens the packages, the offer is a once in a lifetime opportunity, it's something she'll never get offered again. She reads the pages, but in the back of her mind she hears Trudy saying "I think he'd be lost if he lost you too". Hailey thinks hesitatingly about weather or not she should tell Jay about the offer, but she ultimately decides not to tell him. They continue on with their day, Jay still curious as to what was in the packages. He had a feeling that the feds wanted her, but he didn't want to make any assumptions.
They eventually had a suspect for the murders and the ride over was the quietest ride they've had since Hailey and Jay first met. Jay finally breaks the silence and asks "Who were the packages from?". "The packages were from the feds, they just can't get enough of me." Hailey replies teasingly. Jay not knowing what to say, just turns and continues driving. They eventually got their suspect and brought him down to the district for questioning. Turns out they had the right guy. After they handed him off Hailey turns to Jay and asks "Want to go for drinks? It was a kind of rough day and you've been pretty quiet. I know you don't want to talk about this, but we're going to have to talk at some point." Jay agrees to go, knowing no matter how this ends, he'll be happy for her.
They decide to go to The Eagles Paradise, a bar that's far from their normal Molly's because they didn't want to run into anyone and they knew the team was going drinking, as they normally would after a case like this. Jay and Hailey sit down at a table and get a couple beers, they make small talk for a bit until Jay finally says "What'd the FBI offer you?" Hailey looks stunned at Jay, not expecting him to ask it so blatantly. "They offered me a joint-level task force." She replies. "So, you'd still be out on the field? We all know you could never sit at a desk, it would drive you insane." Jay says.
They sit there for a little while longer not saying much of anything to each other when Jay asks "So, are you going to take it?". Hailey sits there thinking for a minute, not entirely sure how to respond to the question. She knows it's not a question that can be answered that quickly, and he knows that too, but he asked anyways. "I don't know yet. I haven't thought about it enough to make a decision. It's not really a decision I can make over night. I mean I'd be moving to New York and I'd be leaving Chicago for good." Hailey says to Jay who's starting to look upset. He knew she was offered a job with the FBI, but hearing her say all that? It was different, if she took this job, he'd lose her. He'd lose another partner. He'd gotten over losing Erin, but he's not sure he could ever get over losing Hailey. They had a connection that he'd never had with Erin, she understood him and constantly helped him be the best he could be. So, hearing her say if she took it she'd be leaving Chicago... and him? He didn't know what to say, he would never be ready to lose her, but he wants her to be happy. "I think I'm going to head home, I need to sleep" Jay says to her. He doesn't actually need to sleep. In fact he's not even tired, but he needs time to think. Time to think where Hailey isn't in front of him. Time to think what will happen if he loses her. He has so much to think about and she has a decision to make so soon. He wants to be happy for her, but he doesn't know if he can be if it involves losing her for good.
Hailey turns to Jay and says "Jay, before you go. You know, you could tell me you don't want me to take it." "Tell you not to take what?" Jay replies stunned, even though he knows exactly what she wants him to tell her. "You can tell me that you don't want ne to take the job with the FBI. You can tell me you don't want me to leave Chicago. You can tell me you don't want me to leave you." She says to him, with hope in her eyes. "I can tell you not to leave, or you can tell me what you were going to tell me in the hospital after I got shot." He says to her. "Jay, do you really want to know what I was going to tell you?" She replies. "I wouldn't of asked if I didn't want to know. If I'm still hanging onto it after it's been over a year, I obviously really want to know what you were going to say. Hailey, tell me something that will convince me to tell you to not take the job. I want to tell you to take it if it's what you want, but you want me to tell you not to take it. So, tell me something that will convince me to tell you not to take it." He says. Hailey turns to him once again and goes "I wanted to tell you that I loved you, but then the phone rang and I figured it was just... I don't know. Maybe it wasn't the right time. I think maybe I was right with that, maybe your phone ringing really did mean it wasn't the right time because here I am, giving you a reason to tell me not to take the job with the FBI. I am standing here, giving you a reason to tell me to not take the next flight to New York and accept the job offer." Jay looks at Hailey stunned. He wasn't expecting her to say that, he knew what she was going to say at the hospital wasn't going to be anything simple, but now that she's said this it changes everything. He looks at her shocked and says "Wow Hails, I- I wasn't expecting all that. I was only going to tell you to take the job if it was something you truly wanted, I'd never want to stand in the way of you and getting the job you truly want. I mean I'd miss getting to see you everyday, I'd miss being your partner, I'd miss your smile and your laugh. But I didn't want to stop you from leaving. Hailey... I've felt the same way for a long time, but never wanted to say anything because I wasn't sure how you felt. Now I know, so here I am telling you I don't want you to take it. I don't want you to move to New York, I don't want to never see you again." She smiles knowing exactly what comes next.
Jay stands back up and pulls her in for a kiss. He's dreamed about this hundreds of times, but he never actually expected to ever get to kiss her. She's finally got what she wanted, even though she definitely didn't expect it to start this way. If it wasn't for Vanessa she would've never even accepted the fact that she had feelings for him. That day when she went to tell him and he got the phone call, that was it. She thought she'd never get to tell him. She thought they just weren't meant to be. But here she is a year later, his lips on hers. Holding into him like she'll never let him go because well, the truth is she never does want to let him go. She eventually pulls away and they go back to her house. They just lay there quietly, her head on his chest. She can hear his soft heartbeat. He's playing with her long blonde hair that's now tangled from her day at work. To think that all that was needed to get here was a job offer they both wished they would've tried to get one sooner. They spent the night together, doing nothing except holding each other. They both eventually fell asleep for the night, still holding onto each other with the feeling of never wanting to let go. He'll never regret telling her to not take it that day because it finally gave them their chance. Their chance to be together.