Jay wakes to a face he hasn't seen in 10 months, to the most beautiful face he's ever seen, even with her sparkling blue eyes red from obvious tears. It brings him equal amounts happiness and sadness. He wishes he could go back, he wishes he could make her happy again, but he knows it might be too late.

"Hailey! What are you doing here?" he manages to get out despite the severe cotton-mouth he's experiencing.

She leans back more in her chair next to his hospital bed, studying him silently; he knows she's pondering her words carefully like she always did back in the beginning. "You still have me as your emergency contact, so…"

"Hailey, I'm sorry, I just never thought to change it…"

"It's okay, I'm glad they called me." She smiles at him sadly.

"Me too, you're certainly the best looking thing I can imagine waking up to after this…" he tries to smile at her, but his lips are so dry he can feel them cracking and stops himself. She instantly notices and grabs him some ice chips.

"Jay, try not to exert yourself too much, please."

He nods as much as he can and they fall back into their old pattern of sitting quietly and harmoniously for a while, just glad to be by the other again despite the dreaded circumstances. During that time span, nurses and Dr. Lee all come in to check on Jay, all pleasantly surprised to see how well his body is recovering thus far. It's still going to be a long road, but Jay seems to be out of imminent danger at least.

Once they're alone again, Hailey starts to talk again. "I should go call Will, I doubt anyone has since I'm the one who was in your file… unless you think your current unit did?"

"No, probably not… but please don't, at least, not yet… I don't want him rushing in from Wisconsin when I'll be alright. Natalie and him are finally in a great place again and I don't want to disrupt that!"

"Jay, he's your brother! He has a right to know!"

"I know, and I'm not saying we won't tell him, let's just wait a day or two so he doesn't feel like he has to drop everything to be here. Besides, I'm sure he's over picking up after my messes anyway… I'm sorry that you have to even…"

"Jay…" she starts to say in her calm, disbelieving voice she only reserved for him, but stops herself. He knows she's contemplating her words again. "Alright, well, let me at least call Voight or…"

He cuts her off. "No, absolutely not, I'm sure he hates me. He has to blame me for losing two of his people. He could barely look at me when I asked him to sign the transfer papers for me to go back to Organized Crime."

"Jay, there's no way Voight could ever hate you. I'm sure he was disappointed when we left, but he knows what it's like. Besides, I'd like to at least see him while I'm here and the rest of the team…"

Jay doesn't want to have a discussion about the past right now, or the people he chose to leave behind because he couldn't let go of his pride, or sadness over her. So he does what he does best and tries to deflect. "Speaking of that, how long are you staying?"

"I don't know Jay, I literally just drove straight from Detroit the second I got the call, it's not like I had time or was thinking about updating my superiors. I'll call them in a bit."

"Yea, we wouldn't want the DEA missing you for too long…" Jay says glumly with a hint of snide.

Hailey sighs; at this point she may have actually preferred him still unconscious. "We're not doing this again, Jay, not now, not here… you know why I took it, we can play the blame game all day! I drove here because I still care, and I wanted to make sure you're ok, but if you're gonna be like this, I'll leave right now and I'll call Will on my way home!"

Jay mentally checks himself for being an ass. He thought he had gotten this all under control, but seeing her again just reminded him of all he lost due to his own stupidity. And she drove all the way here, fearing the worst about losing him, and this is how he treats her? His mom would have slapped him upside the head if she was still alive.

"You're right, I'm sorry… it's just, I've missed you and seeing you again is just bringing all the pain back. But please stay if you can, there's no one else I'd rather have here…"

He notices fresh tears start to well in her eyes before she evades his eyes and looks down at the floor. When she looks back up at him her emotions are already back under control. "It's ok, why don't we start over… how about you tell me about the case you had that put you in this hospital bed. What the hell happened?"

"I don't really remember fully to be honest. I was under for a month to bring down crime lord, Tony Greico, and everything had been going well until it wasn't. Chip, my CI and I…" Chip, shit! Jay thinks and wonders if he's ok, he does remember the hail of bullets reigning all around them. "Chip! Do you know if he's ok? Was anyone else hurt other than me? We were deep undercover so we weren't in contact with the rest of the unit much."

Hailey looks at him apprehensively, generally not knowing. "I really don't know, but I haven't heard of anyone else from the scene being brought here. I'll find out when I call Voight, which I should probably do soon."

Hailey is about to stand up to go make the call in the hall when a woman walks in, clearly looking like she's from the administrative department.

"Sorry to bother you guys, I'm Gail, I just wanted to come in to verify some of your form info and fill in the blanks if you're up for it?"

Jay nods at her to go ahead. After she asks a bunch of the normal generic questions like his birth date and insurance info she turns to look at Hailey.

"And I assume you're Hailey Upton? You're listed as the emergency contact. May I ask the nature of your relationship, are you related, or married?"

Hailey's eyes go wide as she stammers out, "No… we're not… we're…"

Jay helps out by cutting her off, really wanting this woman gone from his room now. "It's complicated…"

Gail looks between the two of them and senses the awkward tension, not realizing such a question would cause it and clearly embarrassed. "Oh, I see… well, I'm just going to leave that section blank, and you can fill out the rest at your convenience Mr. Halstead. I'm really sorry to have troubled you…" she says before she leaves the form in the holder at the end of bed and exits as quickly as she can.

Jay and Hailey both close their eyes, clearly not ready to drudge up the past, but both getting lost in a memory they can't get out of now….

Hailey's just making the bed after getting out of the shower when she hears Jay call out to her from the kitchen.

"Hey hun, can you bring me my pocket knife when you come out here? I think it's in my bottom drawer."

Hailey smirks to herself, he's always forgetting things. "Yea, sure." She yells back to him.

She makes her way over to his side of the dresser and opens his bottom knickknack drawer, not seeing his knife. She walks back over to their nightstand thinking maybe he left it there before going to bed, but no such luck. Hmm…

"Jay, I'm not seeing it…" she again hollers out.

Not wanting to give up so easily, or have Jay tease her for being blind, she decides to check his sock drawer, knowing he sometimes leaves random stuff in there. She pushes through the garments, feeling out for anything hard, when her hand brushes against a small box. A small ring box. Hailey gasps in shock… she knows she shouldn't open it, but she can't help herself. Tears start to well in her eyes as she stares down at the ring when Jay walks back into their room.

She looks at him, and he looks at her, and for a good while they each just stare at the other in surprise, not knowing what to say. Jay knows he's a goner when Hailey's smile lights up the room and he can't stop himself from grinning too as he walks over to her.

"Jay…?" she says questioningly.

He softly grabs the box from her hand and sighs. "You weren't supposed to see this until next week, I rented us a boat for the day and everything…"

"YES!" she quickly says as she wraps her arms around him.

"Hailey, I didn't even ask you…" he teases her, loving the mild eye roll and nose scrunch he gets out of her.

"Well, ask Halstead, before I get out my gun!" she teases right back.

Jay sighs while chuckling, "This is so not how I wanted this to go, this isn't romantic at all…"

He pleads while she folds her arms looking at him and waiting.

"Alright, alright!.." he says as he gets down on his knee and extends the ring up to her. "Hailey Upton, you're the love of my life, will you do me the honor and be my wife!?"

They both burst into laughter at his corniness, but Hailey juts out her ring finger anyway for him to put it on her.

"Yes… but only if you still rent the boat!" she responds as she winks at him before yanking him back up to kiss him. He gladly responds to her kiss by wrapping her in his arms, lifting her slowly off the ground, and spinning them around.

When they break apart she decides to reiterate again, knowing he won't want his master plan fully ruined and trying to take the blame. "I mean it, I still want that boat ride!"

"Yes ma'am!" he responds as he leans down and kisses her again.

She wraps her arms around his neck again and drags him over to the bed, not caring that it was just made or how they fall on it.

"Hailey, we're gonna be late for work, and you're like, never late…" Jay manages to get out between kisses.

She uses the opportunity to yank his shirt off. "Some rules were meant to be broken…" she murmurs out before she drags his lips to hers again. This is one argument Jay will gladly not win…

Jay opens his eyes first, snapping himself out of the memory, savoring for a second watching Hailey lost in hers. She senses him watching and they both know with a glance at the other that they were caught up in the same recollection.

Jay smiles sadly at her. "It wasn't all bad…" he says, his voice drifting off, lost in the hurt.

She purses her lips at him and nods, sorrow clouding her eyes. "No, no, most of it wasn't… but that was a long time ago… I'm gonna go call Voight…" she says as she practically runs out of the room, as if she's suffocating.

Jay watches on, completely mute, lost for words much like that day so many moons ago outside the Observation Room. Now, like then, all he can get out is, "Yea…" as he watches her exit.

He closes his eyes and wishes for sleep, wanting to forget, knowing neither will come…


[A/N: Wow, thank you all so much for the amazing response to this thus far. The bar seems pretty high so I hope I don't let you down, but I appreciate all the love, truly. There's some more hints & clues filling in the blanks in this chapter, so I hope it helps after the cliffhanger. Sadly, I do have to return to being a productive adult soon & head back to work unfortunately, so I can't promise the recent aggressively steady updates... but I am pretty impressed with the content I've gotten out the past couple weeks, honestly didn't think I'd be able, but here we are- Upstead motivates me ;) ...so until the next update, thank you all again, I hope you enjoy this one!]