The Right Girl.

I do not own Chicago PD or any of the characters.

Upstead one-shot, set during and after 9x01. I wrote this ages ago, after watching 4z21 again and wondering what happened to Jay and Will's mum's engagement ring, so here is my answer. It's a sweet Upstead one-shot. I can't wait to hear your thoughts :)

Jay/Hailey, past Jay/Erin.

"She always said it's not a race, but whoever meets the right girl first, gets the ring."

The engagement ring of the late Catherine Halstead had gone between her two sons over the years; first Jay had it when he thought that he was going to propose to Erin, then Will had given it to his fiancée, Natalie, but she had returned it to him after their engagement ended. Now, the ring sat in a red, velvet box in a safety deposit box. Jay had been surprised when Hailey had proposed to him after Kim had been kidnapped. "I've known for years, I want it to be you and me, always."

This was it. He had given her an answer and now he was down on one knee to ask her same question, "Hailey, will you marry me?" He squeezed her hands in his own, wanting to never let go.

With tears of joy in her eyes Hailey smiled and said, "You don't need to do that, I already did the proposal part."

Jay tilted his head and smiled as he replied, "Well, I'm old-fashioned, okay?" He paused for a couple of seconds; he never thought he would be here, on one knee, asking the woman he loved to spend the rest of her life with him. His marriage with Maggie had been a drunk, non-event. Jay had asked his brother for their mum's ring for propose to Erin, but he hadn't done it. There had been something stopping him and now that Jay was looking up at Hailey, he knew what it. True love. It was Hailey. Jay looked up into Hailey's eyes. His answer had been a simple 'yes' a couple of minutes ago. Of course, Jay knew what her answer was going to be, considering she had asked him first, but he wanted to do it properly. In an old-fashioned way, even if he didn't have a ring to give to Hailey.

Smiling down at him, Hailey bobbed her head as she whispered, in a gentle voice, as if it was the easiest thing she had ever said, "Yes. Yes, I will."

With those simple words, even though Jay had known that they were coming, it was the happiest he had ever felt and he smiled, before he stood up. His lips found Hailey's with a passionate kiss and her arms went around his neck as they continued to kiss. They were engaged. Hailey was going to marry Jay. As Hailey said, it didn't matter that this had been triggered by Kim being shot. They were together now and they loved each other more than anything. With Erin, there had always been something holding Jay back. There was never the case with Hailey. She was the one for him. The right girl, as his mum had always said to her and Will. Only ask a girl to marry if you know she's the right one and, with Hailey, Jay knew. He had known for years.

The next morning Jay was the first to wake and he smiled at Hailey, who was asleep in his arms. Hailey Upton. His partner, his best friend, his fiancée. Jay had said he wanted to propose in an old-fashioned way, but he hadn't given Hailey a ring. He didn't even know if she would want one. This was Hailey, so the best thing was just to ask.

After the couple enjoyed their first morning together as an engaged couple, they drove to the District and, in the car, Hailey could see that Jay was thinking about something, so she asked, quirking her eyebrow, "Are you going to tell me what's on your mind, partner? Fiancée?" Even that word made both of them smile and Jay turned to face her. Hailey could see the love and joy in his eyes. This was so right, for them.

Keeping his hands on the steering wheel Jay shrugged, "I don't know. I'm old-fashioned, but I didn't get you a ring, did I?"

Hailey chuckled softly and replied, "Jay, it wasn't really a planned proposal and I'm not even sure if I'd want a ring, I couldn't really wear it with this job and Jay, I don't need a ring on my finger for this to feel real." Hailey paused, then asked, "Do you want me to wear a ring?"

"Only if you want to, Hailes." Jay paused before he explained, "My mum's engagement ring- she said it wasn't a race, but whoever finds the right girl, gets the ring. And I know you're the one for me, more than anything. I've known for years." Jay looked into Hailey's bright, blue eyes, "So, I could ask Will if you could look at the ring? See if you like it?"

Now Hailey understood and she moved slightly closer to Jay as she told him, "Of course I will. Now, my question is, are you going to wear a wedding ring when we get married?"

Smiling, Jay nodded and told her, "Hailes, of course I will. I'll want everyone to know that I'm yours."

Hailey looked into her eyes before she told her, "Jay, I've been yours for years, way before Kim what happened to Kim, way before we were even together, even. Your proposal was way better than mine."

"No, it wasn't. Yours came from your heart. Besides, if you hadn't, it probably would've taken me years to ask you. Shall we go in, fiancé?"

Chuckling Hailey nodded and replied, "Yes, let's do that, fiancée." If they hadn't been in the car park at work, their lips would have met and they would have held each other, but just their eyes met. Blue met green.

It felt strange to be in the bullpen, as if nothing had changed, but in a couple of days, so much had changed. So much had changed, for better and worse. The better was that Jay and Hailey were engaged, they were going to be married and spent the rest of their lives together.

After their shift Hailey went to see Kim. She knew that she should tell Jay the truth, about Roy. They were going to be married, it was only right that she tell him that. He needed to know the truth. She knew that what had happened had made her propose to Jay, as well as Kim, not wanting to lose him, ever. Not a word of what she had said to Jay had been a lie, but it wasn't the total truth. Jay was going to be her husband, didn't he deserve all of the truth, from the woman who was going to become his wife? Hailey was still surprised with herself that she had proposed to Jay, but it was still the best thing in her life and, in that moment after all that had happened with Voight and Roy, all she had wanted was to be with Jay, forever. She did want to marry him. She wanted to be Jay Halstead's wife and spent the rest of her life with him.

Jay found Will in the doctors' lounge, and he suddenly found himself feeling nervous. Talking about this with Will was something he had never envisioned himself doing, until Hailey. Will looked up and asked, "Hey, man, what's up?"

Pressing his lips together, Jay put his hands on his hips as a huge smile spread across his face before he replied, "I can't believe I'm actually here, asking this, but can I have Mum's ring?" When his brother raised his eyebrows, he added, in a tone he only used to talk about Hailey, "I've found the right girl, Will."

That was all that Will needed to give his brother a hug. "You're going to propose to Hailey? When is this happening? Does she know?"

With a smile, Jay tilted his head and replied, with a light chuckle, "It's a long story, but I already proposed to her. Last night, but she proposed to me before that. I said I was old-fashioned. I got down on one knee, but I didn't have a ring and I want to see if she likes it." He paused and cocked his head, "Why are you looking at me like that?"

Will smiled sadly and repeated their mum's words, "It's not a race, but whoever meets the right girl first gets the ring. Jay, I was surprised when you wanted the ring to Erin, years ago. I knew it was a mistake and, deep down, you did too. I know there's no mistake with Hailey. She's your partner, you've loved her for years and you've finally realised it. Hailey's the right girl for you, brother, I know Mum would love Hailey to have her ring. It's never really belonged to anyone else, has it? Not Natalie. I think the ring has been Hailey's for years, you guys just didn't know it."

Chuckling softly, Jay joked, "Wow, you put a lot of thought into my love life."

"Jay, if it weren't for Hailey, I think I would've lost you." There was a dead silence between the two brothers for a couple of seconds, before Will handed Jay the key. "Get the ring and show it to Hailey. You've waited long enough."

"Thanks, man. Love you."

Smiling fondly, Will replied, "You, too, little brother." Jay nodded and walked away, leaving Will watching him as he walked away, thinking about all that his brother had been through and all that he had overcome to be here, ready to marry the woman he loved.

Knowing that Jay was going to come home with his mum's ring and propose to her 'properly' as he put it (the thought made Hailey smile, they had already had two proposals, one from each of them), she found a blue dress and let her blonde curls fall naturally and she laid out a nice outfit for Jay. She heard the door of the apartment open and her eyes went to Jay and then they landed on the velvet, red box, where his mum's ring was.

"What's all this?" Jay asked, her fiancée.

"I thought I'd dress up- make it feel like a planned proposal, for the third time. They do say the third time's a charm." Hailey quirked her eyebrows before she kissed Jay gently and told him, "Your clothes are on the bed."

Resting his head against hers, Jay murmured, "Hailes, there's no pressure to like this ring. You don't even need to wear an engagement ring if you don't want to. I'm marrying you, that's all that matters."

Smiling, Hailey bobbed her head, "I know, but I wanted this moment to feel special. You said yourself: You're old-fashioned, Jay Halstead."

As much as he didn't want to leave Hailey's side Jay went to the bedroom to change and Hailey's eyes fell onto the red, velvet box and she knew that she couldn't help herself, so she walked over to it and opened it, very slowly. The ring was a blue diamond and it was beautiful and, in that second, Hailey knew that she wanted to wear that ring for the rest of her life, right next to the wedding ring she would wear once she and Jay were married.

As he was changing Jay was thinking about Will's words earlier and he knew that his brother was right, about how he had loved Hailey for years, she was his partner, and the ring had been Hailey's long before they had realised their feelings for each other.

Jay left the bedroom to re-join Hailey and he took in all of her. She was so beautiful. Hailey walked over to him and wrapped her arms around him and his hands found her waist, before she asked, "Now, Jay Halstead, is there something you'd like to ask me?"

With a smile on his own face, Jay replied, "Yes, there is, Hailey Anne Upton, and allow me to go down on one knee, in an old-fashioned way." Hailey chuckled softly and her blue eyes were already shining with tears. Slowly and looking into Hailey's eyes, Jay went down onto one knee and took both of his hands in his own. It was only then that his eyes fell on the ring on his finger. His mum's ring. The ring which had been Hailey's, in his heart, for years. Swallowing against the lump in his throat, Jay whispered, "You're already wearing it. Will did say it's been yours for years."

Watching how Jay's fingers fiddled against the ring, Hailey whispered, "It's a perfect fit." Like Jay had done, slowly, Hailey went down to one knee, still holding Jay's hand, so that they were eye level. Bright, blue eyes met green ones, so she whispered, "Now, it's perfect, because we're both down on one knee, together."

Jay smiled and all of his love for Hailey was in that single kiss that he gave her, before he asked, breathlessly, "Hailey, my mum always said to me and Will, it isn't a race, but whoever gets the girl, gets the ring and you've been the one for me, for longer than I realised, so will you marry me?"

"Of course I will, Jay Halstead." Hailey replied, with the biggest smile on her face. She looked down at the ring and told him, "I've known that you were the right one for me, for years too, so it makes this ring even more special. This is us, our new chapter and I love you more than anything in this world."

Jay squeezed her hands and nodded, "Yeah, and we'll be together, forever." He chuckled and tilted his head, "This wasn't the third proposal I was planning on. I was going to bend down on one knee, then give you the ring-"

Hailey silenced Jay with a gentle kiss, still holding his hands as she whispered, "But it's perfect, Jay, it will always be perfect, with you."

….

The past couple of months had been hard for Jay and Hailey and it was not how they had thought their first months as an engaged couple would go. All that had fitted with their plan was moving in together. Hailey thought that, when Jay found out about Roy, he might leave, that she would give the engagement ring back, but he didn't. Jay didn't leave. Hailey could see how much pressure Jay was under; he was trying to save her from the FBI. She felt like a passenger in her own life, she was just waiting and hoping that it would all be alright. She knew that she and Jay could never have a life together if she went to prison.

After her shift, Hailey knew that Jay was with Agent North, but she went home and changed into leggings and a jumper. Home. Where she and Jay lived, where they were supposed to be starting their new lives together, one that wasn't started under the shadow of Voight and Roy.

Hailey almost jumped as she heard the door open. It was Jay and she moved on the sofa, reading his face. She sat bolt upright on the sofa, the tension clear in her body. For Jay, these past couple of months had been awful, but it was finally over. He knew that there was a part of him that would never be the same, but he had done it all to save Hailey. The love of his life. His fiancée. Even thought their relationship hadn't been in a good place, Hailey had never taken off her engagement ring and Jay hadn't wanted her to. You truly love Hailey Upton, don't you? Those had been North's words and Jay knew that nothing truer had ever been spoken.

"Hey." In that moment, it sounded slightly pathetic leaving Hailey's mouth, but, in that moment, she couldn't think of anything else to say. Her voice, her eyes, her whole body, felt so heavy and tired. It seemed like a different world since they had proposed to each other. A different life and Hailey wanted Jay back, she wanted her fiancée back. Her Jay Halstead.

Jay closed the door and placed his keys and wallet on the table and walked over to Hailey and Hailey could feel herself holding a breath, as she continued to sit up straight on the sofa. Jay looked at her and all he said was, "It worked." Without another word, he sat down on the sofa and Hailey felt herself settling on the sofa. Her eyes landed on her engagement ring, the promise which had been made between them.

With a small smile, in a very tired voice, Hailey looked into Jay's green eyes and told him, "I love you."

Without a second of hesitation, Jay looked into her eyes and told her, "I love you, too." Like hers, his voice was tired, but it also full of something else. Hailey wasn't sure if it was love or hope, but she wanted, they needed it to be either or both of those. In a swift motion, Jay moved closer to her on the sofa and placed a hand against her cheek, moving away her long, blonde hair. His green eyes went up and down Hailey's whole face, before he simply said, with his voice breaking with emotion, "Marry me. Now."

Hailey's answer was just to look into his eyes, because her answer was already in her own eyes. She smiled, then suggested, "Maybe tomorrow afternoon? We have the time off and we need to find the right rings."

"That's perfect, Hailes."

The next morning, they both chose their best clothes and applied for a licence to get married, before they went to the courthouse, they needed to find rings. Their wedding rings. It wasn't until Hailey had proposed that Jay had ever seen a ring on his finger and he wanted one of hers, right next to her engagement ring, the ring that had always been hers, the right girl.

After a long time of searching, Jay and Hailey found identical black, rubber wedding rings. They couldn't have metal ones because of their jobs, but these were perfect and Hailey wanted to see what her wedding ring looked like next to her engagement ring.

At the courthouse, it seemed like a blur. As they exchanged wedding rings, along with their vows, Jay and Hailey smiled at each other. These rings were their vows to each other, their promise of their life together. Hailey put Jay's ring on first and, as she did, she saw the loving smile on his face and in his eyes. As Jay slipped the ring onto her finger, Hailey smiled as it lay next to her engagement ring. They looked perfect together. As Jay signed the paper, Hailey's eyes went to his finger, where his wedding ring was now lying. It felt like a dream, one she wanted to live for the rest of her life. At the end of the ceremony, Hailey took hold of Jay's hands and she pressed her wedding ring against his hand and their marriage was sealed with their first kiss as a married couple. Their wedding rings. Jay and Hailey were married. Married. Hailey knew that she was going to change her name to Halstead, but keep Upton at work.

When Jay and Hailey returned home, they stood together, admiring their wedding rings. They looked so perfect. This was the start of their new lives together. Hailey took off her engagement ring to put it somewhere safe and when Jay raised his eyebrows, she just simply said, "Now, we match."

With a smile on her lips Jay took hold of Hailey's hand and ran his finger against her wedding ring before he murmured, "Yes, we do, Hailey Halstead." The blue diamond in the engagement ring glowed in the dark and it was still so important, but their wedding rings were a symbol of their marriage and, as Jay and Hailey enjoyed their first night together as a married couple, their eyes kept landing on each other's wedding rings. They were together forever. Jay's mum would've been proud: Jay had given her ring to the right girl (it had been hers for years in their hearts anyway) and now (after three proposals and months of hardships) Hailey was his wife. Their lives were joined forever, symbolised by the black wedding rings on their fingers, rings which they would wear for the rest of their lives.