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a love bigger than the ocean

Summary:

From the minute he first mentioned Hailey, his mom had a good feeling about her. She has always been his number one supporter when it came to his relationship with Hailey, almost like some part of her knew that this girl would be something important in her son’s life.

or...

9 major moments from Jay and Hailey’s relationship in a world where Mama Halstead is still alive

Notes:

Hello friends! I'm excited to share a new mini series. This is a fic I've been working on for a few weeks that was supposed to be a one shot and not so surprisingly got too long so here we are. It's 9 major moments of Upstead's relationship but Jay's mom is still alive and very involved! I am so excited to share all this family fluff with you. I won't be doing weekly updates for this fic like I do for oms but the fic is completed so I'm hoping to update somewhat regularly. Hope you all enjoy!

Title is from "Mother" by sleeping at last

Chapter Text

(June 2017)

Jay has dinner with his mom at least once a month.

For the good months, he tries to do it more. But it's hard with his job and lining up their schedules, and thankfully, his mom is understanding of that. On the months when he manages to see her four or five times, she's thrilled. During the months he only sees her once, she's equally happy.

It's normally dinner with just them, sometimes with Will, and rarely with their father. They save that for real family dinners, like holidays and birthdays, not the little tradition Jay has been doing with his mom since he came back to Chicago from Afghanistan.

"So, what's new?"

It's the question his mom always starts with after they've ordered their drinks at whatever diner or restaurant they find themselves at. It seems to be her catch-all question - see if there is anything he wants to talk about in regards to work or family or friends or dating - and then they see where the conversation takes them.

"Not much," Jay hums, his voice fading into the soft buzz of the diner. They come here often, and it's never crowded, but still always homey. He likes it. "Got a new partner at work. That girl from robbery homicide I was telling you about before."

The last time he saw his mom, he mentioned the new, temporary addition to his team - Upton. Most of their conversation was focused on Jay's relationship, though, and the fact that Erin had just left for New York. He barely even mentioned Upton, just told his mom that there was someone new and she might be with them for a bit.

It was clear for years that his mom liked Erin but didn't love her, that she put a smile on her face every time she was around her for the sake of her boy. It was at their last dinner that his mom told him that while it hurt now, it might be for the best - better things were coming for him. She knew it.

"The Hailey girl, right? The one from the bank robbery?"

Jay bobs his head. "Upton, yeah."

"And how's that been?"

Jay sucks in a low breath as he thinks about his answer - he can lie to his coworkers and even his boss but there is no way he can lie to his mother. She'll see right through him.

"Different. I don't think we're gonna work well together."

"And why's that?"

"We're…" he pauses as he tries to think of the right word for everything that's currently wrong. "...different. And we're both too stubborn."

His mom chuckles at the last part, knowing the depth of his stubbornness well as the one who has raised him.

"What's wrong with different?"

The tone of his mom's voice lets him know that she's not curious - she's trying to make a point in a gentle way. Jay thinks that things won't work out with this new partner because she's not what he's used to. She's not Erin.

"She does things differently," Jay continues. "And she's way too perky."

Upton is the calmest, most composed person he knows while they are on the clock. But when he sees her in the locker room in the morning, she's all smiles, and on the two occasions the team has dragged them all out to Mollys since she started, he's come to learn that her laugh is loud and infectious.

"Maybe that's just what you need," his mother says, straight as an arrow, and it feels like she is going to say something more, but the waiter comes back over with their drinks. She flashes the young man a smile as he places their drinks down on the table - water for Jay and sweet tea for her - not directing her attention back towards her son until the waiter is out of earshot.

"You always seem so serious when you talk about work. Maybe this girl will help you loosen up -"

"Mom -"

"I'm just saying, hon," his mom cuts off his groaning in the same way she has since he was little. Her voice is soft, genuine, and it gets Jay to focus on what she's saying, despite his not wanting to hear it. "Give the girl a chance. Does she seem like a good cop?"

As much as Hailey being on the team irks him some days, he can't deny that she's a good cop. A great one even. From the minute that he met her at the bank robbery, he was taken aback by her police skills. To later find out that she was meritoriously promoted was a surprise, but not a shock. She's good at her job, and she knows it. Takes pride in it.

They've only been partners a few days but Jay has seen it too. She's precise in her decisions. Careful with her movements. Thorough with the details of the case. Yet, when they are with victims, she is kind and understanding, empathetic in a way that he has never experienced before.

She's a great cop. Probably a better one than him.

Jay bobs his head. "She's good." He gives his mother the simple, straightforward answer, still holding onto the last bit of stubbornness that he is sure she can see right through.

Still, his mother hums contently. "Well then, at the very least, you'll be safe out there. Besides, maybe she's not as bad as you think."

Jay gives a wordless nod as he processes what his mom has said. His mom has always been a good judge of character and if he's honest, there's really nothing wrong with Upton. He's just pissed about the situation that he's in and he's taking it out on her. Voight could have paired him up with anyone and he still would have been angry because it's not who his partner is supposed to be.

But that partner is gone. And now his partner is Upton. And he's got to make it work. At the very least, he has to try so that when he sees his mom next, he won't get another talking to about how he needs to give his partner a chance.

Besides - maybe his mom is right and Upton is not all that bad. She's always been wise, his mom.

"I'll try to give her a fair shot," Jay finally concedes. "Now tell me all that's going on in Canaryville."