A collection of Upstead one-shots following their growing relationship through a year of holidays

Jay and Hailey's daughter is old enough to start understanding more Christmas traditions, so Vanessa convinces Hailey to buy her an Elf on the Shelf. They expected the elf to bring their daughter a lot of joy, but they didn't expect her to bring them the best gift of all. Upstead Oneshot.

Christmas shouldn't be about avoiding your mother, but when Hailey tries to do just that, Jay gives her the strength to do the opposite. What neither of them was necessarily expecting, though, was that he'd get the strength to do something he'd been wanting to do for a while as well. Upstead S7 oneshot.

Jay and Hailey want the perfect apartment to move into together, but the perfect apartment isn't a balcony or large kitchen; rather, the perfect apartment is one they can grow together and love each other endlessly in. Upstead oneshot.

Hailey and Jay grew up debating if they'd have kids when they're older, but it's not until they're dating each other that the debate stops and becomes a real conversation between two people. Upstead.

He knows he's going to love this woman for the rest of his life, and he can't imagine whatever it could be that she's keeping from him, but he also knows that nothing will never make him not want this with her.

Hailey freed herself from her father when she was 20, but it isn't until ten years later with Jay that she feels like she's really ready for a better future. Upstead friendship and dating oneshot. Or Hailey has a secret tattoo and the only one she tells its story to is Jay.

She knows she should feel relief because at least now the truth is out there, but she doesn't. She just feels the guilt and the shame tightening their hold on her, a crushing ache rushing through her because she knows what comes next. She's going to lose him.

What if Tim and Lucy met Jay and Hailey purely by accident? My take on how that meeting would go, and how it would lead to an Upstead/Chenford double date that all the fans want! :) Just a fun little one-shot until CPD & The Rookie come back! Mentions of other characters, but mainly these two ships. This is my first fic in like almost 6 months, but regardless, hope y'all enjoy it!

It was another undercover mission, only this time they were expected to play bride and groom. A plan is made, the stage is set and the vows ready, all in the hopes of catching an elusive target. But as always, with these things, they rarely go to plan. [Upstead Fake wedding - Oneshot]

Jay and Hailey go for a walk every Sunday morning, and almost every time that it rains while they're on the walk, Jay makes sure to kiss Hailey because it's his favorite "couple thing" to do. Upstead Dating/Married Oneshot. Upstead Week!

After Hailey's holster breaks, Jay lets her borrow his thigh holster. But, he immediately regrets it when it gets a little hard to focus throughout the day / or a short little one-shot for Day 7 of Upstead Appreciation based on the prompt: "You're an idiot." "But you love me."

"You're not supposed to call your boyfriend dude." / or a little drabble for day 4 of upstead appreciation week based on the prompt "kiss me"

Jay thought he had every inch of Hailey memorized, but when he finds a scar that he's not familiar with, he reminds her that he loves all of her - past and all. Dating Upstead Oneshot. Upstead Week!

And maybe a game of truth or dare is a little silly, especially for two elite detectives. But she's bored and he's her best friend. So, if she can make him laugh and learn something new about him, she thinks it will be a night well spent. / or a little oneshot for Day 2 of Upstead Appreciation Week based on the prompt "It's you, it always has been."

"I'm sorry, but is that my shirt?" / A little drabble written for Day 1 of Upstead Appreciation Week

When an injury at work leaves Hailey with retrograde amnesia, she has no recollection of Jay or their relationship. It's up to Jay to remind her who he is and help her fall in love with him all over again.

Jay's past is his past and most days he'd rather it stayed that way, but occasionally he needs a reminder of how much he's survived, so he steps back into that part of his life. Hailey confirms that she's going to be there for him each step of the way no matter how hard of a pill it is to swallow. Post 7x10 Upstead friendship oneshot.

hey spend every day together, small talk in the truck or glancing at each other from across their joined desks, but she is still looking forward to this: to slow kisses with nowhere to be and not having to hide that she loves him more than she can explain / or a post 8x11 day off fic

They're each other's constant and anchor when everything seems to be going wrong and it's their unspoken moments that make them truly who they are together. Three missing Upstead moments from the S8 finale.

She doesn't care how the words sound needy or insecure because they both know that's not what it is. She just wants him, wants him always.

AKA: The five times Jay Halstead buys Hailey Upton flowers and the one time he doesn't

The water is out at your apartment so I invited you to stay at mine but my couch is crappy so now we are sharing a bed and by the way I think I love you/ Upstead forced bedsharing fic

pillow talk: the intimate, authentic, unguarded conversation that occurs between two lovers

"I just want you." She swears her heart drops to her stomach. It's just four words, but the way he says them with such tenderness and pure desire and the way he looks at her as he says them makes everything inside of her ache down to the bone.

Kim needs to decide who is the best option for Makayla if something were to happen to herself and she was no longer able to care for her. Her gut is telling her one person, but that same person hasn't been talking to her lately, so maybe there's a better option for her little family. Oneshot based off of the 8x13 promo.

Two people, struggling in their own way...Fate consistently bringing them together. Do they fight it? Would it matter if they tried? UPSTEAD ALTERNATE ENDING ADDED

While he is working undercover, Jay meets a stranger in a club with bright blue eyes and now, she is all he can think of. Only problem is, he doesn't know her name. / First Meet AU

After just a year of dating and a short engagement, Jay and Hailey need to navigate their first year of being a married couple. Upstead future.

Kim needs Hailey to watch Makayla while she goes to see Adam after his dad's retirement party which gives Hailey time to reflect on her relationship with Jay while the little girl sleeps. Upstead. Mentions of Burzek. Based on 8x10. Oneshot.

She knows he means staying more than just tonight and there's a moment, maybe for the first time in her life, where the future doesn't worry her or scare her. Not when it includes him, them.

Just some flirty missing scenes from 8x09 after Cooper punches Jay. Flirty Upstead One-shot

friend. confidant. lover. they were all of it. they were everything.

Jay and Hailey have their thing: They talk about the case, they drink a couple of beers and they watch some Netflix. But as the episodes of the show progress, so does their relationship. (Two-shot of following the evolution of Jay and Hailey's relationship from partners to friends to more.)

The three times Hailey is jealous of Jay with another girl

Hailey comes home after Jay's been in the hospital and wants to be alone, but Vanessa knows that's the opposite of what she really needs right then. Post 7x10. Upjas.

Missing scene from 8x06: A snippet of what happened between Jay and Hailey during those 6 hours in the truck

It still feels like a dream to her that she can be like this with him. Kissing him, touching him, loving him.

Nathan Scott has to work on Valentine's Day, but his secretary surprises him with a special gift.

It's a strange thing how fast one's world can completely change (Written for Day 7 of the Upstead Valentine's Love Song Challenge)

A bucket list: a number of experiences or achievements that a person hopes to have or accomplish during their lifetime (Or where Hailey asks Jay what is on his bucket list, but the only thing he still wants is a life with her)

The last thing she remembered before falling asleep is him pulling her even tighter against him, his head moving so his nose pressed against her collarbone. She could hear him mumbling and she wasn't sure if he knew the words coming out of his mouth, but she just held him tighter, finally letting the tears for him fall from her eyes - Inspired by 8x06

After Hailey goes out with another guy, Jay finds himself drinking away his pain at Molly's. After a heart to heart with Will, Jay comes to the realization that he and Hailey do a lot of things that friends don't. (Fluffy Jealousy Fic for Day 5 of the Upstead Love Song Challenge)

After two years of dating, Jay takes Hailey back to the same bar where it all began with one plan in mind: asking her to marry him. Written for Day Two of the Upstead Valentine's Love Song Challenge

After Jay's truck gets totaled in an accident, Jay and Hailey go car shopping for a replacement, but not without hitting a bump in the road

Jay is Hailey's reason to stay, and now all she needs is for him to stay in her apartment...in her bed...in her arms. 8x03-8x04 Upstead.

Missing scene from 8x05: Jay and Hailey talk about Kim fostering Mikayla and their own thoughts about children in the future.

What happened between 8x03 and 8x04, at least in my mind. Jay and Hailey leave the bar and head back to her place. Rated M.

Three years of anticipation and curiosity and pushing down feelings she thought she shouldn't have ever had has led her to this moment.

Hailey discussed the FBI job offer with Jay and told him she wasn't going to take it. Find out what happens next. Post 8x03, this is what I would've liked, and would still like to see happen.

AKA: the five times Jay asks Hailey to dance and the one time that he doesn't

Inspired by 8x03 and what I hope happens after! Truckstead! WARNING: If you somehow haven't watched 8x03, this has spoilers for that episode. Otherwise, enjoy!

When Jay is absent unexpectedly from work one morning, the team becomes worried. Hailey and Kim head out to track him down, and Kim discovers a few interesting details about her co-workers along the way. Upstead!

Jay hates when he and Hailey have to take off their wedding rings for work, so he makes an unexpected suggestion: matching wedding band tattoos.

Jay finds himself unable to ignore his friends and helps them pick up the pieces of the fallout of Kim's miscarriage. Oneshot. Mostly Jay/Kim friendship, but a little Upstead too and Adam. Based around 7x13-14.

Hailey Upton and Adam Ruzek have been friends for as long as they can remember. When Hailey leaves her prestigious private school to be with Adam in her junior year, she's introduced to a new group of people who feel strangely like home.

When Jay and Hailey are stood up by their friends at the annual winter festival, they decided to enjoy themselves with some ice skating and winter festivities. Heavy flirting and fluff ensues. Upstead oneshot

written for chicago pd secret santa 2020 - hailey needs a date to her childhood friend's wedding and jay is more than happy to help out. after getting mistaken for a couple numerous times, they decide to have some fun with it... until the line between pretend and reality becomes blurred.

All things Upstead throughout Season 7, both what actually happened in the show and what I wish happened! Enjoy

Kim and Adam are getting married and when Erin decides to go, she must face the music of the mess she had left behind in Chicago years before. Future fic. Upstead oneshot, but mentions of Linstead.

Here's a quickie of a quickie...inspired by the scene in 5x10 of Jay and Camilia. Rated M. Enjoy!

I'm sorry for the way I hurt you, making you walk away. I should have taken the time to tell you...but if I told you I loved you, would it make you want to stay? / aka: what happens when Hailey's offered the FBI job and Jay is forced to confront his feelings. An Upstead one-shot based off the 8x03 promo!

What happens when Hailey stops by Jay's apartment after a girl's night out? Smut ensues.

Hailey confesses to Jay the night before being sent to NY to work with the FBI. And while all she desires is happiness with her partner, the love of her life, someone from her past threatens to blow it all to pieces.

Without another word, she walked away, passing by him so closely he had to step back. Voight looked at him, the look on his face surprising as there was a hint of what Jay thought was amusement there. All he could do was bite his tongue, pretend to act surprised when he really wasn't.

It felt like déjà vu, a completely valid feeling because she had been here before, over a year ago. The similarities were glaring: her partner going off on a mission to ease his guilt and satisfy his need to protect and save everyone, all while going rogue and getting shot, leaving her to find him. - Post 7x09 AU

This is a short fluffy prompt request. Jay's been away for an undercover operation with narcotics for God knows how long and Hailey's missing her partner and fiancé. This is my take on their reunion moment.

I posted a prompt list over on Tumblr and these are the little drabbles I wrote from the requests I received. Just a few little blurbs of Upstead kisses. Enjoy!

written based on prompt: "running is supposed to be good for your health except i seem to have sprained my ankle and i took you out with me i'm so sorry." - runner hailey/innocent bystander jay au

Jay and Hailey go to a haunted house...

A series of pregnancy one-shots that follow Hailey and Jay's journey as first time expectant parents. A variety of Upstead stories with Intelligence Unit and One Chicago family bonding :) Open for requests through reviews/ DMs.

AU where Hailey Upton isn't a cop and meets Jay Halstead under different circumstances. This story follows the development of their relationship in a world where they don't have to overcome the obstacle of working together.

Upstead in a cabin in the woods. Happy Wednesday!

With the help of Vanessa and Will, Hailey and Jay relive the last three years of their partnership and come to the same life-altering conclusion.

Smut. Pure Smut. But also, Upstead's first time. Rated M!

written based on prompt: "we hate each other but we both have a mutual friend so we have to put up with each other" - burzek wedding jay & hailey as best man & maid of honour au

written based on prompt: "our kids are bitter rivals and the only time we ever meet is when we're both called to the principal's office and whatever maybe i think you're kind of cute but your kid's a monster" - lawyer hailey/detective jay au single parents

written based on the prompt: "my friend dragged me to this party and i just saw my ex - quick, make out with me" - university au

"i'm assuming she has a concussion, or else she's just naturally a pain in the ass of people who actively save her life." - "excuse me? you also actively put my life in danger!" - upstead au - prompt: hailey is walking home from her bakery late at night, when she is caught in the crossfire of the cpd. in det. jay's attempt to save her life, he ends up injuring her anyway.

"who are you calling a groupie? now shut the hell up before i go over there and shove my foot up your ass!" - prompt: jay and hailey go to rival high schools, but come together at a party after their latest 'friendly' match. jay starts off on the wrong foot but redeems himself by the end of the night by inadvertently becoming hailey's knight in shining armour. (high school au)

Kim invites everyone from Intelligence out for a night at the club and Hailey and Jay take the opportunity to have proper fun for the first time in months spending the entire night glued to each other's sides ignoring everyone's comments that they need to finally bit the bullet and start dating. Upstead flirty friendship. Oneshot?

Just another smut shot...

Based on the request for angry/make up sex. Enjoy!

Hailey is forced to deal with something very unexpected. How will Jay handle the situation? Will it pull them closer together or destroy their new relationship? Stay tuned to find out! Set S8- ish. Rated T for later chapters, the first few probably won't be.

"i'm sorry; are we here to distract me or sit around and talk about our feelings?" - prompt: hailey is going on a date and jay is in severe need of a distraction. he calls on his intelligence boys for a guy's night, but that's all forgotten when hailey shows up after her date.

Hailey gets drunk while out with 51 and Jay gets jealous so decides the best thing to do is remove her from the situation meaning he has to take care of Drunk Hailey in his apartment. Post season seven. Upstead friendship. Alcohol is definitely involved in all parts of the story.

Based on the prompt's: Really? You wanna have sex…. here? Now?" and "I may or may not have left some…. marks."

"Apparently all our friends have a bet going that we end up together.

They both knew they couldn't just be friends anymore, and when the music changes it provides the perfect romantic setting for them to take that next step. (upstead one-shot)

The aftermath of 7x09 and what the future holds for Hailey and Jay together. Rated M for future chapters, however the starting chapters aren't Rated M.

This is probably going to turn into a collection of one shots, not necessarily in any particular order or with any real plot lines. Just some smutty goodness from our favorite duo. Again this 'story' is NSFW so if you're not into that sort of thing, this one probably isn't for you. 18 .

literally no summary because i CAN'T find the plot. it's *chef's kiss* upstead smut.

Jay unexpectedly runs into a boy from his past, but can't quite place who he was until late at night. It's not until their second encounter that Jay realizes how much he had impacted the boy four years before. Upstead friendship. Oneshot. Reaction to 3x07 set at Beginning of season 7.

A calm Saturday with no cases to have to worry about is a rare occurrence for members of the CPD Intelligence Unit, so Jay and Hailey had planned to make the most of it by spending some much deserved family time with their 10 mo daughter. What happens to their plans when the doorbell rings to reveal an unexpected visitor? Some Upstead domestic bliss w/ a Mousey suprise!

all she wants is a cup of hot coffee to get her through this next phase of studying; instead, her cell phone ends up cracked, her textbook lands on the floor with a thud, her cup of steaming hot coffee seeps through her cable knit sweater and she's crying in the middle of a university coffeeshop.

It's New Year's Eve and Jay hates Hailey's boyfriend. *Upstead College AU (Booth vs. Hailey)

Kim's tired and just over her own life problems, so she decides to put herself into Jay and Hailey's. She's sick of them beating around the bush and wants them to be honest about their feelings for each other. Takes place in 7x16 "Intimate Violence." Upstead friendship. Oneshot.

When Hailey gets food poisoning and Jay takes care of her all day, it's only fair that she do the same when he gets sick a month later, right? Upstead friendship with Vanessa pushing Hailey toward acknowledging that she might actually have feelings for her partner. Oneshot.

Future Upstead oneshot. Three times Hailey realized Jay was the perfect partner for her during the final weeks of her pregnancy and one time Jay realized she was his.

Hindsight is 20/20...That's what they say. Join Hailey and her daughter on a path to freedom. A year of healing and rebuilding. AU with original characters.

Hailey has one heck of a proposition for Jay, something that may change everything, but might be just what they need. Afterall, partners and friends help each other with everything, right?

Previously known as 'First Date'. Brooke Davis makes the move to Chicago, here she runs into the handsome Detective Jay Halstead.

Hailey and Jay are only engaged for 13 days and yet they still manage to pull off a wedding neither of them could ever forget. Upstead one-shot. Lots of Intelligence and Will throughout. Can be read alone or as a prequel for my story We Can.

Jay and Hailey's relationship grows on what happens to be some of the worst and best days of Adam and Kim's lives as they wonder what they'd do in Burzek's situation. Set after 7x11 and 7x13. Upstead friendship that perhaps blossoms into something more.

Hailey never noticed how many women Jay was friends with until one day at a softball tournament. No angst, just fun! My inspiration for this was Jay season 1&2 when he had a bit of a reputation for being a play boy. It is so different from the mature Jay that Hailey has always known and I wanted to play with that a little.

Set at the end of "Ghosts" (5x18). Jay can't bring it in himself to leave Hailey despite everything she says. Upstead friendship. One-shot.

A collection of mini fics and drabbles looking in the lives of Jay Halstead and Hailey Upton.

"alright, so answer me this. hypothetically, if hailey was to go home with, oh, i don't know, severide or something, would you be completely okay with that?" - prompt: the whole gang is at molly's having a great time until will halstead corners jay about his relationship with hailey and advises him to take his girl home.

It was supposed to be just a simple movie night between partners... wasn't it? This is what happens when Upstead lets their tension boil over!

The sigh that escaped him was one of relief, one he didn't know he was holding inside. In the back of his mind, he worried that her threat from earlier would come true, that whatever just happened would happen and she would walk into the district tomorrow and demand a new partner. - Season 6 AU

"get your ass back in this bed because you are not sleeping on the couch." - prompt: during one of chicago's coldest winter nights, the power and heat in hailey's building is out. jay humbly offers his apartment - until his power goes out as well.

"if i were to go down like this, stuck in this elevator, i wouldn't mind if the last thing i saw was your face." - prompt: hailey and jay are taking an elevator ride when chicago is hit with an earthquake.

Detectives Hailey Upton and Jay Halstead's working relationship has turned into a great friendship, but what happens when the lines between being just friends and being something more get blurred? Upstead fan-fic.

This fic is post 7x10 with some more context and an ending that we all wanted! WARNING: You will endure the Upstead feels! Also, listen to the song Look After You by The Fray before, during or after reading this for maximum feels!

Jay takes advantage of the fact that Hailey is distracted on the phone. Upstead smut.

Jay Halstead and OC. They have a past & maybe a present if they can get past all the hurt. Jay will discover she is his old & new flame; maybe his forever flame. Predominately CPD and Halstead but crosses over with CFD and Severide, Shay, MED and Will & Natalie A LOT!

Jay loses someone close to him and it breaks him. Not linstead. Sorry not sorry

Who doesn't want to get paid to take a dream vacation? Erin and Jay are going undercover as newlyweds on a luxary liner to catch a thief. How long before business and pleasure collide?