jay halstead loves hailey upton pass it on
seen from Macao SAR China
seen from China
seen from United States

seen from United States
seen from Italy
seen from China

seen from China
seen from Russia
seen from Poland
seen from China

seen from France
seen from Canada

seen from United Kingdom
seen from Germany

seen from United States
seen from United States

seen from Italy

seen from Italy

seen from Italy
seen from United Kingdom
jay halstead loves hailey upton pass it on
Love Drunk
Happy almost Valentine’s Day! Here’s a long, annoyingly fluffy Upstead one-shot inspired by the song Afterglow by Ed Sheeran. Written for the “Upstead Valentine's Love Songs Challenge” on @upsteadofficial. Enjoy!
fic: the goosebumps start to raise (an Upstead one-shot)
For the first day of the Upstead Christmas prompt challenge -- SNOW.
Rated T | 1005 words | Title from Sweater Weather by The Neighbourhood
For the first time in a long time, Jay wakes up on his own -- before his alarm, without his phone ringing, without Hailey's lips pressing against his skin, drawing him eagerly from sleep.
He's cold, even though her body is pressed against his chest, and it takes him a moment to realize why.
The curtains are pulled back just slightly, and he can see snow falling outside the window, heavy enough he knows it'll still coat the ground when they finally have to get up.
Upstead Valentine's Love Song Challenge ❤️
9th Feb 2021
It was a regular day in Chicago, the team always in pursuit of drug runners and dangerous gangbangers. Everything was the same, except for a certain blonde detective and her partner. They were no longer just partners...
Boyfriend and Girlfriend they were.
It's been a months since their relationship evolved and things could not be going smoother. Sure, there were some bumps here and there, with Hailey's dad and Jay going undercover, but things between then were just effortless and easy.
Upon walking through the door, the pair crashed on the couch, exhausted from their day. Two suspects decided to bolt when they approached them, leading Halstead and Upton on a cardio workout. They only managed to catch the offenders thanks to patrol who rolled just in the nick of time.
As Hailey looked over at Jay, she saw him in a state she didn't really see him in. Ever. His eyes were closed, not a wrinkle on his forehead. He was relaxed. Hailey smiled at the thought, "how did I get so lucky?" and intertwined her petite hand with his. Fingers still interlocked, Jay swung his arm around his girl, pulling her close to him.
Deciding that they needed food, Hailey placed a kiss on Jay's temple and got up to order some Bartoli's for dinner. A very late dinner considering it was already past midnight, grateful that the pizza place closed at 2am. Jay got up and hugged her from behind as she poured herself some tea. The blonde leaned back into him as he wrapped his arms around her in a warm embrace. That was when she realised that Jay turned the radio on.
Hello there, how've you been?
I heard that you're moving to Paris
With that copy comic
I bet he's on it
Her eyes went wide with realisation and she turned to face him, still in his arms.
"It's our song" she smiled, trailing her gaze to his face and wrapping her arms around his neck.
"Dance with me?" A soft whisper erupted from Jay's mouth as he took a step back, extending his hand to her. She accepted and they fell into each other's embrace.
Take me for instance
I hold your tune
While I cast a long shadow
And wait for the moon
They swayed rhythmically to the melody of the song. Their song. The one that was playing in the bar the night they kissed for the first time. The night where everything changed.
"I'm forever yours, you know that right?" It slipped so easily from her lips that she didn't register it. But Jay did. In response, he cupped her cheek gently and said "mmhm... and I'm your man".
Songs:
Willow by Taylor Swift
Copy Comic by Robert Francis
Day 2 of @upsteadofficial's song prompt challenge :)
WHERE ARE THEY?! It looks like they’re in some sort of igloo! But with plants behind them? What are those lantern thingies in the circle windows/tunnels? Any Chicago natives have an idea about where this could be? A spa was the best guess I have heard so far, but I have still never seen a spa or anyplace that looks like this (in real life or on the show). Low key hoping the sneak peek is from this scene so my brain can stop stressing over it every time I look at the photos lol. Help!
My predictions for Upsteadofficial’s March Madness! This is not necessarily what I would choose in all cases, but my best guess at how this is gonna go. I feel like my favorites are different from others’, though, so 🤷🏻♀️. The right hand column was tougher to predict, but idk...I’m kinda thinking 8x04 is gonna win. 🤔😂
Mistletoe
For the 6th day of the @upsteadofficial Christmas word prompt--Mistletoe. (Rated T)
Note: Started this for the Presents prompt but didn’t finish it in time so used it for part of the 6th day instead. Hopefully it’s not too clunky.
“Upton. This has gotta stop.” Trudy Platt all but stomped over to Hailey’s desk. She unceremoniously dropped a small package on her desk. “See this?” She pivoted a bit to show her shoulder badge to Hailey. “Does this say ‘Postal Service’? No. It doesn’t. So stop having these delivered here.”
“Sorry, Sarge.” Hailey replied. Again she offered no explanation. The season would be over in another day and then this would all be over. She slid the package to the far side of her desk without looking at it and got back to work as Trudy moved in to Hank’s office.
“You serious?” Jay asked over his computer. “That’s like the fourth one. Who’s sending them?” He got up to round the corner to her desk but Hailey was faster. Barely looking, she palmed the package and slid it inside her desk drawer.
“It’s nothing, Jay. Really.” She tried for a smile but knew it fell flat. Just one more day. “It’s not important.”
“C’mon, you’re not even a little bit curious?” His brow furrowed. God knows he was. First came flowers. He’d made note of her face as she read the card, (It wasn’t a happy one) and later when he’d gone in to the break room for a bottle of water he saw them crammed in to the small trash can back by the couch. The next day there was a package. She’d checked the return address and slid it in to her bag underneath her desk. If Jay hadn’t been coming from the hallway after finishing up an interview with a suspect he wouldn’t have seen it happen. The next day there had been another package and now today.
“You have a secret admirer?” He asked, half teasing. For the first time since knowing Hailey he’d gotten her a gift. He hadn’t meant to, he told himself. He’d been with Will, killing time while he shopped for Hannah before they went for dinner and drinks, when he saw it. A simple necklace. A leather band with a small gold circle. He’d had it embossed with her initial and did his best to ignore his brother’s smirk as he joined him to pay. Now the thought that maybe there was someone else in her life, someone he wasn’t aware of, crossed his mind for the first time. He tried to tell himself that it was fine, she wasn’t his. But the only thing that gave him any solace was remembering her face at reading the card that came with the flowers. No eye roll—but a deep sigh and a scowl. If there was someone, it wasn’t someone she felt anything good for. That kept him going. Though he still wanted to know what was going on.
“You have a secret admirer?” He’d asked the question and she wasn’t sure how to take it. Was there some jealousy in that question? Concern? She shook it off on the inside. She’d rather not think about it let alone answer it.
“I wish,” she’d joked back and purposely got back to work.
Jay watched her for a moment. She was avoiding the question…and him. Rather than push him away, it only made him more curious, more prone to dig in and find out what was going on with her. He only wanted to help. She should have known better.
The next day brought no new case and one new package. Another slide in to the drawer as Hailey smiled in apology at Platt’s latest delivery. Hailey hoped that the gift card to her favorite coffee spot would soften her up a bit. She traded the envelope for the package and Hailey watched as Trudy peeked inside the card to see what was inside. “Well…” was all she offered before she walked away. But Hailey took it as a win and smiled at her back. She was still grinning as she turned back to her computer.
“Ah, there it is.” Adam clapped once and pointed at her. “Smile’s back, people!”
She rolled her eyes before looking up to see Jay watching her.
“It is nice to see again.”
She could feel the blush creeping up her cheeks so she ducked her head and tried to get back to focusing on finishing the paperwork she swore to herself she’d have done before clocking out for the night. Before she could just have the next 4 days to not think about the worst that Chicago had to offer, the innocent victims, the scenes she was called upon to see how the two factions met. She wanted to block it all out and just ‘be’ at home. Bad tv, sleeping in , a few late nights, these were the things she was looking forward to.
She didn’t mean to be a hard-ass lately but she knew she had been. This time of year, for as much as she enjoyed the majority of it, it was also a time that she dreaded. Knew the push that always came and this year had been no different.
“So tomorrow’s Christmas Eve.” Jay’s voice filtered through her thoughts as it always could. She looked up to him. “Got any plans?”
“Nope.” Her answer was cavalier as she closed a file. “You?”
“Well,” he rubbed at his chin, not nearly as invested as she was in finishing his paperwork before their shift ended. “Will’s working and…..no.” He smiled. “Soooo, would it totally kill your holiday vibe if I stopped over for a drink?”
“My holiday vibe?” she laughed. “Come over anytime, Jay. I’ll be home.”
He grinned and for the first time in a few years, realized he was actually looking forward to the holiday.
The next afternoon found Jay at Hailey’s door. When she answered he found himself having to remember to breathe. She looked like herself, casual and relaxed, but at home that version was so much more her and it took his breath away for just a moment. It was happening to him more often and no matter how he tried to talk himself out of it, give justification to it, he knew he was simply lost in her. He’d finally realized his feelings but couldn’t quite figure out what to do about them.
“You okay?” She was staring at him, running their dynamic over in her head for the millionth time. There were times she thought they were both in sync, that he wanted what she did, to try and take the next step, to see if they could have something good past partners and friends. And then there were others where she was left feeling insecure and wrong and like she was spinning her wheels. She’d had offers of drinks, dinners…..of more, from other men. But none of the guys were Jay. None of them left her feeling like he did when he looked at her like he was right now.
“Yeah….yeah. Merry Christmas.” He offered a half smile as he walked in.
“You too.”
She’d already started on the tequila and had thrown some beers in the fridge. She offered him his choice, and they settled in her living room, and sipped their drinks in an easy silence.
Jay ran a finger around the rim of his glass and looked over to her. “Not too Christmasy around here.” He glanced around the room.
She huffed out a small chuckled and smiled in agreement. “Not usually around.” At his look she explained. “I may have been known to pick up an extra shift here or there if the OT was available….or if not,” she smiled and inhaled deeply. “rent a place in Indiana or Michigan…some place on a lake. Quiet. Remote.” She shrugged a bit.
He looked at her nearly incredulous. “I really don’t know you at all, do I?” He meant it as a joke but shook his head at the information.
“You know me better than anyone Jay.” It had slipped out, immediate, quiet and earnest.
He nodded at her, solemn, quiet. Pleased at the comment.
“Okay then,” he breathed out. “Then what was the deal with those packages?”
He didn’t miss the small lip twitch, the flash of a dark look cross her face. When she didn’t respond, he tried again. “Hailey?”
Finally she spoke. She shrugged lightly. “I thought maybe…when I moved to this place….but my mom is smart.” She chuckled. “No address to send them to so she sent them to the district. They’re just…she never stops trying.”
“What do you do with them?” He probed.
“Donate them.”
“Do you know what they are? What they send?”
“Nope.” She shifted on the couch. “It’s easier not to.”
Jay nodded, trying to understand. “Sooo, nothing to open for Christmas then?”
She smiled a bit. “I don’t need presents, Jay.”
“Okay, that’s a lie.” He teased, reaching for his jacket and rummaging in a pocket. He pulled a small square box, neatly wrapped from it and passed it over to her.
Hailey swallowed hard. “Jay,” she whispered. “You didn’t have to….I didn’t…..”
“No, no, no. It’s not a big deal.” He chuckled and tried to play it down, now questioning his decision to give it.
“Can I…?” She glanced at the package.
“Yeah, of course. Go ahead.”
Hailey deftly unwrapped the paper neatly and Jay saw her eyes widen as she took the white top off the box.The dark band lay against the white cotton bed, the small gold circle shining in the living room light.
Jay found it necessary to start talking. “I just….you used to wear one like it and I saw it and just thought….”
“It’s beautiful.” She whispered, looking from it to him. “Thank you so much.” Her old one had broken off, she assumed, during a scuffle with an offender as she’d tackled him. When she’d gotten back to the district that day she’d noticed it was gone.
Hailey put the necklace on and Jay smiled, proud of being the reason she looked so happy in this moment. They sat and drank a bit for a while before Jay voiced an idea.
“Okay, so we’ve gotta get some Christmas spirit going.” He put down his glass and rubbed his hands together.
Hailey laughed. “I’m not getting a tree on Christmas Eve,” she laughed lightly. “so what are you thinking?”
“Molly’s. It looks like Christmas threw up in there. Like it should.” He grabbed for his jacket. “Whaddya say?”
The bar was packed. Locals having a few beers before going home to be with families, a few cops and fire fighters having a drink between ending shift and heading home, and a bunch of college kids home for break getting together with friends before being held captive by well-meaning family members wanting to know how school was and if they’ve met anybody special.
One of those kids stopped on his way back from the bathroom to do a double take at Jay and Hailey—and ogle Hailey.
“Bruh, you see where you are?” the kid asked. Jay didn’t and gave a mild one shoulder shrug, hoping if he ignored him he’d just move on. But he didn’t. “Better make your move dude, or I’m happy to step.in. Won’t have to tell me twice…though she may want to.” He smirked and grabbed suggestively and crudely at the front of his jeans.
Hailey grabbed Jay’s arm as he went to step up. The kid just smirked again and moved on.
“Let it go, Jay. He’s stupid and drunk.”
He was breathing heavier than normal with the adrenaline that pushed through his veins. “Asshole,” he muttered, looking down the bar to where the kid had joined his friends.
He tried to focus back on Hailey and took a sip of his beer, calming down very little by very little. He took a deep breath and offered Hailey an apologetic smile that she returned with a ‘don’t worry about it’ one of her own. He was feeling better and glanced around the bar again, tipping his head up a bit as he drained the last of his beer. He choked.
“Shit….Jay, you okay?” Hailey was up off her stool and standing close to him, patting him on the back instinctively.
“Yeah….yeah,” he rasped. ”Just went down the wrong way.” He wiped at his mouth, and made a decision, quickly reaching for her hand. Feeling the warm skin and surprising softness of her hand under his, he dragged a quick thumb over her wrist. Hailey froze. She’d been about to sit back down when he’d touched her. She didn’t know what to do or say so waited him out, holding her breath.
He gestured upward, calling Hailey’s attention to the ceiling. When she saw it, she rolled her eyes with a grin and groaned lightly. But she didn’t move.
“Ohhh, you gotta be kidding me.” Her laugh and smile faded as she caught Jay’s eye. His own had faded before hers and now he was just looking at her. Looking at her in that way that she never could name but that sent shivers down her spine nonetheless.
“Jay?” She whispered it softly.
“It’s tradition Hailey.” His voice was low.
She nodded slowly. “Yeah. It is.”
Jay was still seated. He parted his knees a bit and took hold of Hailey’s waist, pulling her gently toward him. Her eyes never left his as she shuffled forward.
He pulled a hand from her waist to the back of her neck and she placed hers on his shoulders.
“We doing this?”
“I think it’s about time. So—yeah.” He huffed out a sly smile, genuinely happy. She leaned in to him just as he gave her neck a gentle pull. The first kiss was soft, quick, and tentative. The second and third were soft and meaningful. Purposeful. The fourth was leading toward hungry.
When Jay pulled back slightly it was to find Hailey looking at him, her eyes bright as he thumbed circles at her waist. Neither said anything with both just enjoying the moment.
“Merry Christmas, Jay.” She smiled.
He chuckled lowly. “Merry Christmas, Hailey.”
She was knocked a bit closer to him by the group moving from down the bar past them, as they headed toward the exit.
Jay held on to Hailey tight as she was jostled in to him. The drunk kid from earlier threw them a look and Jay took advantage of it. “Hey bruh…..thanks!” Jay grinned before sliding a hand to Hailey’s jaw and pulling her in for another kiss under the mistletoe.
Sorry, I’m the anon who sent you the message about doing a madness challenge for 8x11. Definitely meant to send that to upseatdofficial 🤦🏻♀️ You, upsteadofficial and ilithiyarys are my go to Upstead blogs, so I forget which one I’m on sometimes lol. Any-who, love your page and all your posts and thoughts on all things Upstead 😊
No worries Anon! Another challenge would definitely be fun. Not sure what @upsteadofficial has planned for the future, but I know it’ll be a good time for the fandom!
And thank you so much!!! That is such a sweet compliment. So happy to provide Upstead entertainment for everyone. I really am obsessed with those idiots. 🥺😩
Gonna tag @ilithiyarys on this so she sees the love too! Hope you’re having a wonderful weekend Anon!! 🥰🥰