Chapter 1- Ask And You Shall Receive

A few things had to be moved around, and some other projects went on the back burner, but here we are at the start of some Upstead one shots. This was an idea I had a couple of months back and I'm equally glad and excited a lot of y'all supported this. Just like my other one shot story, I'm going to start this off and then I'm handing the reigns over to you. Now this premiere chapter comes from a prompt submitted in the other story. Think of this as a segway, a back door pilot if you will.

Hulachick1102: I NEED a chapter of them actually dating and being together!

So this one is a follow up to chapter 13 of A Prompting Jay Halstead Style. If you haven't, go read it so you'll know the backstory of this chapter. Another adventure is about to begin. Let's do this.

It had been forty days since the shooting, thirty days since he was released into the world, and tonight was the night they'd finally agreed upon. Hailey was standing in her closet, hair complete and make up on point, but the outfit was where she was boggled. He told her whatever was fine, which is the most guy response to date night attire ever. Guys had it easy, just wear jeans and either a button down or normal t-shirt and shoes. Women on the other hand had to deal with everything. Clothing, shoes, jewelry, even fragrance hinge on anything from the aesthetic of the building to what type of food was being served. Everything mattered and all elements had to be weighed. People can complain all they want, but it's a big deal and takes some time to put together the perfect date night outfit, especially when it's the very first one.

Hailey just stared into nothing for several minutes asking the clothing to say something at this point. She weighed dress or jeans, dressy pants or leggings and a sweater. Her phone chimed the fifteen minute warning, the reminder she set to know when to leave. She was behind schedule and had to make up time pronto. The old reliables were selected: leather jacket, tight jeans, a white t-shirt and boots. The realization that Jay's limited mobility was likely to restrict him to something casual struck her as she threw the clothing on. It wasn't that he couldn't get off the couch, but a couple of daily acts and movements were still coming along. She grabbed her purse, phone, key and CTA card before hesitating at the mirror a final time, accepting that this was as good as it was going to get for tonight. It was during the closing of the front door that the butterflies fluttered deep in her gut, which she found totally weird. This wasn't a first date with a stranger, but Jay, her partner of two years now. He was still the same person, and they still had the same relational dynamics, but maybe it was the start of something new, the potential for what this all meant. She shook her head, telling herself she was getting way ahead of stuff. The door was locked at a rapid rate and her late self bolted down the hallway, thankful she chose function over form in the shoe department.

…

It was Friday night in Chicago, and a rainy one at that. The spring snow from a month ago was washed away from the random monsoons of April. The month's hottest fashion accessory was a soaked trench coat paired with blown out umbrellas. It was a silly game counting how many poorly made umbrellas were out in the world. The look on people's faces when they realized their only line of defense was destroyed was an added bonus. It was a ten stop, one train change ride from Hailey's place to Jay's. Over the past month, Hailey had done this trek a couple dozens times now. She could do it in her sleep, and felt she had a couple of times. It became a routine, leaving her place before the sun was up to get to Jay before heading in to work, and then doing the routine backwards at night. Jay pestered her for doing all of that for him, but she fell into loving it. She suddenly, almost forcibly, became a morning person and he was a nice prize for her efforts. Most of the rides over we silent, but tonight was crowded, loud, and wet from the latest random soaking. She did her best to hide the giggle, noting she was the only dry person on the train, before turning to the scenery to squelch her humor.

The rain was dissipating allowing the fog to settle over the city. Lights were extra bright tonight, their reflection against the wet environment acting as neon puddles against the sidewalks and gutters. Hailey concluded that Chicago wears rain well, and any weather for that matter. For example, Atlanta looks crummy in the snow and Los Angeles is dismal in the rain. But Chicago can pull anything off and still be its' perfect, stunning self. It's the greatest city in the world, she concluded amongst the crowded, sopping wet car.

The train switch came and went, the stops clicked off in their normal succession. But Hailey swore things were taking longer that night. Every door opening was met with a foot tap and muttering/praying for things to get moving. Partly because she hated being late, but mostly she just wanted to see him and get this crazy idea of theirs on the road. It was that crazy phenomena where good things take forever to happen and bad things ignore the speed of time. Her cue to jump off arrived and she took it, speed walking and jogging down the stairs. She pushed through the crowds for two blocks before stopping at the entrance of his building and breathing. This was it, too late to turn back. The elevator was making its' descent when she waved to the superintendent, whom she had made a pseudo relationship with in recent days. He joyfully waved back with a greeting, doing a quick and friendly approval of her appearance, figuring out the reason for her presence tonight. The elevator chimed, she got on, and shook off the nerves as the car came to a stop.

"You've got to calm down," she told herself, boldly and quickly walking down the hall. She knocked, had the apology ready to fly out, but the scene on the other side of the door changed everything. She burst out laughing at his unruly hair. It was a disaster, like he rolled on a pillow for twenty minutes. And his face of panic and surprise really sealed the deal.

"Help," he spoke, face growing red over her continuous deep laughs. They stood like this for a minute, Jay hanging on the door while Hailey was bent over and looking for air. She pushed herself in after the second request for assistance, his excuse was that he tried.

"What did you do," she inquired?

"I can't really reach over my head yet so.."

"Ok, ok," she replied, using him past the family room into his bathroom. She was able to piece the series of events together: the hair dryer flung into the sink—still plugged in I might add—, the various hair products strewn all over the counter before ending at brushes, combs, and other odd objects. Clearly his attempt to reach the top of his head was a colossal fail. Upon reaching the end of the story she turned around and giggled, humored at his valiant but failed efforts. Jay shrugged before sighing in disappointment.

"Let's just hurry or we're going to be late." She instructed him to squat down into a crouch that looked like Kris Bryant's batting stance, picking up the product soaked brush and beginning the task of rectify his mop of a head. His hair was so stiff from everything being in it that Hailey concluded he'd end the night with zero hairs left on his head. She'd pull, he'd protest. She'd explain he did it to himself, he'd cave before the process began again. Ten minutes later things were back in their usual place. Jay looked relatively normal and the bathroom was restored to its' former clean glory. Shoes were adorned before completing the final scan. He still looked thin, stiff, and tired but the frailness had all but dissipated. With the scars and IV bruising covered, you'd have never guessed he played the staring role in a near death accident forty days ago. He was a normal guy doing typical things; a happy ending to a crazy last month. She ushered him out of the building before turning around to face the door, hearing the lock click against the key before passing it off to Jay.

"How do you shower," she inquired as they boarded the elevator.

"It's a process," he joked, painting a funny and odd picture in Hailey's mind. They reentered the world, soaking up its' dreary, humid night air before Jay took over the navigating. Three blocks later, at the corner of Washington and Wells, was when Hailey's curiosity spilled out.

"So where are we going?"

"It's a sur.." But he didn't get to finish because at that exact moment, a once still gutter puddle sprung to life thanks in part to a bus. Hailey's cat-like reflexes saved her from the wetness, Jay taking the brunt of things. Her shock lasted for about ten seconds before laughter and apologies were dealt. Jay was a vision of glum, his face dejected as he squeegeed his extremities off before admitting defeat.

"I'm so sorry," Hailey gasped through breaks, Jay just nodding as he processed the unfortunate event. His once white shirt was brown and a thin layer of grit and mud was all over him. People were walking by shielding their scoffs and laughs, and rightfully so. Jay was a mess and there was no way to rectify it. Before the next wave of traffic rolled by, Hailey pulled Jay away from the curb to a corner and began inventorying things.

"Aw I liked that jacket," she commented.

"You did, I've had this since starting in the unit," Jay commented.

"Well washing it should fix things. There's no way you're going out like this." Jay nodded, turning back towards the apartment without uttering a word. Hailey caught up to him and grabbed an arm, linking up and walking in stride with Jay. So much for the uneventful evening. But then again, when wasn't life like that.

…

A crash coming in the direction of the shower made her jump, dropping the soiled articles of clothing in the washing machine and bolting. Bad images of Jay injured or passed out in the shower danced in her head. She knew things were moving too quickly, that he really wasn't ready for that much activity yet. They'd already had the conversation: that he was brushing off things like it wasn't a big deal. It was one night about a week after he came home. The team had just left his place and he was propped up on the couch, staring into nothing while giving off the vibe that things weren't alright. Hailey inquired, he eventually confessed to not understanding the hovering and strange, hesitant looks. That it was all an accident and that people were overreacting. She went off, explaining how close he came to dying, that whether he liked it or not things were going to be different for him and everyone else. From that point on Jay accepted the new way of things, that everyone was processing the horrific event. He accepted help and occasionally inquired on their well being. When they arranged this date five days ago, that little questioning voice was speaking, verbalizing doubts if they were ready for this. Correction, if she was ready to jump back in. Jay was moving on with life, but was she returning the gesture. But then reality returned as her hand was hovering over the door handle.

"I'm fine, it wasn't me that fell." She sighed while rubbing the sides of her head, scolding herself for still having flashbacks and immediately going for the bad things. Jay was fine and he seemed to be getting that much sooner than her, or everyone else for that matter.

"Do you want me to pick out clothes," she yelled through the door.

"What?!"

"Clothes!"

"Oh yeah, just pick whatever. Hang it on the handle. I'll be out in a second." The upper hand was finally hers. Now she got to determine what they were doing and put them on an even playing field, outfit wise. She flicked the light switch on and froze, gasping at the size and depth of his closet. She found herself surprised that he had more clothing than her, and she was under the impression she had a lot. She walked a couple of steps, rummaging through piles and hung up articles before landing on grey jeans, a black t-shirt, white Nikes with a green swoosh and a gray varsity jacket. It paired well with her look, both of them looking like different crowds of high schoolers.

She was in the process of cleaning up the kitchen, her final stop in the house tidying task, when he came out of his room with hairbrush and product in hand, sheepishly requesting her assistance again. The crouch came and went, the poking, podding, and instructions were spoken and obeyed and half an hour later both were back where it all began: the front door. Hailey felt like she'd done this door locking thing before, feeling the bolt click against her hand before returning the key to its' owner.

"You look nice," she jokingly commented as they got off the elevator.

"Oh thanks. I can't take the credit. My stylist picked it out." She laughed in that way he loved: the slight throwing of her head back as everything squished into her bright, vivacious smile. They waved to the superintendent for the millionth time that evening, his face now one of perplexed as he waved back. They stood under the awning of the building, both looking to the other for the next step.

"Are you sure you're up for this?"

"Oh gosh, yes. I would tell you otherwise," Jay verbally exasperated. She nodded, not totally believing him but rolling with things anyway.

"So I take it were not going wherever you intended."

"Probably not. I'm sure our reservation has long since been handed off to someone else."

"So out of curiosity, where were you taking us?" He gave her one of those 'really' expressions, tilting his head to the side as his face met at an eyebrow.

"I'm not telling you. I'll just save it for another date."

"Another?"

"Oh, I was under the impression this was like a five date agreement kinda thing." She playfully squinted, shaking her head through a sarcastic smile.

"Let's see how this one goes."

"Really? Getting shot doesn't get you a second date or sympathy votes?"

"I'm a tough date."

"Oh ok," he played along.

"Fine, I have a backup place. Follow me." Jay extend the crook of his arm, Hailey rolling her eyes before accepting. The two of them strolled down the street, now wary of where they stopped to cross. Date night, take two.

…

The ride to Avondale was entertaining to say the least. The train car was packed with tourists and gloomy residences, all jammed in like sardines going to their various places. Even at 8pm, the city was bustling with night life, driving home the fact it was the beginning of a spring weekend. After months of being trapped and nestled in their homes and office buildings, the universe was giving the green light for people to venture out into the new, reinvigorated world. Fresh air was substituted for the stuff pouring out of heaters and central units. Snow and ice coated sidewalks were now clear, clean paths circumnavigating the edges of the city. Sure, they were wet and crowded, but it was nice to not require twenty layers just to go get a gallon of milk or a hamburger. Every year it seemed that would be the year winter never left, but those April showers brought forth hope that things were changing for the better. In the moment things were crazy, but taking a step back you can't help but see things as beautiful. The changing of the guard was a thing to marvel at.

When they boarded the train, rain and street water free, it became a game of musical chairs. The second people left, five more were racing and dodging, vying for that one, single seat in the whole car. Jay's month of disconnect with life caught up to him as they boarded the train. His seat securing skills were ten miles slower than the average guy. Hailey grabbed a seat for herself, scooting into a corner so Jay could occupy the spot with her.

"I'll stand," he announced, grabbing a section of the railing as Hailey disagreed.

"No, there's room. Just sit." He shook his head as the car rolled away from the station, quickly relearning the art of balancing on a moving train. Hailey sighed and rolled her eyes, realizing his stubborn streak would win every time. They wove through the city, admiring it's beauty in this transitional time of year. Occasionally Hailey would smirk or laugh and Jay would inquire, getting the same reply each time: 'nothing.' She was falling in love with him. She still saw him as that dying, pale white thing lying in a hospital bed, but the little moments of the night were aiding in the erasing of that ten day time period. His hiding of the pain and discomfort was movie actor worthy and she wanted to applaud him for his efforts. He was down, and definitely different, but he was doing his best to emerge from the fog and blend back into the world. He'd come so far in such a short amount of time she could cry. But instead she got lost in his person. The blue eyes darting between windows, the slower blinks when a bump came along, and the shifting of his weight to match the twist and turns of the track line. She wanted to stand and hang onto him, have one of those closing scenes in a movie where the two lovers made out in a public place. But the strict instructions of a doctor, and the threat of losing her seat kept her planted. It wasn't how she wanted things to begin but it was better than the predictions forty days ago.

Their stop was announced over the intercom as Jay held out a hand for her to grab. They stood inches apart, each holding on to the other for support as the ride came to a stop. They were the first ones out, darting and weaving through the hurried people. It wasn't till the steps down to the street that thing slowed down, both of them falling back into their normal speed. They walked across the street before heading down Sacramento to their destination. Hailey had only been out here a couple of times so was clueless as to where Jay was taking her. He stopped just shy of the patio, pointing up to the sign with a wide smile.

"You ever been here?" It was Honey Butter Fried Chicken, a restaurant who's sandwich rumored to be as good as Chick-Fil-A, the inventor of the chicken sandwich. Hailey shook her head, mouth now salivating. Jay opened the door for her, only to be disappointed by the sign at the entrance of the ordering line: 'Out of chicken. We're sorry for the inconvenience.' The frustration was all over his face, the dejection dripping off his movements.

"Is this a sign or something," he finally asked to no one. Hailey started smiling, grabbing for his shoulder and crying laughing into it. The night had gone so not according to plan there really wasn't anything else to do. Jay guided her out of the restaurant before joining her laughing session.

"I'm sorry, this is just so unbelievable that it's expected."

"Yeah," Jay replied through his humor. He embraced her in his best attempt of a hug, her arms gently wrapping around his waist. People walked around them before turning their heads, wondering what was happening between them. Hailey didn't care and she was sure Jay didn't either. It was just another event in the story of their friendship turned relationship. Their thing had always been to roll with the punches and they'd come to accept this way of living.

"I have an idea," Hailey spoke up. She took the lead, briskly walking ahead of Jay towards the El. It required another lengthy ride back into the Loop, but the plus was that she got to stare at him again. A win-win scenario.

…

They were at the Riverwalk facing the River Hotel, Trump International to their right and the glow of the Apple Store apple acting as their moon. A bench was secured and their bags of food dished out between them, creating a median. It was quiet in this little nook of the city. The boats, people, building lights, and honking car horns becoming a show for their untraditional first date meal. People were too consumed with their purchases to notice them sitting on Apple property and they took full advantage of it. The late night joggers wove their way along the Riverwalk's border while parents shouted to their kids to slow down, that the edge was going to come up before they knew it. But all of this was background noise to the excitement of finally getting the date under way. Jay was inhaling food, earning a couple disgusted looks from Hailey who was nibbling at her hot dog.

"Did you eat at all today?"

"Yes," Jay obviously replied.

"I'm starving. I haven't walk around that long in awhile," he continued, Hailey nodding upon realizing the truth in that.

"So when do you see the doctor again?"

"Two weeks, but that's just the first visit. Will said it'll probably be another month before I get reinstated. The lingering arrhythmias and slow healing set things back for a couple of weeks."

"Are you ready to come back?" Jay energetically nodded through another bite.

"I was ready when I got released." Hailey scoffed, knowing she walked right into that one. Images of him walking the perimeter of the apartment danced in her head. Him sitting around watching TV forced out a couple of snorts as well.

"But enough about me. What's up with you? What's happening at work."

"I was sworn to keep thing confidential. That if I told you anything you'd show up at work tomorrow morning."

"No I wouldn't." Hailey glared at him.

"I'd show up tomorrow afternoon."

"Yeah, that's more like it," she replied, earning a groan from Jay as she laughed. After a month of talking about test results and medical jargon, it was fun to just be normal; act like typical thirty-something year olds without a care in the world. This was like their unofficial celebration of turning the page on a new chapter. She watched him gather their trash and search for the closest can, quickly come to the conclusion that it was all worth it. Whatever pain and suffering and roadblock that came in their way was worth it. Because had none of those things transpired, odds are very likely they'd not be where they were right now. Furthermore, she could see herself doing this for the rest of time. It all felt so right, each person falling into their role seamlessly. She couldn't imagine a life without him. That if this is how things were till the end of time she'd be more than alright with that. Her daydreaming caught his attention as he sat back down. There was the smallest amount of a grunt from the discomfort sitting caused but he ignored it, placing a hand on her knee to recapture her attention. She snapped her head around, embarrassingly smiling as he smirked.

"This was fun," he concluded.

"Yeah," she trailed off.

"Next time we'll spring for a dine-in meal."

"What's wrong with a Portillo's combo?"

"Nothing, it's just not the typical date night setting." She shrugged her shoulders, mentally replying she preferred that over every other option.

"So I know nothing went to plan but…"

"Yes, we have made it to a second date night" Jay nodded in victory, giving her two thumbs up.

"And for the record, I liked this. It was everything a date isn't supposed to be and it was fun." Something hit the top of her head, another drop landing on his wrist simultaneously. They both looked up only to be poked in the eye.

"You got to be kidding me."

"It wasn't supposed to rain till after midnight," she replied while grabbing cups and her purse. Jay jumped up first to shield her with his jacket. The two of them sprinted off into the night, doing their best to outpace the watery substance falling from the sky.

I have a confession to make and you must not share this with anyone: I have never been on a date. I've never been asked and I certainly haven't forced someone to take me out. It's just something I've never wanted to do. So I found myself at a bit of a disadvantage with this one but I hope you enjoyed it. The directions have been handed off to you. I'm very excited to see where we're going next.