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Published:
2021-07-29
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The Wedding Date

Summary:

When Jay volunteers to be Hailey's date to her cousins wedding what will happen? Upstead fluff.

Notes:

Hey everyone hope you enjoy this fluffy oneshot

Work Text:

“So you excited for the three day weekend?” Jay Halstead asked his partner as they were heading in for the last day before the mentioned time off. Both detectives had accumulated too much time and were being forced to take furlough. One day a week for the next several weeks.
“Ehh not really.”

“Why not? Oh yeah you got your cousins wedding this weekend. Weddings are usually fun. So why the long face?”

“All my cousins and aunts and uncles asking so ‘why is it that your cousin is three years younger and she’s getting married and you don’t even have a boyfriend to bring to the wedding’. It gets old after awhile. I told them I probably didn’t need a plus one but they made me have just in case”

“Just mention how you are a kickass detective working in a unit that most cops would kill to be in.”

“Yeah but it’s hard to explain what exactly we do without giving my Yia-Yia a heart attack.”

“Then I’ll be your boyfriend.” Jay blurted out. Good job you idiot he thought to himself.

“What?” Hailey was so confused she stopped in her tracks.

“I’ll go with you, pretend to be your boyfriend to get your family off your back.”

“Jay you don’t have to do that.” Hailey said as she put her hand into the scanner to let them into intelligence. “I have to drive like three hours.”

“Road trip.” Jay said “Seriously Hailey I had no plans anyway.”

“You sure about this?”

“Yeah like I said weddings are fun. So you want to make up a backstory? How we met? What I do?” He asked having a momentary flashback to when Erin voluntold him he was going to her reunion and that he was supposed to pretend to be a rich tech guru.

“No,” She said laughing “This isn’t undercover you can be yourself. A cop I met at work.”

As they walked into the bull pen Jay heard a snicker behind him. Once he was safely sure Hailey was out of earshot. “How much of that did you hear?”

“Oh, not too much.” Kevin Atwater laughed “Just the part about you volunteering to be her boyfriend. Wishful thinking?”

“What? No! Shut up.”

“Jay, you got it so bad for that girl.”

It was a rare slow day in Intelligence so Voight was ok with everyone cutting out a little early. Hailey went home and grabbed her bag and the bridesmaid dress before driving over to Jay’s apartment. She knocked on the door and when he opened it Hailey couldn’t help but smile all the stubble that was on his cheeks this morning was gone and a small dot of shaving cream was on his cheek.

“Jay you missed a spot come here.” Hailey said wiping the spot away. “So I figured we could take my car so you wouldn’t have to waste gas.”

Jay grabbed a duffel bag and a garment bag “I mean whatever you want to do I’m cool with.”

The three hour drive out to the hotel went surprisingly quick with the partners talking and Hailey informing Jay about all the various relatives he was going to be meeting later at the rehearsal dinner and the next day at the wedding. They later pulled up at the hotel and when Hailey was walking in she silently hoped she was able to change the reservation.

“Hi I know I originally booked a king bed but is it possible there is a room with two beds available.”

“Sorry Ma’am but between the wedding block and the coin convention in town this weekend we’re completely booked. So two keys?”

“Yes please.”

Jay and Hailey got into the elevator and she pushed the button for the third floor. “I’m so sorry about this Jay.”

“Hailey it’s fine. We’ll figure it out. So you want to go into the bathroom first to change or…”

“I’ll go first. Hailey said grabbing the black and red dress and doing her makeup. The black dress with red flowers went down to her knees. She then applied some lip-gloss and mascara and was ready to go. When she walked out Jay was already changed into a light blue button up shirt and black pants.

“You look great Hails.” Jay said as he took in her outfit “So would you want tie or no tie tonight?”

“Save the tie for tomorrow.” Hailey said as she slipped on a pair of heels. And switched her wallet and phone into a clutch. “You ready to go?”

They arrived at the restaurant when a woman in her mid twenties ran over and pulled Hailey into a huge hug. “You made it!!! I was so worried work was going to hold you up and you’d miss tonight.”

“I know but I made it. Jay this is my cousin Sarah, Sarah this is my boyfriend Jay.” Hailey and Jay both were a little surprised at how easily the word came out of Hailey’s mouth.

“Congratulations Sarah.”

“Thank you and it’s so nice to meet you.” After she walked off Jay asked Hailey “So how much of your family am I meeting tonight?”

“Just Sarah and her parents tonight, no one else in the bridal party is family.”

“Oh so you’re the favorite cousin is what I’m hearing?”

Hailey laughed and lead Jay over to the table. The rehearsal dinner was relatively quick mainly Hailey thought they missed the actual rehearsal due to having to travel from Chicago.

Once they were done the two went back to the hotel room and Hailey pulled her pajamas out and went into the bathroom to change and wipe off the little makeup she had on.

“So I’m guessing you’re getting ready for bed?” Jay asked taking in the clothes his partner had on. Even in grey pajama pants with penguins on them and a black shirt he still thought she looked sexy.

“I mean you can keep watching TV if you want but I’m going to bed. I have to be there at 0730 tomorrow.”

“What?” Jay looked confused “Isn’t the ceremony not until 4?”

“Yeah but joys of being a bridesmaid I have to spend the whole day getting ready. I’m sorry you’re going to be stuck here by yourself all morning.”

“It’s fine I brought a book and I’ll hit the gym downstairs if anything. Also if you have to get up that early I’ll go to sleep too I don’t want to keep you up.” Jay said as he went into the bathroom to change. Once Jay was changed into a t-shirt and sweats they both laid down on opposite sides of the bed.

“Night Jay.”

“Night Hailey.” He said as he switched off the light.

Hailey woke up early the next morning and felt a weight across her side. Realizing that Jay’s arm was across her she tried to slip out from under him.

“No baby, don’t go.”

“Jay, you’re dreaming, go back to sleep.” She felt his arm tighten around her. Her heart did a slight flutter and to be honest she would rather stay there. Also it was way to early for this. Hailey was leaving her car for Jay to drive to the venue so after she was dressed she ordered and uber to her aunt and uncles house.

As she pulled up her uncle informed her that the girls were all getting ready in the apartment over the garage so climbed up the steps with her dress on the hanger in one hand and the bag with everything else in the other

“So for getting ready I got everyone matching pajamas. I saw it on Pinterest and just thought it would look so cute in the pictures. Hailey where is your shawl?”

“Oh crap I forgot it. I’ll text Jay and see if he can bring it over later.”

“So how long have you guys been dating?”

“About three months.” Hailey figured it was accurate enough considering that was when he was shot and she realized she was in love with him.

Around ten am Jay knocked on the door to the apartment. “Hey thank you.”

“No problem, I know you had to get up early so I also grabbed you a coffee.”

“Aww thanks that’s so sweet.” Hailey said as she took the items form Jay

“Hey Jay, thanks bringing her shawl. Don’t the pajamas look great on her?” Sarah said from behind Hailey in the doorway.

“Yeah.”

“I told her now she has a pair to leave at your place. They’ll look great on your bedroom floor.” Sarah said and then walked away

“Sarah?” Hailey said in shock.

“What I meant after you change for the day. Not my fault your mind is in the gutter.”

“Ok, on that note I’m going to take off and I’ll see you later.” Jay told himself it was for effect to sell the whole fake couple thing but he leaned over and gave Hailey a peck on the cheek.

Once it was a quarter to four Jay was entering the venue when he felt a hand clamp down on his shoulder. “Hey, Jay right?”

“Yeah”

“Cool I’m Hailey’s brother Anthony. She kind of threw you right into this fire this weekend with meeting the family huh?”

Jay shrugged his shoulders as he said. “Yeah but not her fault.”

“Still I think everyone is here except our dad. Someone had to stay behind and handle the store.” Jay was relieved to hear that Hailey’s dad wasn’t there just because he knew it would be hard to be polite to Hailey’s abusive Dad.

“Hey Mom, Mike, Yia-Yia, I found Hailey’s boyfriend.” He then shifted his focus to Jay. “Come on you guys are sitting with us during the reception you might as well hang with us until Hailey is done.”

After briefly introducing himself to the other relatives it was time to for the ceremony to start.

After getting ready with her cousin and the other bridesmaids, the ceremony and all the photos before and after she felt like it had been six hours. Finally she was able to head over to the table her family and Jay were sitting at. Hailey’s heart caught in her throat at how good Jay looked in the button up shirt, tie and suit pants. The suit jacket was draped over his chair. Hailey made her presence known by putting her hand on his shoulder.

“Yia-Yia loves me.” Jay looked up at Hailey with a smile “I’m invited over for dinner one night soon. She says I can bring you too if you want.”

“Oh you’re funny Jay.”

“No, I’m going to make him meatloaf.” Her grandma confirmed. “He such a nice boy.”

Then Jay heard the song the DJ was playing “Excuse us Yia-Yia but Hailey loves this song so we gotta go dance.”

“Really Hailey?” Mike asked. “Sucker by Jonas brothers?”

“I sang along to it once at work and he wont let me forget.”

“Three times.” Jay held up the fingers “And twice on the way here.”

Hailey laughed as Jay grabbed her hand and pulled her onto the dance floor. Jay loved seeing her so happy and carefree. Next a slow song came on and Hailey wrapped her arms around his neck and Jay’s hands settled on her waist.

“You look beautiful by the way.” He said to her.

“I look like an eggplant in this dress but thanks.” Hailey said referencing the fact the dress was basically bright purple. She had to admit that the hairdresser did a nice job it was up in a bun with a few loose curled strands hanging down. “You clean up pretty good your self.”

“So did we do it?” Hailey looked at him confused. “No one is on your case about your dating life.”

“Nope, not a single comment.” The two enjoyed the rest of the night dancing, drinking and spending time with Hailey’s family.

Hailey woke up the next morning with her head resting on Jay’s chest. Giving herself a few seconds to bask in the feeling of being so close to Jay she then slid out from under the covers to go downstairs and grab some breakfast from the buffet for the two of them.

“Hey Mom,”

“Hey Sweetie. Grabbing breakfast before you and Jay head back?”

“Yeah it’ll be a lot easier to get him up if I have coffee waiting.” Hailey joked.

“Was a good wedding right?”

“Yeah it was a lot of fun.”

“Who knows? Maybe it’ll be your wedding we go to next.”

“Mom, I think it’s a little early for that.”

“Hailey, it’s obvious that man is in love with you.”

“I think it’s a little early for that.”

“Well a mom knows but ok. Get home safe and text me when you guys are back in Chicago.”

Hailey made her way back to the room and was surprised Jay was already up and dressed. “Hey I brought back food.”

“Great, what time did you want to start heading back to Chicago?” He asked and then sipped the coffee.

“I mean we slept a little late so check out is in an hour and a half so.” She said as she bit into a bagel

“Ok so I’m basically packed so whenever you’re ready. Your family is pretty cool and see I told you weddings are fun.”

“Thanks again for doing this.” Next thing Hailey knew she had closed the distance and was kissing Jay. “Jay oh my god I’m so sorry.”

“No it’s cool.” Jay said trying to lean in for another kiss.

“Jay it’s not cool. Oh god I screwed everything up.”

“Or you could of just made everything better.”

“What?”

“Hailey I don’t know how long I’ve had feelings for you. I just finally figured it out when Kelton was threatening to separate the unit but I’m pretty sure I was just denying it way before that. You saying I would forget you eventually because we had only been partners a few years was when I realized I would never forget you. The thought of not seeing you almost every day was like a gut punch.”

“Jay, I have feelings for you too. That’s what I was planning on telling you that day in the hospital.” Jay smiled and leaned in for a second kiss. What started soft and sweet was quickly turning passionate. “Let’s get home ok?”

The drive back to Chicago was filled with quick pecks at red lights and the tension building up between the two. By the time they had reached Jay’s apartment they were making out in the hallway of the building.

“So it doesn’t count as a wedding hookup if we waited until we got back to your place right?” Hailey asked breaking away from their kissing.

“Nope not at all.” Jay said taking two seconds to get the key in the lock before they dropped their bags as soon as they were in the apartment.

Once they were inside and the door was locked Jay pulled Hailey back into his arms. Their kisses turned more frantic as Jay moved his lips down to Hailey’s neck, she in turn ran her hands down his chest feeling every muscle and then yanked his shirt over his head. Hailey and Jay were yanking clothes off as they made their way to the bedroom.

Two hours later Jay and Hailey were cuddled in bed both still naked from the earlier activities.

Jay was tracing lazy circles on Hailey’s shoulder. “I’m going to cash in on this favor by the way.” Hailey looked at him quizzically “One of my buddies from the army is getting married in two months. How would you feel about taking a few days furlough and coming with me?”

“Sounds good.”