#I realised that I made their blush way stronger than I'd expected but I kind of like it so I will keep it x'D

[mitamicah]

My entry for @vii-doodles' 500 followers DTIYS on instagram (x) ^V^

[shelby-love]

JAY HALSTEAD

Third and Fourth Wheeling

Requested: yes

Prompts: "It's not a double date. We're just third and fourth wheeling."

Warnings: none

Authors note: I hope that this will meet your expectations! ❤️

"Okay stop whatever it is that you're doing," Will Halstead appears by your side on a hectic afternoon.

"Will I'm holding a cancer patient's charts in my hands," You look at him dumbfounded. Why does he think sneaking up on you in the middle work and telling you to drop everything is a good idea? 

"Give me three minutes," You start counting immediately after those words leave his mouth.

"There's this new restaurant that opened not too long ago." He explains quickly, scared that you might leave before he gets to say it all. "Natalie and I want to check it out but because it's new, you know, they don't want to give us a two person reservation."

You're still not picking up what he's trying to tell you so he continues his train of thought. "I thought you might want to go check it out with us."

"Will I don't want to third wheel." You tell him. As much as you live for him and Natalie, going with them to this restaurant seems a bit odd.

"I promise you that you will not third wheel in any way. Okay you just gotta trust me on this one." The tablet in your hands was forgotten and the only thing on your mind was this dinner.

"William..."

"No. You're coming. End of discussion. Dress fancy." With that, he left you alone at the reception. Chasing after him all the way to trauma 2 would not only be stupid but also pretty unprofessional because that's where his patient is.

With a sigh you started walking towards your own patients, eyes glued to the tablet in your hands.

Usually you're good at avoiding collision in the ED but when your body came in contact with a much bigger and stronger one you had to take a step back to steady yourself.

Luckily you didn't fall to the ground as the person cached you before you managed to do so. "Woah Y/N, you okay?"

Jay Halstead.

"Jay if this is another one of your surprises I'm kind of busy at the moment." Jay and you were friends. You were close to Will and ended up being a good friend to his younger detective brother Jay.

You admit that Jay was a handsome guy. He had everything a girl would want but you were blind to see that he truly has eyes only for you.

His playboy image wasn't necessarily going into his favour. You were protecting your little heart by just not giving him the time of your day. But he gave you all of his.

Whenever he's in the ED it's either for Will, for work or for you. He even gave you flowers for your birthday that was not too long ago.

"Y/N the world doesn't rotate around you," He teased which made you roll your eyes. "For your information I'm here strictly work related."

"Oh, well. Good luck." With a bright smile you stride past him to meet your patient.

You ignore the race of your heartbeat.

***

"Yeah, I'm standing outside freezing." You hold your phone shakily next to your head. In a fancy dress and pointy heels you wait for Nat and Will to pick you up.

"Look we won't be able to make it."

Your jaw drops to the floor.

"Excuse me?" You say.

"But don't go anywhere Jay will pick you up since he's closer to your building than we are."

"You're setting me up with Jay?!" You yell at her. No matter how much you tell them they don't listen.

"Please just bare with me! We needed two more people and the two of you are perfect!" Her voice sounds sincere and you give in like you always do.

"Tell him to hurry." And with that you end the call.

***

Soon enough a sleek black car pulls up and Jay comes striding out. He's cleaned up nicely and you even admit he looks dangerously handsome in his suit.

"Jesus Y/N you're freezing." He says when he comes up to you.

"Nice catch detective." You breathe out a puff of air that turns into small clouds of air.

"Let's go." He places his hand on the small of your back and helps you settle in the car before joining you inside.

He turns on the heater and you see yourself visibly relax. The leather interior of the car starts to feel comfortable and you feel yourself fall in love with his car.

"It's nice right?" He chuckles next to you.

"Huh?"

"The car. You seem to love it." He explains.

"Aah," You smile. "The CPD pays well, doesn't it?"

"The CMD doesn't?" His eyebrow is raised teasingly.

"You don't see me drive this beast around town do you?"

"It's not like you and I hang out." There's something more in his words and you know it. "Except now when we're going on a double date."

You take a deep breath, "It's not a double date. We're just third and fourth wheeling."

"Yeah right. Keep telling yourself that Y/N."

You smile.

***

"Good evening." A restaurant attendant comes up to the two of you when your make your way inside. "May I take your coats?"

While you're a bit stiff, Jay seems to be as relaxed as one could be. He casually helps you take off your coat before handing it to the attendant. Coat check at restaurants isn't something you're so used to, so seeing Jay manouver his way with the fancy lads made you see a whole new side of him.

Coat free you were left in your dress. You didn't miss the way Jay looked at you. No matter how much you tried to deny it, it did bring out something in you.

"Do you want to walk among the fancy people like two people who don't know what they're doing... or will you take my hand and walk with me?"

"You win." With that you loop your arm through his and let him lead you away.

His lean body felt nice against yours. With the circumstances switched up you started looking at him differently. You wondered if this is what Will and Nat planned all along.

Soon you spot them. Both of them look dashing and perfectly dressed. "Wow..." Natalie mouthed when she saw the two of you.

Blush crept on your cheeks while Jay was helping you settle in your chair before sitting next to you.

"I mean..." Will started but lost his words.

"Isn't this the best decision ever?" Natalie piped in.

"I already told Jay this and I'll tell you again... This isn't a double date." You calmly say.

Next to you Jay was smiling from ear to ear.

"Adorable." Natalie giggles before taking a sip of wine. You roll your eyes while smiling.

"Well this is going to be a long night." Will comments.

"Cheers to that." Jay says and the two clink their fancy glasses.

***

All throughout the night you became more and more relaxed around Jay. For the first time you truly forgot about the boundaries you've set to yourself and let yourself get to know him.

He charmed you. Yes. He made you smile and laugh. Yes. He made you feel good about yourself. Yes.

You didn't stop thinking about the times your legs brushed against each others, or the times when he would casually drop his arm around your chair.

By the end of the dinner you did admit that this felt like a double date.

"Let me." Jay gestured towards your coat. Smiling lightly you let him take a space behind you and help you put it on. Your heart raced and cheeks began to flush as you felt him standing behind you.

"Are you driving with us?" Nat asked you. You thought about it for a second before shaking your head.

"You two go ahead. I'll see you tomorrow at work." You tell them before turning to Jay. "Do you mind dropping me off?"

The smile he gave you made you think that he just won the lottery. "Y/N wants to ride with me. Please, be my guest."

His hand on the small of your back doesn't feel foreign anymore. It's nice and comforting.

"So... What do you think?" You're settled in Jay's car once again only with different feelings in the air. The atmosphere was comfortable.

"It went better than I expected." You admit. Chicago during the night was a pretty sight to see, it made you smile instantly without you even realising it.

"What's going on with that smile?" Jay teases. Your cheeks tint with pink as you shake your head.

"Nothing. I'm just thinking." You reply, finding it hard to give him a sassy comeback like you always do.

Soon enough, the car is stopped and you're parked in front of your building. Realisation hits you and you take in the fact that the night is over.

You smile lightly before leaning in to give him a kiss on his cheek as a thank you. "I had fun tonight." You admit.

Something shines in his eyes before he replys, "Yeah me too."

You take it as your cue to open the door and bid him a last good night. Just before you close the car door you hear him call your name. "Hey Y/N."

"Hmm?"

"Do you want to have a drink with me some time?" He asks you. This wasn't the first time he asked you that but the only difference with this one was that you had a change in feelings. He seemed genuinely interested into taking you out for a drink and getting to know you. "I doesn't have to be anything fancy like tonight if you don't want to."

The chill Chicago air doesn't bother you as you lean against the door. "Yeah I'd like that."

Why not give him a chance. After all of the flowers and suprise drop-ins at the ED you could see that he meant it.

Your smile mimics his before you close the door and make your way inside. By the time you're warm again you find yourself thinking about Jay the whole night with a racing heart that followed.

MASTERLIST