Jay Halstead Imagines

Definitely Maybe

Jay Halstead x female!reader

A/N: this is a spin-off for Maybe,
Requested on Tumblr

Warnings: mentions of death, murder, unedited

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The night you went to Molly's for a drink and met Chicago's first responders has gone and past. At present, you have been in Chicago for about a year now and are really good friends with everyone from House 51, District 21 and the doctors and nurses at Chicago Med.
Of course, you and Jay were getting to know each other and have gone on a few dates which you both enjoyed. Some dates being just at each others apartment because either of you just wanted to stay in.

You could still recall your first date with Jay.

It was December when Jay finally had the courage to ask you out on a date. You and Jay were at Molly's one night and he just blurted it out that he wanted to take you out on a date, after Will had nudged Jay to finally say the words.
"Hey, Y/N, would you maybe want to go on a date with me?" Jay had asked and you smiled.
Of course, you agreed. It was your first time to be in Chicago in December so you were experiencing the blizzard that Chicago has during winter season.
Jay had told you to dress extra warm for your date because you guys would be doing something fun. Later, when you asked some of your friends for some help to get ready for your first date with Jay, they immediately jumped at the opportunity to dress you up.

As a model, you were the type to be able to just wear anything because you always managed to make everything that was given to you look good on you. Though you were one of the rising models in the industry, you were really talented that you brought out the beauty of any product. Because of this, you had a hard time knowing what looked good on you.
So, some of your friends from your agency went to your apartment helped you picked out some pretty hot items you had received as gifts from the brands you had previously endorsed.
Jay had told you to wear something warm so your friends suggest to go with black thermal leggings, a black laced trimmed camisole under a cute Christmas swear, and a long puffer coat, paired with cute winter faux snow boots. The girls did a simple makeup look for you and doing a braided half-up, half-down look for your hair.

Minutes after your friends had left and you thanked them for helping you prepare for your date, someone knocked on your apartment's front door. You knew it would be Jay so you immediately grabbed your purse and opened the door. Jay was left speechless upon seeing how great you looked.
"Hey, Y/N, you rea----?" Jay had tried to say if you were ready but seeing how stunning you looked even if it was just a simple outfit, he couldn't help but admire you.
"Jay?" You asked, snapping Jay out of his thoughts and gave you a handsome warm smile.
"You're beautiful, Y/N. You took my breath away." Jay said to you, causing you to blush.
"Thanks, Jay. Don't worry, you look great too." You replied as Jay just continued to look at you. He wanted to kiss you then and there but this was your first date together and he wanted to be a gentleman to you so he restrained himself from pulling you into him.
"Let's go?" Jay asked after clearing his throat and you nodded. You managed to lock your door while Jay was busy looking at you.

The moment the two of you were outside your apartment building, you couldn't help but say a few words about how cold it was. You were still not used to how cold it could get in Chicago and Jay chuckled beside you. You were definitely thanking your friends for the thermal leggings they made you wear.
"I grew up here in Chicago but I still can't get used to how to cold it sometimes get. Come on, let's hurry to my truck so I could blast the heater on max to keep us from freezing." Jay told you as he grabbed your hand and started pulling you towards his truck.

Once inside his truck, Jay turned on the heater and turned it up so the two of you won't freeze to death. He looked at you and smiled.
"I wasn't sure about this idea but then I thought we could go to Millennium Park and go ice skating and then eat somewhere after." Jay told you his plan for your date and you loved the idea. You have been in Chicago for few a while now but still had not been able to explore and do some sightseeing.
"Love your plan! Just have to let you know though...I have never been ice skating before." You told Jay, who looked back at you with a bit of shock but composed himself.
"No problem. I will teach you how to skate and by the time I'm done with you, you shall be skating like a pro." Jay replied and you couldn't help but laugh.

Later, after you and Jay had arrived at the skating rink, changed into some skating shoes which Jay helped you put on since you had no idea how, you and Jay were finally on the ice. Though currently, you were stuck on the side holding onto the railings since he was still teaching you how to skate. When Jay told you to try to skate over to him, you had managed to do so for a bit until you slipped and fell on your butt. You and Jay were laughing and having a great time. Finally, after some falling on your butt a few times, you finally got the hang of it so Jay talked you into skating with him. He skated backwards while holding both of your hands and skated with him. He didn't let go until he was sure that you wouldn't fall down anymore.
"Hey, I think I got it." You said, seconds later after Jay let go of your hand.
"Yeah, Y/N, you're skating!" Jay said to you happily as he skated beside you.
The two of you skated a bit more until the two of you got hungry and decided to go eat something.
"So what do you want to eat?" Jay asked you as the two of you changed back into your shoes.
"Um, do you want pizza? I actually want to try some of your deep dish pizza since I haven't had the chance to try it." You said to him and once more that night, Jay was speechless.
"You've been in Chicago for a year but have yet to try a deep dish pizza?! Ok, we are going to Giordano's and you are eating some deep dish pizza." Jay said as he pulled you to your feet and pulled you to his side as you both walked in the chilly winter Chicago night.

At Giordano's, Jay ordered for the two of you since you had no idea what was good there, though you did order a glass of lemonade and Jay just looked at you weird because you ordered a cold drink on a cold night. You looked around the place and actually felt some homey vibe to the place. When the pizza was served, you just stared at it and Jay allowed you to admire the beautiful pizza in front of you.
"Okay, Y/N, this is the best deep dish pizza you shall ever taste in your life!" Jay told you as he served you a slice.
Jay was about to give you some fork and knife in case you wanted to use some but then you went right ahead and picked up the slice of pizza with one hand while the other supported the end of the pizza, took a bite and placed it back down on your plate. After a few seconds of chewing, you couldn't help but moan.
"Holy shit, this is good!" You said to Jay who was still watching you eat.
"I told you it's the best deep dish you will ever eat, Y/N." Jay replied and you agreed.

Jay would watch you eat from time to time. He knew it was kind of weird to watch you while you ate but he couldn't help it. You amazed him. You weren't like the other women he met before and he was definitely happy that he finally asked you out. He loved your smile, your laugh, the sparkle in your eyes when you talk about something you were passionate about, and your personality. He was falling in love with you and this was only your first date together. He couldn't wait for the other dates that the two of you would go on in the future. Jay could even imagine the two of you having a future together, getting married, having children, and growing old together. It was at that moment that he knew that you were it for him.

You were his definitely maybe and he was yours.