Halstead Imagines

Halstead Headcanons

A/N: Hey, guys! I wrote some headcanons on my tumblr this week and figured I'd share them with you on here! I'll show the original request and then the imagine. Enjoy! And don't forget to vote and comment!

Request from anonymous: Headcanon of Halstead!sister!reader bring home her first bf?

Jay and Will knew you were bringing your boyfriend, Luke, over for pictures before prom. You told them to be civil. You told them to not go into overprotective mode...but of course, they didn't listen.

You walked out in your pink, poofy prom dress and with Hailey next to you (she had agreed over to help you get ready) and Will's eyes went wide. "You said the dress was big, but I didn't think it was that big."

You twirled. "I feel like a princess."

Jay walked into the room. "As you should. You look like one, too."

You shared a look with Hailey when you saw what Jay was wearing. His blues.

"Jay, don't intimidate the poor kid," Hailey said.

"What? He needs to know I'm a cop."

You groaned. "He knows you're a cop and Will's a doctor. Please don't go all crazy. We're just taking pictures here and then we're going out for dinner. Please be--" The doorbell rang. "--normal."

You walked over to the door and answered it.

"Hi," you said as you pulled it open. Luke was wearing a suit with a white dress shirt and a dark pink tie hidden underneath it.

"Y/N..." he trailed off. "Wow, you look, wow. You look beautiful."

You blushed. "Thank you. You look handsome."

"Thanks, babe." You heard one of your brothers clear their throat from behind you. "Um, this is for you."

He opened the box with the pink corsage and slipped it on your wrist.

"Thank you. I think uh, we should get some pictures before my brothers decide at the last minute to not let me go."

You allowed him inside to two stern brothers and one very happy and smiley Hailey.

"I wouldn't let that happen," Hailey said. "I'd make sure you'd go to prom one way or another." She stuck her hand out for him to shake. "Hailey Upton, nice to meet you."

"Nice to meet you as well, Ms. Upton."

"Please call me Hailey. And, don't be too intimidated by them. I promise they don't bite," she said, referring to Will and Jay.

Luke laughed nervously. "Nice to meet you, sir," he said and stuck his hand out for Jay to shake and then did the same with Will.

"What are your intentions with our sister?" Will asked.

"Oh my God," you muttered. "Will!"

"What? We need to know!"

"I'll tell you," you said quickly. "Get some dinner and go to the dance. Simple. Now can we please get these pictures?"

"But--"

"Jay," Hailey began, "they have reservations. We don't want to make them late for dinner."

"Uh, fine," he groaned.

You took the pictures--Hailey had to help you pin the boutonniere on Luke, so that helped the tension drop a bit--and then Jay started talking about hockey during this. Luke liked hockey, so having a civil conversation about it with your brothers, made him feel a lot more comfortable.