A Certain Someone (Dr Will Halstead X Reader)

Back to Portland pt. 1

it's been two days since the date at the Blackhawks game and you are back at work and thinking about the kiss Will gave you. Your thoughts are interrupted by a text

Tommy: I've arranged Alex's funeral and I would like you to be there if you can

you are saddened at the fact that when you go back to your childhood home it's because you will be going to a funeral. You reply to Tommy's text

(Y/N): I'll try and get some compassionate leave

"Hey (Y/N)," Will says as he enters the staff rec room

"Hello will," you say with a hint of sadness

"What's wrong?" Will asks picking up on the sadness in your voice

"Tommy wants me back in Portland for Alex's funeral," you reply

"Will you go alone?" Will asks thinking he should come with you as a boyfriend

"What do you mean?" You ask a little confused

"I am your boyfriend I should be there for moral support," he says

"True but what would Sharon have to say about both of us leaving?" you retort

"Let's find out," Will says

You get up and go with Will to find Sharon

Five minutes later you and Will are in Goodwin's office talking to her 

"I would like to take some compassionate leave," you say

"Because my brother has arranged Alex's funeral but it's at Portland," 

"how long will you need?" Sharon asks

"one week," you reply

"what about you Will?"

"I'm going for moral support," Will says hoping he can come with

"you both have a week of compassionate leave starting after your shifts end," Sharon says 

"thank you," you say 

___________

Three hours later and you are getting ready to go to Portland. There is a knock on your door, it's Will

"coming," you say as you make your way to the door

"It's ok I can wait a couple of seconds," Will replies

Two seconds later and you have opened the door

"Hey Will, come in," you say starting the conversion

"Are you ready yet?" He asks bringing his suitcase in

"I've got one more thing to pack and I've also got the tickets for the plane," you say as you go back to your room

"Let me help," he says following you

"It's all good," you say folding your dress nicely and you put it in your suitcase

"I'm done,"

"Have you eaten?" Will asks wanting to know if he can make it a date

"Not yet I've been busy getting ready," you reply

"Ok would you like me to cook?" Will asks

"If you can," you reply realising  he wants a date

_______

Seven hours later you are awake in bed next to Will who is fast asleep

"Will wake up," you say shaking Will Awake

He groans and stretches

"Wake up sleepy," you continue trying to wake him up properly

"I'm awake," Will says as he sits up with the blanket wrapped around him

"Ok let's get ready," you say ask you get up

Five minutes later and you are waiting for Will to finish. You are having breakfast on the kitchen bench while you wait. You get a text.

Tommy: are you coming

(Y/N): Will and I are both going and we leave Chicago in 3 hours and we will arrive at Portland 

Tommy: I'll pick you both up when you arrive at PDX

(Y/N): ok see you later

Thirty seconds later and Will is ready and he sits in the seat next to you and you slide him a plate of bacon and eggs 

"thank you," he says as he starts devouring the food you made 

"no worries, just so you know Tommy is going to pick us up at the airport," you reply making sure he knows

"ok," he says between bites of food 

_________

Five hours later and you and Will have arrived in Portland. You are looking for your brother.

"Urg I wish they could design a proper waiting area," you say 

"there he is," Will says as he points to Tommy  

"can you take my stuff," you say passing your bags to Will

thirty seconds later and you have caught up to Tommy and you are giving him the biggest hug possible

"it feels good to be back," you remark 

"but it's in the wrong circumstances though," Tommy says

"and where is Will?" 

"Hello Tommy, your sister is happy to see you," Will says announcing," himself

"let's go," Tommy says

"let me take (Y/N)'s bags for you