In the bunker, you were in the corner of your room, pouring alcohol into a flask. You hear footsteps and a familiar knock on the door.
Sam and Dean waltz into the room.
"Y/N?"
"Yeah, over here." You sighed, putting the top back on the flask.
"Hey, Y/N." Dean greets you, knowing that what you're going through is tough.
"Good, I'm glad you're both here." You sat up from the chair and grunted, still a little sore from previous hunts. "I actually needed to talk to you about something. Um, have a seat please."
"Yeah." Sam sits on the corner of your bed while Dean stands.
"Uh...what's going on?" Dean questioned.
"You know what I'm gonna say." You didn't make eye contact with your brothers, frightened on how they were going to react
"Let me guess, this is where you tell us you're gonna pull the trigger?" Dean shot a no way look at you.
"Yeah, it is." You glanced up, revealing Dean who immediately shook his head no.
"No, you're not putting it that on yourself." Dean stood there, eyes widening at you. "No."
"We don't have a choice, Sam." Your voice cracked.
"Of course, we do. Don't we always?" Sam turned a little hostile at the situation. "I mean, isn't that the point of everything we've ever done, that we always have a choice?" Sams voice was dim.
"He killed our mom!" You yelled.
"I get it. We were mad, too." Or you know what? Hell, we are still mad!" Sam shouts back at you. "And a part of me wants Jack dead -- it really does. But, Dean, we haven't even tried to save him."
"You heard him, right? He actually blamed Mom for what happened." You sternly told both of your brothers.
"He doesn't have a soul." Sam reminded us.
"And whose fault is that?" Dean shoots at Sam.
"Mine." Sam answered.
"No, Sam. It's not-"
"I'm the one who brought him back, and I brought him back because he's family. And then he came back, and he burned his soul off to save us -- you and me. And now what? You, now you, you want my permission?"
Sam stammered at you, holding in the tears. "You want me to say I'm cool with losing him and losing you all at once? 'Cause I can't do that. I won't say that, 'cause I-" Sam sheds a tear down his cheek. "No, I've already lost too much." Sam stood up from the bed and walked out of your room.
"Dean, I-"
"You're killing him, Y/N. He doesn't want you to do it. You killing Jack? I don't know, Y/N." Dean stood up and kissed you on the head. "We'll figure this out in the morning, okay?" Dean grabbed your hand in comfort and slightly let go, following Sam out of the room.