Imagine: you and Dean go on a walk through the woods to clear your mind. This will be written in first P.O.V*

I finish the last touches on my neatly made bed. It takes everything in me not to jump back in, pulling the covers over my head. I take a deep breath and sit at the foot of the bed, pulling out my phone.

I still haven't heard anything from Jack. The last time we spoke, I went off on him for something stupid; with all the stress I've been dealing with lately, I tend to do it to everyone. I know none of them to deserve it but lashing out comes naturally to me.

A knock echoes throughout my room, interrupting my thoughts.

"Yeah," I call out, watching Dean open the door and peeking into the room.

"Hey, I'm bored; wanna take a walk," he asks as I raise an eyebrow at him.

"Where's Sam," I question, putting down my phone.

"Asleep,"

I smile, nodding and putting on some tennis shoes. I follow him out the door into the cool, crisp autumn air. I take a deep breath taking in the beauty of the color-changing trees surrounding the bunker.

"Beautiful isn't it," Dean and I start walking along the gravel path.

"Yeah, it's crazy how such a beautiful world has so much evil in it," I comment, kicking some rocks underneath my feet.

We continue down the path letting the comfortable silence sit between us. Thoughts race my mind about Jack, the guys, the future, and even college. Would Dean be upset if I went to college, or would he be ecstatic?

"Hey, D," I speak up, breaking the silence.

"What is it, kiddo," he looks at me, knowing something's up.

"I've been thinking about it a lot,"

"Oh boy," he playfully rolls his eyes which makes me shove him, chuckling.

"How would you feel if I went to college," I look at him, but he doesn't show any expression.

"I don't know if I want to go to college— I don't even have good grades, but it was just on the table. I don't know what I want to do, but I think-"

"Hey," he interrupts me putting his arms around mine.

"No matter what you decide, I will always be proud of you. There's nothing you can do that can change that. I would miss you like crazy, but I am your number 1 cheerleader," he looks at me, kissing my forehead.

I smile, feeling nothing but love for him. Dean might be a hot head, but he always knew how to comfort me when I needed it the most. We continue down the gravel path, talking about life itself.

With everything going on, Dean and I haven't sat down to talk. He's either busy on a hunt, whereas I could be teaching Jack about the world. It's nice to catch up with you finally.

"Y/N," he puts his arm around me.

"Yes, big bro," I grab his hand, holding it.

"You know I love you, right," he states matter-of-factly.

"Yea," you reply, confused about why he brought it up.

"I want to ensure you keep that in your pretty little head. I know you're stressed, but as I said earlier, I'm your number one cheerleader," he tells me.

"No chick flick moments," you look at him grinning.

He laughs, nodding.

"Good one," he shoves me, a little proud of my comeback.

He might be hot-tempered to most, but I see a side of Dean nobody enjoys seeing. And I wouldn't trade it for anything.