I'll Paint You Wings and Set You Free

Up in the Stars

(Dean's POV)

What the hell just happened? Castiel just asked me on a date and I just said yes. The total jock of the school asked the new kid, who was an outcast, out on a date. What. The. Hell.

Well I had to get ready physically, even though I was sure not ready mentally. I showered and threw on some clothes I deemed as decent enough for wherever he was taking me. I didn't own much clothing in a color that wasn't black, but I managed to find a maroon dress shirt and black tie, and black skinny jeans. I didn't have any dress shoes other than the pair I wore to my mom's funeral when I was five. So, I threw on my converse; the maroon pair to match my shirt. I spiked my hair with some gel and went back to my room to contemplate how I figured this would go down.

I didn't know what I was going to say when he picked me up, and I sure as hell did not know what he would say. For all I know, he could have been dared by some of his stupid jock friends and then stand me up. But, he seemed pretty genuinely terrified and caught off guard by himself when he asked me out. I was terrified too, of course, just for a different reason. He was at my house, even though I had just kissed him. Not only once, but twice. 

I checked my phone. 6:50. Castiel should be here in about ten minutes. I ran upstairs to brush my teeth and as soon as I was finished I heard the doorbell ring. I rushed down the stairs and flung open the door.

"Hey, Castiel," I said in greeting. "I just have to grab my coat, so hang on a second."

I bounded up the stairs to my room to mentally prepare myself again, and snatched my coat off of my desk chair. I almost tripped on my way back down the stairs, but I managed to catch myself on the railing. 

"Okay, Dean?" Castiel said, standing. "You ready to go now?"

"I guess so," I said nervously.

We headed out to his car, which was still the awesome '69  Charger, and he rushed around to the passenger side to let me in before I got the chance to open the door. 

"Such a gentleman," I said with sarcasm oozing from my tone.

After shutting my door, he ran back around to the driver's side and started the car. We drove for a few minutes in an awkward silence neither of us knew how to fill. Finally Castiel put on music and bobbed his head along.

"Wait, you like this band?" I asked, recognizing the song.

"Yeah, I love All Time Low!" Castiel responed enthusiastically. "Plus, this is, by far, my favorite song by them."

The song was Paint You Wings. Castiel was humming along and drumming his hands on the steering wheel.

"Huh," i muttered under my breath, though I didn't think it was loud enough for him to hear.

"What? Can't a jock like a band like this?" he barked defensively.

"I'm not saying that. I just mean that you don't look like the type that would listen to, like, punk music," I retorted as I held up my hands in defense. I changed the subject. "Anywhoo, where are we even going?"

Castiel let a small smirk flash across his face and kept looking forward. "You'll see."

(Castiel's POV)

Dean kept pestering me with questions about where we were headed, but I wouldn't give him any answers. On my drive over to his house, I called Anna and told her to set up a picnic at a park around thrity minutes from his house. She told me she would make sandiwches and steal a bottle of chamagne from our dad. The park was in walking distance from our house, and not exactly a half hour from Dean's but I needed to give Anna some time. The best part about Dean continually asking me where we were going, was I got to hear him say my name. It sounded good rolling off of his tongue. Plus, he used my full name instead of Cassie.