How It Should've Happened

"It's a Date"

"How much longer until we arrive?" Cas asked hopefully. 

"Two more hours. Sick of me already?" Dean said jokingly. 

"No, I'm just not used to traveling by car. If I flew I could be there almost instantly." At the mention of flying Dean saw Cas's wings give an involuntary twitch. 

"I'm sorry." Dean said earnestly. Cas just gave a small laugh. 

"What's funny?" He asked, confused. 

"Don't be sorry, I know you're terrified of flying." He said looking over from the window. 

"I'm not 'terrified'... it's just not my thing." Cas just smirked at the flustered look on Dean's face. 

"I like it when you blush. It becomes you." Cas said honestly. He opened his mouth to make a self-deprecating comment but any remarks he had, flew from his head so he just said, 

"Thanks." 

"What does this mean? For us?" Cas tilted his head slightly. Us. I like when he says that. Dean thought suddenly. 

"It means that I totally rushed things and we should've gone on a date before I kissed you." 

"So dates and kissing usually go together then?" 

"Yeah, usually. I guess we're not very usual." 

"Dean?" 

"Yes?"

 "Will you go on a date with me?" Dean smiled and tried not to blush for the hundredth time. 

"Yeah. I'll go on a date with you." Cas seemed pleased with that answer so he turned to look out the window again. I'll have to ask Sam about dating, he resolved.

Two hours later it was nearing mid afternoon and they were pulling into the motel where Sam was staying. At the sound of the car he came out to greet them. At first glance, it didn't look like anything had changed and Sam wondered if Dean had chickened out. No, he did something. He thought looking at the pair. They both looked incredibly self conscious. And Dean said something that Sam couldn't quite hear that made Cas look uncomfortable, but in a good way. They walked up to the motel room door to see him standing there. 

"Heya Sammy." Dean said, giving him the usual pay on the shoulder. 

"Hello Sam." 

"Hey Cas. Oh hang on a second." He looked over his shoulder into the room to see Dean putting things down and not paying attention. He closed the door quietly leaving him and Cas outside. "What happened?" Sam asked, looking excited. 

"Well there was kissing, and then a lot of silence in the car and then Dean said we should've gone on a date before he kissed me so then I asked him on a date and he said yes." Cas said matter-of-factly. 

"Back up you kissed him?" 

"No, he kissed me." Sam smiled and shook his head. 

"Then you asked him on a date?" 

"That's what I said, Sam." 

"So what are you doing on this date?" 

"I don't know, I was planning to ask you what I should do. It sounded like I was in charge of deciding where to go." Sam blinked and tried to think fast. 

"Well first we have to work this lead, but I don't know if it's a very good one, then your date. He's Dean I mean, he drinks, he drives his car, he sings along to his old music, he eats a lot of pie and burgers, he's terrified of flying in planes-" Cas held up a hand for him to stop talking.