"THAT'S your big plan Sammy? Tell him how I FEEL?"

"Look Dean, you're not the kind of guy who's going to court Castiel. I don't have any other ideas."

"Oh my God, did you seriously just say "court?"

"Yes Dean I did, would you rather I have said woo? Because you wouldn't do that either, and you should remember that I'm here to help you ... not get yelled at. So if you don't settle down I could leave you to this yourself. Or maybe you could call one of the girls from work and ask.."

"Noooo no , I'm good ... sorry Sammy I just don't know anything about this sort of thing. I've always been so good at you know.. not dating. But this stuff... I've just never had it this bad. Not even for Lisa senior year."

"I know Dean, listen ..I don't know what to tell you unless you'd be willing to .. okay not court but to date him.. romance him.. things like that. That's how relationships work in my experience."

"Okay fine so your best advice is to just ask him out? What if he says no? What if he thinks I'm weird or something. Sam I can't be around the guy 24/7 and have it be awkward."

"Dean he's not going to say no, just ask him out to dinner and a movie ... NOT a group thing ,NOT a friends thing... make that CLEAR! I know you ... you'll fucking chicken out and ask him like you are hanging out...instead of an actual date. Here practice with me... Castiel, would you like to have a dinner date with me sometime?"

"Oh my God! can't I ask him in a way that doesn't make me sound like a teenage girl?"

"No, because if you don't say the word D.A.T.E. everything out of your mouth either sounds like an invitation to chill or screw... either way not okay!"

"Fine... Cas, would you like to have dinner with me this weekend?"

"Nope sex offer... I didn't hear the word DATE Dean!"

"I said dinner, how does that make it a sex offer?"

"Trust me, I'm emotionally scarred from seeing that look in your eyes when you said it... I might need to go shower before I leave."

Both men take a deep breath before continuing.

"Okay look man, let's just say that you ask him like that... he accepts.. you have dinner together, you think it goes well so you bring him back here... do whatever it is that you do to get him into bed.. and he leaves.. Now.. let's say he thought that was an invitation for sex... and you thought it was a date...so you ask him out again, just like that... and lets say he's less of the wonderful person he really is and accepts it all over again... do you not see the problem here? Pretty soon you're gonna think you're in an relationship with the guy and he's gonna think you're fuck buddies..That's not going to be good for either of you! I'm serious Dean, if you want the best possible chance at not screwing this up you have to say the word DATE!"

"Fuck I'm screwed.. this sucks."

"Here try this it sounds less... formal or girly in your words... Just say Castiel, would you like to go out with me this weekend, on a date."

"That sounds a little better.."

The doorbell rings and Dean's hands rub together excited to get their pizza inside.

"Cas would you like to go out with me this weekend, on a date." He mutters to himself as he opens the door.

Instead of seeing the delivery man though, he sees Castiel.

"What?"

"Uh. Nothing, I thought you were the Pizza Man."

"Oh, well technically I am. He delivered it to the wrong house and I thought I'd bring it since I was returning your borrowed clothes anyway. I'm sorry to have interrupted your... plan?"

"Oh no no .. um .. no you didn't interrupt anything! Come on in, it's freezing out there."

"Really Dean, I just came to return your clothing. Here enjoy your pizza."

"Castiel is that you?"

"Yes, Hello again Sam."

"Hey man, why don't you come in an join us for pizza. Dean won't eat anything with vegetables on it so we had to order two. There's plenty of food."

"I really should be getting home, I didn't mean to invade your evening."

"Dean here take the pizza in before it freezes and we'll be inside in a minute."

Dean looked at Sam like he could have killed him, but did as he was asked.

"Listen Cas, I can't tell you what that was... it's against the brother code.. but I assure you that it's not what it looked like. Dean has no desire whatsoever to date the pizza delivery kid. He was practicing for someone else... I can't tell you who.. only that you shouldn't worry and I'm sure you'll find out soon enough. So please just join us for a little while... If nothing else it will save me from an entire evening of a mopey Dean.."

It was pretty obvious that Sam meant Castiel, but he was still a little wary. He couldn't really believe that Dean had any intention toward dating him. But he followed the giant of a man inside anyway. Partly pleased to see Dean just as flustered as he managed to be every single day, partly cursing himself for not just letting the damn pizza boy bring it over.

They make polite conversation while they eat their pizza and even end up laughing quite a bit between the three of them. Castiel can see the teasing nature between the brothers, and finds it very similar to the one he has with Gabriel. You know, except they love each other... He shouldn't think things like that, he knows Gabe loves him he just has very weird ways of showing his love.

"I'm gonna go call Ash, see if he's got that stuff done for me yet... I'll be back in a little bit guys."

Sam was hoping that would give his brother the push he needed to make his move. Even he could understand not wanting to ask someone out in front of your brother, or in his case anywhere NEAR your brother. So he left them alone and went upstairs.

It was a little awkward at first, both men wanting to address the obvious elephant in the room but neither knowing where to start. Dean because he was emotionally handicapped ,as Sam would call it. Cas because, he was terrified of being rejected by someone he had to see nearly every day. So they sat there... in awkward quiet. Finally one of them broke;

"Would you like to have dinner with me sometime?"

"You mean a DATE right?"

"Yes, I mean a DATE."

"Then YES! I'd love to."

A/N: Who broke first? huh? Who do you think it was.. .review and let me know... to be honest I'm not sure yet... Maybe you can help me figure it out!