Castiel Novak, overstressed big boss of his father's company, horribly rich since birth, still a bachelor but not single anymore, had a problem.

He was about to go on his first date with Dean Winchester, manager at Starbucks, proudly working-class, and, if his kissing was something to go by, very eager to be with him.

Still, Cas was nervous. What if something went wrong? What if he proved himself too snobbish, or too superficial, or even worse... boring?

What if Dean changed his mind? Their story so far had been unconventional and filled with hesitations and misunderstandings. And while what he really wanted was to take Dean to his bedroom and not leave for two days, he was aware of decorum.

First, dating and see if they had something that could last. Then, wayyyyyyyy later, introduce him to his family (his mother last if possible, she was nice enough but not exactly... egalitarian in her views) and finally, hopefully, live together.

He had a very clear image of the latter in his mind, filled with simple moments and maybe pets, but in order to get there, he had to go through the rest and he was, frankly, overthinking it.

So to change his mind, he did what always helped: he went to Starbucks. He had someone to see there anyway.

Becky greeted him with enamored eyes and Cas ignored it as diplomatically as he could. Dean sent him an air kiss in between two customers. Castiel lined up in front of Charlie's counter and waited.

"Hey, here comes the Knight of this Realm. So, did you fire Becky's aggressor?"

"Yes, some time ago now. I'm glad I did. It's always good to hire exactly the right person for the right job. Which leads me to my next inquiry..."

Charlie laughed:

"Always so charming! But I'm not gonna make it easy. I want a real interview."

"Of course, I wouldn't have it another way. You're a professional. I'm not offering you the job out of pity."

Charlie was mellowed enough to finally answer:

"Then send me a date and I'll be there. I hope you guys have a decent operating system. It it's Windows 8, I'm leaving."

"I don't think that's the case, and I can assure you that, were the system inadequate, you'll be at liberty to reinstall the best you will suggest."

Charlie sighed:

"How come Dean managed to resist you for so long? I'm gay and I can still feel the charm."

Castiel, who knew the depth of his timidity, didn't disclose that this was the reason he had developed said charm. And the remark about Dean didn't help matter.

"Hey, what's going on? Something wrong at work?"

"Oh, no, not more than usual, but you see..." He dropped his voice and painfully shared : "I'm not very sure where to take Dean for our first date. I'm afraid I am unqualified."

Charlie looked at him seriously, then patted his arm:

"Don't worry, young padawan, I will show you the way."

Charlie brought his order and they talked a while. After he finished his coffee, Cas was about to leave when he was stopped at the door by a suspicious Dean.

"What were you talking about with Charlie?"

"Her future position at my company."

"And... ?"

"Well something confusing about "padawon" and "jedi masters", I think?"

This had Castiel led back to his table and sat down to be lectured:

"That you wouldn't know Star Trek, I can accept, but come on, Cas, Star Wars?"

"I have heard of the movie."

"Movie-s! Frankly Cas, this is embarrassing. You're even dorkier than my brother."

Hearing about a sibling was a new development Castiel was trying to digest, at the same time as pondering Dean's statement.

"So, you're not interested anymore?"

The look Dean gave him was a hundred years old:

"Dorky and an idiot, I see. I thought all rich-ass guys were full of themselves but you're really really not."

"Having money can indeed inflate someone's sense of importance. I am guilty of it, I assure you. But this is all very new and I have invested a lot of feelings in this." He gestured between the two of them and was rewarded with a smile. He forgot what he was saying and just stared stupidly.

"So have I..." and just hearing Dean say that was overwhelming. Castiel hoped it would stay that way. It was good to feel so alive.

"And for our first date, I am supposed to go to the movie theater with you. I was told you loved it and..."

"By who?"

Castiel was getting better at reading Dean and confessed quickly:

"Charlie..."

"Right." Dean's tone was strong but he looked relieved. Castiel made a note not to hide things from him.

"Okay Cas, new rule. When something's bothering you, you come to me. What is this "supposed to" about? What do you want to do for this date?"

"I don't know..." He gave Dean an apologetic look "I don't know you well enough. What if I pick something that will bore you?"

Dean sighed and shook his head:

"Even if it was, I would still spend time with you. We're in New York, it's easy to find something else to do."

Cas nodded. But Dean wasn't finished:

"I'll give you a few pointers, though. I love pies. And food in general. So any place that sells those, I'm fine with. Unless it's the kind where they give you ridiculous portions that cost an arm and a leg."

"Oh, yes, it is a strong dislike of mine. I have to order twice sometimes to get a decent meal."

"And I like movies, obviously, although I prefer watching a DVD back home with my friends. Relaxing on the couch, eating popcorn and mocking the film if we want, you know?"

"Well, I don't own a TV set..."

Dean munched on his bottom lip, then said:

"I do. How about, for that date, we meet at my place and we watch Star Wars? My apartment is tiny, but if you don't mind..."

"I don't. But only if the couch is as comfy as you suggest."

Dean looked at him frowning and must have noticed the smirk.

"It is and it's tiny too. We'll have to squeeze..."

The tone was so suggestive, Cas stood up and put his suitcase in front of his pants.

"Let's do that, Dean. I have to go now..."

Dean looked down and smiled smugly:

"Yep, I have to get back to work too. See you tomorrow night? I'll text you my address."

"Perfect."

After a quick kiss, Castiel was on the sidewalk, looking for a taxi and thinking very hard about his great aunt Naomi until he was composed enough to push his suitcase away.

He and Dean had arranged their first date. Success.