Title: Dating 101
Pairing: Dean, Castiel implied Dean/Jo and Cas/Anna
Word Count: 4,510
Verse: This is a drabble in my ‘Happy Endings’ Verse.
Castiel watched Dean from across the room as he attempted to put together yet another contraption for Mary Elizabeth. The youngest Winchester had so many toys Castiel was afraid that one day soon they wouldn’t be able to find the child amongst them.
Joanna and Mary Elizabeth had gone out for a day with Sam, which was precisely why Castiel chose this time to visit Dean. The Angel cleared his throat to alert Dean of his presence. Dean glanced briefly over his shoulder.
“What’s shaken Cas?”
“Shaking? Nothing is shaking.”
Dean faced the Angel and smirked.
“It means what’s going on. Did you need something or you just dropping by to see your favorite god child?”
He shook his head.
“No I am here to speak with you. I require your assistance with a dilemma I am having.”
Dean continued working on putting together his daughter’s toy Castiel shifting uncomfortably behind him. he considered Dean a friend, but speaking of relationships of any kind was new to Castiel and he was unsure of what to say.
“There is a woman I care for and would like to develop a bond with, but I am afraid I do not know enough about today’s courtship methods to do so.”
Dean stopped what he was doing, pulled himself to his feet brushing off his hands as he smirked at Castiel eyebrow raised.
“You want advice about dating?”
“Yes, you have had much luck with woman over the course of the years that I have known you and now you have a family with a beautiful woman of your own. I wish to have a…partner as well. Are you willing to educate me in the ways of, what did you call it…dating?”
Dean scratched the back of his neck attempting not to laugh at his friend.
“On one condition, you tell me who this woman is that has your panties in a bunch.”
Castiel’s brows creased at Dean’s words. He did not understand that reference.
“I do not wear panties. This vessel uses boxer briefs, that it was the tag says. I believe panties are for females only. Unless I am mistaken.”
Dean chuckled, his head shaking as he moved toward the kitchen grabbing two beers out of the fridge and handing one to Castiel before leaning against the counter.
“It’s an expression Cas. You know you’d think with all the time you’ve spent on earth, you’d try to learn some of the popular references or watch a movie or two.”
Castiel opened his beer and took a small sip before placing it on the counter, a look of hope on his face.
“So you will help me?”
“Sure, who’s the woman? Anyone I know?”
“Yes, it is Anna.”
Dean choked sputtering his beer and coughing as Castiel leaned over and patted his back.
“Are you all right?”
“Yes, it is complicated to explain, but Anna and I have a history. Before she fell…”
His voice trailed off and Dean watched as a look of pain crossed the Angels face before he shook it off and cleared his throat. Dean frowned.
“Before she fell what?”
“There is no need to think about the past. Anna and I have both made our mistakes and have come to terms with them. It is time to start anew. St. Valentine’s Day is tomorrow and in the human world I know this is a special day. I have seen the decorations. I’d like to court her tomorrow night and I’d like you to show me how.”
Dean eyes widened slightly as he did the math in his head.
“Son of a bitch…tomorrow’s Valentine’s Day?”
Castiel gave Dean a disapproving look.
“Yes Dean, it seems to be quite a significant day, are you not doing anything special for Joanna? She is a good woman.”
Dean rolled his eyes.
“Valentine’s Day has become way to commercialized for my taste, although I did propose to Jo on Valentine’s Day, had this whole spur of the moment thing set up too, but that was years ago and I only attempted that because she was pregnant with Mary and being all hormonal.”
“So you do not offer gifts on St. Valentine’s Day?”
Dean shook his head.
“We don’t observe Valentine’s Day in this house…but we do celebrate the day ‘I grew a pair and decided to stop being a bitch’ also known as the day I proposed. No wonder Mary Elizabeth’s sleeping at Sammy’s tonight and spending the Day with him and Madison tomorrow. Someone’s getting lucky.”
He grinned and Castiel smiled.
Dean sighed. Sometimes he wondered what Castiel did all day when he wasn’t with him if he wasn’t learning how to assimilate into the human world.
“Never mind, okay you ready for a little dating 101?”
“There are three things to always remember when dating a woman.”
Dean opened his mouth stopping when Castiel took out a small pad of paper and a pen, a look of concentration on his face. When Dean did not continue speaking he glanced up in confusion.
“Really, you’re going to write it down?”
“Yes Dean, this is important to me.”
“Gotcha. Three things to always remember. Women like a man with confidence, so don’t go in there bumbling your way around a conversation and trying to make small talk. If you have a goal put yourself in a position to achieve that goal. Sort of like a planning out a battle strategy.”
Castiel nodded listening to Dean’s word with great focus.
“Woman like feeling like they are the only thing you can see even if it’s not true, pretend it is that’s what I used to do. Make them feel special, like they’re the only person in the room with you or something. You don’t need to pay attention to everything they say as long as you can catch onto the gist of the conversation.”
Castiel stopped writing as he looked up at Dean.
“But I enjoy talking to Anna; I do not wish to pretend to listen.”
“Cas, would I steer you wrong?”
His brow creased.
“I suppose not.”
“And last, but certainly not least always carry a condom on you or you’ll end up with a crazy rugrat like Mary Elizabeth.”
Castiel glanced over his list before looking up at Dean with a smile.
“This is all I need to know?”
“Pretty much. Listen Jo won’t be home for a while how’s about I run you through what your night should look like and any questions that pop into that little angel head of yours you can ask.”
Castiel nodded putting down his pen and pad.
“This sounds like an excellent idea.”
“Great. Let the lessons begin.”
Castiel followed Dean out of the kitchen with a light smile on his face, feeling less anxious about the whole dating thing. He trusted Dean to help him with his problem, if anyone could teach him how to date it was Dean Winchester.