Castiel had never been too familiar with feelings, being an angel didn't require feeling anything, in fact, the fact that he was an angel was the very reason he didn't feel anything at all, which had never bothered him until he realized that he had a choice and that he was ready to make his.
"Sam, can we speak?" Cas asked to a very sleepy and confused Sam as he suddenly appeared in the motel room he'd stayed the night, assuming Dean wanted some privacy since he had company last night.
"Yeah, sure, but before we do, is everything okay?" Sam asked, which earned him a confused look from the angel. "Why wouldn't it be?" The angel asked, tilting his head.
Sam chuckled despite himself. "Uh, no reason, man, it's just uh, ahem, it's 6am, so kind of early to talk...unless it's an emergency or something..." He began.
"Oh. I see... It is an urgent matter. " Cas replied deadpan.
"OK, then spit it out." Sam said, quickly adding a "share with the team" as soon as he realized that had probably sounded a little too literal for the angel.
"It's Dean. I'm in need of assistance." Cas said.
"What, did something happen to him? " Sam asked, immediately standing up.
"Nothing happened to your brother, Sam. He's alright and sleeping as far as I know." The angel sighed.
"OK, so what or why do you wanna talk about him?" Sam asked confused.
"Sam, your brother is the reason I am here, he's the reason I rebelled, and he's the reason I feel anything at all. I believe I care about your brother and... I would like to show him that, Sam... I tried talking, but Dean wouldn't let me..." Castiel replied, sounding so miserable Sam actually could hear what Dean must have told the guy, still he didn't say anything, deciding he should probably let the angel finish before saying anything.
"So I thought maybe it wouldn't be so awkward for Dean if I could show him how I feel with gestures...but I don't know how to do that since I'm not educated in romance. I have read a few books, but none were very helpful. " Cas explained.
"OK, so let me get this straight, you wanna tell Dean how you feel through gestures ? And then what? I mean I wanna help, Cas, I do, it's just.... you do realize that this plan could backfire, right? I mean, I'm not saying Dean doesn't feel the same way you do, I'm just saying he might not know that yet..." Sam began, sighing. "I know that doesn't make much sense, but these things rarely do anyway... I'll help you, Cas, but you gotta be careful not to freak him out too much or it'll blow it in your face before you even have the chance to tell the guy. " Sam said, standing up.
"Alright. I can do that. So how do I start?" Cas asked, eyes widening.
"Well, you can't start today since he's not alone and would probably shoot you if he saw you sneak into his room, which he would, trust me, so start tomorrow. I'll text you with instructions." He tapped Cas on the shoulder, moving to the bathroom.
"Alright, I'll wait." He replied, vanishing.
When his phone buzzled a few hours later, Castiel checked immediately, reading through Sam's text.
"Hey, Cas, so regarding you know what, get him a pecan pie to get started. You can literally bring it at any time and he's gonna love it... and probably love you for it."
Cas appeared at a convenience store, walking down the food aisle and bending down to pick a pie when he felt a hand on his shoulder. "I didn't know angels needed grocery shopping." Dean teased, picking up the only pecan pie there and winking at Cas before moving to the cashier to pay for his pie. He reached down his pocket, pulling out his wallet when he realized Cas was just next to him, already sliding his money over to the cashier. "I have money." Cas pointed out as if it wasn't obvious already, looking at Dean and then back at the cashier as he did so
His first attempt at doing nice for Dean had failed, but he still managed to pay for the pie and Dean seemed happy about it so he figured it could have been worse.
On the next day when Sam texted him telling him Dean secretely liked taking scented bubble baths and while Cas had no idea where he could buy essences or anything of sorts and didn't exactly know what kind of essences he should get for Dean, but he was determinated to make this work today.
Dean was watching some TV, taking a gulp of his drink when he heard the sound of wings fluttering. He wasn't sure what was up with Cas lately, but he figured it was probably just Cas being Cas or Cas trying to fit in, which wasn't exactly a good enough reason for him to start worrying.
"Dean, there is something I need to give you." The angel announced, handing a small green bag over a Dean, which granted him a very confused look from the hunter.
"I was told that you might enjoy these."
Dean opened the bag, frowning as he saw a couple of essences and a couple of fancy bar soaps inside.
"Wow, glad to know I smell so bad even angels are bothered." He teased, chuckling. "So, who told you I'd like these, huh? Was it Sam? " Dean asked, putting the bag aside and pouring himself some more whiskey. "If it was, know that you should get him some bras because he likes that stuff too."
Okay, he figured after so many years living with the guy the fact that he liked taking bubble baths wasn't exactly a secret, but hey, that didn't mean he could go around telling Cas of all people about it. If he was gonna an awkward moment, than so would Sam.
"Did you like it?" Cas asked curiously. Dean didn't seem too happy about it, but somehow Cas didn't think it had something to do with the present itself, but rather with the fact that Dean wasn't pleased about having anyone other than himself know that he liked scented bubble baths.
"I dunno, maybe." He rolled his eyes " I mean, I appreciate the gesture, dude, I do, ok? I just don't get why you're doing this, that's all." Dean said, putting the bottle of beer on the bedside table.
"I wanted to do something nice for you....isn't that something humans do?" Cas asked a little confused.
"Uh, yeah, I guess. just uh, next time you're feeling compelled to do something nice, bring more food or a six pack..or you know, both...just a suggestion." Dean grinned despite himself.
Castiel nodded, hoarding the information for the next day.
Next morning, following Dean suggestion and completely ignoring Sam's text, Castiel brought Dean pie, and some burgers as well, putting the bags on the table as he appeared in their room. He sat at the table, watching Dean sleep.
Every day Cas would bring Dean a gift suggested by Sam, and every single day Dean would accept them as if they were just gifts. He supposed they were just gifts indeed, but he hoped Dean would realize there was an actual reason for him to bring them every day sooner rather than later. Courting Dean Winchester was probably the most difficult task Castiel had ever done, and that included rescuing him from hell and rebelling against his brothers, still if given the chance, he wouldn't have it any other way. He smiled as Dean mumbled something in his sleep, wishing he could be lying beside the hunter, holding him every morning.
Talking to Sam during the past week had helped Cas figure out what Dean liked and on top of that, what he didn't like, and while he appreciated Sam's help, he was conviced that it was time for him to take the wheel as Dean would probably say.
He knew Dean liked porn, and after watching the pizza man spanking and having intercourse with the babysitter he supposed he could see the appeal, but he wasn't sure how to give him something related to porn without being explicit or freaking Dean out as Sam would say, so accepting a nice lady's suggestion Cas got him a dozen red roses.
A few hours later he found himself placing them on the nightstand beside Dean's bed, leaving a note with it, to make it obvious, in case it wasn't already that they were for him.
Dean woke up a couple of hours later, groaning as he sat up in bed. He was so tired it kinda felt like he'd been hit by a friggin' truck, but since the case wasn't exactly a case he figured there was no reason for them to stay in Colorado any longer so the sooner they hit the road, the better. He glanced over at the nightstand, scowling as he saw a dozen red roses there. "What the hell." He muttered, reaching over and grabbing the note attached to it and reading it.
[With love from Castiel to Dean. ]
And then it hit him. OK, he vaguely remember hearing Cas talking about feelings or some other pansy stuff like that, a few weeks ago, but since he was hammered on that day he honestly thought that was just his mind playing tricks on him or something, but apparently he was wrong.
The fact that no one could see him right now, didn't really stop him from rushing into the bathroom to wash his face, which probably had pretty much the same shade as the roses on the night stand at this point.
The next day when Cas suddenly appeared in Dean's car, glancing over at the hunter, he knew he couldn't wait any longer to declare himself. He thinks in a way he already did through the present he gave the hunter the day before, but he needed to talk to him.
"Dean may I ask you something?" Castiel began, still staring at the hunter.
"Yeah, well, you just did." Dean replied, keeping his eyes on the road.
" I wanted to ask, would you accompany me to a restaurant tonight?" He asked, frowning as the hunter began laughing.
"You kidding me, right? I mean, you don't even eat, Cas! What the hell are you gonna do in a restaurant anyway?"
The angel obviously hadn't thought about that before, but the fact that his body didn't need nourishment wasn't the actual reason he usually wouldn't eat. Plus, he was certain Dean would enjoy going to a restaurant.
"I am not kidding you, Dean. I thought you might enjoy going out and eating something other than burgers and pies for a change." Castiel replied.
Dean wasn't sure where the hell that came from, but did Cas just ask him out?
"Uh,I dunno, dude, I think I got something else I gotta do tonight, but uh, I'll let you know." Dean sighed, rolling his eyes as the angel vanished.
He reached down to his pocket, pulling out his phone and dialing Sam's number.
"What the hell are you guys up to? " He began, not even giving Sam a chance to reply before speaking again. "Cas just asked me out, what the hell did you tell him?"
"Hey, I didn't say anything, Dean. Whatever he's doing, is his idea....I mean, I've helped him in the beginning, but at some point he just stopped texting me or just asking for help altogether and I dunno, I thought he'd given up or something. "
"So basically you're parent trappin' me? You know I'm not into guys right? And that this is Cas?" Dean asked, sounding so insulted Sam had a hard time holding a laughter.
"Yeah, and I know, and that's exactly why I'm helping Cas, he may believe the crap you keep telling yourself whenever you look at him like he's the most precious thing in the world, but I don't, Dean. Go on that date. And let me know if you need privacy afterwards because I don't wanna be scarred for life. "
As soon as the line went dead, Dean stopped the car, staring at his phone for a good 5 minutes before dialing Cas's number.
"Hey Dean." Cas greeted a little surprised, which kinda made Dean wonder if Cas actually thought he wouldn't call.
"Uh, about the restaurant thing, I'm in...turns out I'm not actually doing anything tonight so...What's the address?"
"20100 E. Valley View Circle in..."
"Independence, I know... Meet you there." Dean replied, taking deep breath as he ended the call and turning the car around.