#awkward!cas

Castiel licks his suddenly dry lips. “Hi,” he says, then remembers that this is the man who is worth billions and who has power over his literal job (and therefore his living situation and eating situation). “I’m, uh, from IT? There was a problem?” 

Mr. Smith blinks at him for a long moment, and Castiel wonders how he could have possibly screwed up so soon. Then he gathers himself and gestures towards his computer. “Yeah. I got here first thing, and it won’t turn on.” Castiel chances a surreptitious look to make sure it’s plugged in and comes back with inconclusive results. “Think you can do something about that, Steve?” 

Heat floods Castiel’s cheeks. He hadn’t really looked this morning when he grabbed at his nametag (he hadn’t really looked when he grabbed for a shirt, a fact of which he is almost painfully aware of now that he’s standing in front of Mr. Smith), and of course he’d grabbed the joke. 

“Castiel,” he mumbles, and immediately regrets it. What does it matter that Mr. Smith knows his name? He’s never going to see the man again, so really why does it matter? (He wants to hear that lovely, deep, gruff voice say his name, his full name. Just once.)

“Your nametag says Steve.” Castiel knows the look that’s starting to spread over Mr. Smith’s face. It’s the one that he’s seen all of his life, the one that says Uh-oh, now I’ve gotten myself into a conversation with this freak, how can I best extract myself from this situation. It hurts, much more than it should, to see Mr. Smith start to look that way. 

“It was a joke,” Castiel mumbles. Warmth spreads down his neck, sparking a nervous little sweat. “My name is apparently difficult for people, so they gave me this tag to make things easier.” 

Mr. Smith’s mouth purses. “Well, that’s a douchey thing for whoever to do. Cas-tee-ell.” He lingers over the tee, rolling it on the tip of his tongue, and goosebumps prickle on Castiel’s arms. “It’s a mouthful, but it’s not hard.” 

A different kind of warmth suffuses through Castiel. It starts at the center of his chest and slowly spreads outward, like the eggnog that he had last Christmas at the company party. It’s tingly at the edges. 

“Well, that’s not what everyone else thinks,” Castiel says, to try and diffuse the heat flooding through his body. 

“Yeah, well, nobody thinks how I think.” Mr. Smith keeps his eyes focused on Castiel’s face. There’s something intense in his eyes, and for once, Castiel finds himself on the uncomfortable end of a staring contest. “‘S why they gave me the gig in the first place. ‘Innovative ideas’ or something like that.” He chuckles, and there’s something bitter in the sound. “I don’t think they realized that I have maybe one good idea every couple of years.” 

“I don’t think that’s true,” Castiel blurts, before he can stop himself. He has no real basis of comparison for his statement; he knows next to nothing about Mr. Smith. “I just mean,” he stammers, “that if you start doubting yourself, then you’ll never know what you can do.” 

The advice rings as hollow coming from his mouth as it did coming from the mouths of every advisor and guidance counselor he ever had. Mr. Smith’s mouth twists in a sardonic little smile. “Supposed to breathe new life into this company, and I can’t even get the damn computer going.” 

“Oh!” Suddenly remembering the reason he’s in this dream of an office, Castiel moves forward. “I can probably help with that.” 

He steps in close to Mr. Smith (too close if his sudden blush and recoil are any indication) and fiddles with the mouse and monitor. The screen remains dark, which Castiel is almost glad to see. At the very least, it tells him that Mr. Smith isn’t an idiot. He follows the cords and finds that at the very least, the computer is plugged in. He kneels under the desk, sorting through the various tangle. 

“Ok, the person who put this together is an idiot,” he murmurs, tugging at a cord. 

“I put it together.” 

A cold spike of fear jolts through Castiel. Why, why, why does he always speak without thinking? Why can’t he be like a normal person, who had a modicum of tact, why can’t he manage to hold it together in a conversation long enough to interact like a regular person? Why is he such a disaster of a person? 

He bashes his head on the top of the desk as he scrambles out from underneath it. He glances up at Mr. Smith (tries not to concentrate on the visual aspects of this particular scene: him, on his knees underneath the desk, Mr. Smith, on his chair, looking down at him with a smoothly amused expression). “I’m sorry,” he says, hopefully in a garbled amalgamation of the English language. “I didn’t mean to...”

“Calm down, Cas, it was just a joke.” Mr. Smith’s face turns apologetic. “Apparently not a funny one.” 

Relief floods through Castiel, at odds with the throbbing pain in his head. “I just meant...the person who set up the computer did it wrong. The wires are shorted out.” He rubs at the back of his head as he glances back down. “It’s a simple fix, shouldn’t take me more than five minutes.”

“Oh.” Mr. Smith’s mouth (Castiel really shouldn’t be staring at Mr. Smith’s mouth so much, has Mr. Smith noticed how much Castiel has been staring at his mouth? Is Mr. Smith aware that he has a mouth which is very stare-worthy?) drops in a frown. “So quick?” 

“Well like I said,” Castiel grunts as he shimmies back under the desk, “it’s a quick fix once you realize what you’re doing. The person who set this up was probably just trying to go too fast and made a mistake. Or something. Who knows.” He doesn’t want to throw a member of his department under the bus, but he doesn’t want to lie to Mr. Smith either. 

“No, I just mean...” Mr. Smith taps his fingers against the desk. “Listen, do you want a cup of coffee or something?” He gestures towards the gleaming coffee machine on the counter. 

“I don’t know.” Castiel stops working and pokes his head out from under the desk. “I don’t want to be late.” 

Mr. Smith laughs. The sound is round and rich. It fills the room and sends little sparks of delight dancing down to his fingertips. “Who’s going to narc on you? You think you’re going to get in trouble with the boss?” 

“I mean...I guess...” Castiel can’t help but smile at Mr. Smith. 

“Come on, Cas. Give me a break here. Have a cup of coffee.” 

“I’m really glad you got the job,” comes tumbling out of Castiel’s mouth. Which is bad enough, but then comes, “You’re much better looking than Mr. Adler.” 

A dreadful silence hangs over the room. Castiel hopes his words will fade, but they linger between them like skywriting, scrawled in neon. His brain decides to come back online now, with thousands of worst-case scenarios. 

Mr. Smith fires him for sexual harassment. 

Mr. Smith presses charges against him. 

Mr. Smith ensures that Castiel Novak never gets a job anywhere in the industry ever again. 

Castiel ends up homeless and alone, ridiculed by everyone, and has to move in with Gabriel, possibly ending up working as a production assistant in Gabriel’s porn company. 

Then Mr. Smith laughs. It’s not a mean sound; it’s delighted. He pinches at the bridge of his nose, still laughing. Even after the sound fades, his shoulders still shake with mirth. When he opens his eyes, Castiel thinks there are actual tears in them. 

“I mean, that’s a pretty low bar to set, but I’m glad that I made it over.” Mr. Smith chuckles. He’s still laughing as he makes his way to the coffeemaker. He pushes a few buttons, then leans against the counter. “Stay for coffee, Cas. Please,” he adds as an afterthought. 

Castiel thinks of his tiny cubicle, crowded together with dozens of other small boxes, in a stifling environment screaming with the sounds of computers and copiers. He thinks of Mr. Smith’s smile, the strange kindness in him, the thoughtfulness with which he said his name. 

“I can stay for coffee, Mr. Smith.”

Mr. Smith turns around, one eyebrow raising at the formality. “Call me Dean,” he says. 

Castiel turns the name over in his head several times. It’s simple, direct, yet oddly complicated. It suits the man in front of him. 

“Hello, Dean.” 

No matter how strange he was or how weird his replies usually were, you were happy to have the extra help on the night shift, especially this particular Sunday thanks to a huge local football game. There was triple the normal amount of patrons, and it was all hands on deck to make sure everything went smoothly. The store made a lot of money, which was great, and the night also went very fast, which was nice for you and Steve.

Until your boss told you to do inventory on the stockroom before you left. You’d be paid overtime, but inventory was no fun. At least Steve would make things go a little faster.

After slipping the deposit bag into the slot in the safe, you joined Steve in the stockroom and chuckled softly to yourself at how overwhelmed he looked. His blue eyes were darting across the paper on the clipboard, and he looked like he was trying to set it on fire with his mind.

“Okay,” you broke his concentration, making him jump, “have you ever done inventory before?”

Slowly, he shook his head and passed you the clipboard.

“Right, no worries. Nora mentioned you’re a fast learner and a hard worker, so this should be a piece of cake with the two of us working on it,” you muttered, looking over the items listed on the inventory form. Looking up at him again, you smiled, trying to ease his nerves. “How about you watch me do it a few times, then I watch you, and if you’re comfortable you can start at the far end and work your way up?”

“That seems agreeable,” he replied with a stiff nod, blushing slightly when you locked eyes with him.

The next hour went by in a flash. Steve learned the inventory process in a matter of minutes, and was able to get almost half of the far back side of the stockroom tidied and inventoried by the time you finished the big shelf in the front with all the fast selling items that need to be restocked daily. Steve politely returned any small talk, but rarely offered any facts about his own life, including where he lived. Trying not to pry was difficult, but mysterious men were always intriguing to you.

Focusing back on the next section, you noticed something large stuffed behind the metal frame of the shelf. Reaching behind it, you grabbed the item and began to wiggle it to pull it free. Of course, part of the shelf toward the back near the wall was broken and sticking out, and when you finally yanked whatever was stuck free, your arm slammed against the broken piece of shelving and gave you a pretty nasty gash that began bleeding profusely.

“Ow, fuck!” you hissed, dropping the item you pulled free - which appeared to be a rolled up sleeping bag - and covering the cut with your other hand. “Steve?!”

“Yes?” he replied as he walked toward you, his eyes going wide at the blood pouring out from between your fingers. His cheeks turned red when he saw the sleeping bag, but he looked up at you and said, “I will get the first aid kit!”

Slumping to the floor, you kept a tight grip on your arm, ignoring the throbbing pain that was making you grit your teeth in order to not scream. Steve came back a few moments later with the large first aid kit and immediately went to work. He was methodical, making sure the bleeding was under control before studying the wound. The graceful way he was moving could only mean one thing.

“Do you have medical training?” you asked, curiosity piqued.

“I,” he cleared his throat, “I used to be a… a soldier. Saw how some of my friends patched themselves up and learned, even though I didn’t usually get hurt.” He gently moved your arm and rotated your wrist back and forth. “It doesn’t appear to need stitches. I will clean it and bandage it.”

“Thanks, Steve,” you sighed, thankful you didn’t need a trip to the emergency room. “I’m happy I got my last tetanus shot,” you joked, earning an awkward half smile from him as he grabbed the rubbing alcohol from the kit.

“This is going to sting,” he said softly before pouring the rubbing alcohol directly onto the wound. Pain sparked making your vision splotchy and you hissed, cursing quietly as he began dabbing the wound with some gauze. “Sorry.”

“S’okay,” you mumbled through gritted teeth. Thinking back to his reaction to seeing the sleeping bag, you had to ask. “Steve,” he looked up at you and you pointed to the rolled up fabric, “is that yours?”

“Yes,” he admitted quietly. “Nora is already aware of it, and sometimes when I work late it’s just easier to sleep here instead of walking home. To my apartment. That I own.”

His rambling only made you smile and place a hand on his arm, stopping his movement as he was bandaging your arm. “It’s okay. We’ve all had rough times. If you need a place to crash, I have a pretty comfortable couch. I can guarantee it’s a lot more comfortable than a sleeping bag on concrete.”

Leveling his beautiful blue eyes on you, he gave you a suspicious look, glanced down at your arm, and blushed again. “I suppose you are correct.”

Once your arm was bandaged, Steve helped you to your feet and steadied you when you wobbled slightly by placing his hands on your hips. His entire body went stiff when there was only a few inches of space between your bodies, and you grinned.

“You’re new at this, huh?” you asked, pulling your bottom lip between your teeth, eyes darting from his plush lips back to his eyes.

“Is it that obvious?” he exhaled shakily, huffing a small laugh.

“Only a little,” you giggled, taking a half step forward and pressing your bodies together. “I was thinking, maybe we could take a break from inventory? I can teach you a few things about… work ethic.”

Steve narrowed his eyes at you and tilted his head, but when you stepped back and pulled your shirt over your head, his eyes almost popped out of his skull. “Oh! You… you’re talking about being intimate.”

“Yeah,” you murmured, untucking his white shirt and sliding your hands over the expanse of his surprisingly toned stomach and chest. “If you don’t want this, we can stop.”

Steve actually stepped back slightly and contemplated, but when he shook his head and started unbuttoning his shirt, you let out a breath you didn’t know you were holding. His movements were jerky and awkward, but you pushed the shirt off his shoulders to the floor and cupped his face in your hands. Leaning in, you pressed your lips to his, admiring how soft his lips were.

The kiss quickly turned passionate, and Steve turned your body, pressing your back against the wall as his tongue slipped past your lips. It definitely wasn’t his first kiss, that’s for sure. Clothes were quickly shed and once you stepped back from each other, you both were completely bare. Steve’s cock was fully hard and twitched under your gaze. Cupping your own breasts, you smirked as he blushed.

“How about we use that sleeping bag?” you suggested, pointing to the rolled up bundle of fabric.

“That seems agreeable,” he repeated his earlier statement, making you giggle as he unwrapped the sleeping bag and unzipped it. Thankfully, it was a large sleeping bag and could easily fit the two of you. He slid in first and held open the flap for you

Slipping inside next to him, you pressed up against his warm body. “We can take this slow, if you want.”

“I do not believe I want to wait any longer,” he murmured, leaning forward and kissing you again before shifting so he was hovering over you, his knees between your thighs while his arms were braced on either side of your head.

“Well, alright then,” you shrugged, reaching between your bodies to stroke his cock. He was hard as steel and groaned softly as your fingers teased the tip of his cock. “I’m on the pill, so feel free to Twinkie instead of Toaster Strudel.” His perplexed look made you laugh, and you notched him at your entrance. “I’ll explain later.”

He accepted your answer to his unasked question and slowly pushed forward, pressing into your pussy with a slow yet constant pressure until he was fully seated. Capturing your lips again, he growled into your mouth as he pulled back and slammed forward, making you squeak.

“Fuck, Steve,” you moaned against his lips as he began to slam himself forward, filling you completely with each delicious thrust of his hips. The sleeping bag was slowly becoming unzipped the faster he thrusted, but you were so lost in the feeling of him inside you, you couldn’t manage to care.

“You’re so wet,” he commented through gritted teeth, looking down at where your bodies were connected. “Amazing.”

Arching your back when his cock brushed the sensitive part of your inner wall, he pressed closer against you, grinding his pelvic bone directly against your clit. You reached up, digging your fingernails into his shoulders as his thrusts turned more urgent.

“I can feel your gorgeous pussy squeezing me,” he leaned down and whispered into your ear. “Let go, beautiful.”

Feeling his warm breath against the shell of your ear sent chills down your spine and added that extra tingle of pleasure that sent you over the edge into your orgasm. Your fingers were squeezing the muscles of his arms in time with your pussy squeezing his cock, and you heard him take a sharp intake of air before the warmth of his cum filled your belly.

After his cock finished pulsing inside you, he collapsed on top of you, breathing heavily, and you ran a hand up and down his back. “Are you okay?”

“Yes,” he panted, “and I do believe I understand your earlier reference about those snacks.”

Chuckling softly, you whimpered when he scooted backward and pulled out, watching as he stared in awe at his cum leaking from your pussy. When he looked back up at you, you smiled softly and he blushed, reaching for his shirt and slipping it over his shoulders.

“Was that okay?” he asked nervously.

“That was more than okay,” you replied, nodding at him when he handed you your shirt. “I think we both deserved a break. But just remind me to erase the security tapes for the stockroom before we leave.”

Steve’s eyes went wide and he looked up, spotting the security camera pointed almost directly at the two of you. “Oh...”

“It’s okay,” you laughed, “don’t worry about it. We’re both consenting adults and we had some fun. I’m gonna go clean up. I’ll be right back, alright, Steve?”

He was quiet, fiddling with the hem of his shirt, and you were about to repeat yourself when he spoke first.

“Cas.”

You raised a brow. “What?”

“You can call me Cas.” He lifted his eyes to meet yours. “It’s… it’s a nickname. I prefer it over Steve.”

“Oh,” you smiled, “okay, Cas. I’ll be right back.” You stepped forward, then stopped, turning to face him again. “And the offer to sleep on my couch is still on the table, by the way.”

Cas nodded and smiled back at you, buttoning his shirt. “Thank you, Y/N.”

Winking at him, you slinked carefully back to the employee bathroom, avoiding any security cameras. While you offered for Cas to sleep on your couch, the idea of him sharing your bed seemed a lot more enticing.

Only time would tell.

"Oh," Cas said simply, nodding to himself. A moment later his confusion was back twofold as he frowned and glanced between Business Suit and Dean, inquiring, "What should I do?"

Dean opened his mouth to tell Cas that he already knew what to do when he realized that Cas didn't. He had very little experience with flirting.

Sure, Meg had flirted with him any time the two were in the same general vicinity but he highly doubted that counted. Cas had probably only seen her flirtatious remarks and sexual innuendos as taunts from a piece of demon hellspawn.

And besides that admittedly passionate kiss the two had shared, that Cas had already explained had only been due to him following the example set by the porn he had watched earlier, there had been no hint of any true romantic interest or chemistry between them.

Sure, there had been a few people who complimented Cas' undeniably good looks. But half the time their comments were made when Cas was nowhere in sight or earshot.

Besides, compliments weren't flirtations without intent.

And Dean highly doubted that fucking reaper had bothered to flirt with Cas before tricking him into sleeping with her. Just the thought made Dean's blood boil all over again.

So, no. Cas didn't have any experience with flirting, let alone how to respond to it.

Apparently, Dean took too long to advise Cas because the next thing he knew, Business Suit was curling a hand around Cas' wrist and explaining, "You should come over to the bar with me. Let me buy you another drink. See how things go."

A few seconds later, Cas and Business Suit were across the room, sitting down at the bar. Dean blinked, still trying to process what he had just witnessed, before turning to Sam and demanding, "What the hell just happened?"

"I...have no idea," Sam admitted, looking rather taken aback himself. Their waitress passed their table, making eyes at the younger of the two brothers again.

Like a loyal puppy, Sam was on his feet a second later to trail after her. He clapped Dean on the arm before disappearing after her, mumbling, "Lauren gets off work in five minutes. Don't wait up."

It took Dean another few minutes to realize that he had been stuck with the fucking check.

*     *     *     *      *     *

For the next fifteen minutes, Dean glared at Business Suit's back as he threw back another shot of whiskey. He had switched to the hard stuff after another beer.

He needed considering the shitshow that was his day. His replacement waitress, an engaged woman with short black hair and a name tag proclaiming her name to be Harmony, seemed understanding.

Cas and Business Suit seemed pretty chummy, sitting right beside each other at the bar, their arms pressed together. Business Suit was tossing back shots of cheap vodka while Cas had ordered another fancy cocktail.

It wasn't a Cadillac that time, instead the drink in his hand looked like an Old Fashioned. He kept fiddling with the twist of citrus rind floating in the dark liquid.

He seemed to be enjoying himself though Dean wasn't sure if that made him feel better or worse. Already there was that horrible feeling of jealousy burning him alive from the inside out.

It intensified every time he saw Cas smiling or laughing at something Business Suit said or did, like a stabbing pain in the chest. Every time Business Suit reached over to fuss with Cas' tie or brush an imaginary eyelash off his cheek.

It was driving Dean crazy, having to watch the angel he had been ass over ankles in love with for the past eight years getting schmoozed by some yuppie asshole. But he didn't know what else could do.

He couldn't march over there and break the two apart. Not without Cas questioning his motives and Dean having to come up with some sort of bullshit excuse that Cas would immediately see through.

He had considered faking an emergency but that would just make Cas worry. And Dean wasn't in the mood to get smited for lying to an angel.

He had also thought about just leaving and returning to their motel room. Cas had his wings again thanks to good old Chuck, he could find his way back.

Besides, with the way Business Suit was getting all touchy feely with Cas who didn't seem to mind all that much, the angel might not even return to the motel room that night. And didn't that make Dean want to throw up his lunch?

He was stuck between a rock and a hard place with nowhere to go. To think, he hadn't thought the hunt could get any worse.

He had just wanted to unwind with a few beers, maybe stop at some hole in the wall diner for a couple burgers, not watch some douchebag get all handsy with his angel.

Ugh, he needed another drink.

He waved Harmony down as she walked by his table, pointing emphatically at his glass of whiskey with a desperate pout. She nodded back at him with a friendly wink and an encouraging thumbs up before she disappeared into the crowd.

He turned his attention back to Business Suit who was in the middle of the old yawn truck, curling his arm around Cas' shoulders. Dean bristled.

Cas deserved better than that kind of cliche move. It was better suited for high school kids on first dates than angels who had saved the world a dozen times over.

Cas deserved genuinely romantic stuff like red roses and chocolate covered strawberries and bubble baths. Shit like that.

And yes, Dean realized that he was being a selfish idiot since he had never given Cas any of those things in the eight years they had known each other. But he wanted to. More than anything.

But that couldn't happen if Business Suit ended up charming his way into Cas' pants before Dean could.

He was in the middle of thinking about how much he would absolutely love to kick that prick's ass when Harmony returned, setting a glass down in front of him. He frowned at her, complaining, "Aww, c'mon. Water? Really?"

"Trust me," she informed him, crossing her arms over her chest while leveling him with a no nonsense look. "You need it, hon. Can't go confessing your undying love to Blue Eyes over there if you're drunk off your ass."

"How...?" Dean mumbled, narrowing his eyes at the waitress.

Harmony just shrugged and flashed her engagement ring at him, the large diamond glinting in the lights of the bar. Smiling to herself, she casually explained, "Me and my fiancee have had our fair share of rough patches. Hell, she thought she was straight when we first met. Keep your chin up, things will work out."

With that, she turned and walked away to take someone else's order, leaving Dean with his thoughts. Talk about irony. Or was it just a coincidence?

Whatever. Either way, Harmony's words struck a chord deep within him.

He nodded to himself as he raised his glass to his lips to take a long sip of ice cold water. Leaning back to get more comfortable, Dean just waited.

As it turned out, he didn't have to wait long. A few minutes later, Cas abruptly stood from the bar.

He turned on his heel and stalked back over to Dean's table, helping himself to the seat across from him and the glass of whiskey that still held a few sips of liquor. Dean waited patiently for some sort of explanation, glancing over at Business Suit who looked rather taken aback himself.

When Cas said nothing, even after he took the liberty of polishing off the whiskey, Dean took the initiative himself. "So... How'd that go?"

"I don't think I enjoy flirting," Cas relayed with a solemn nod. Tapping his fingers against the side of the whiskey glass, he amended, "Then again, I may not have done it correctly."

"Alright. Keep going," Dean instructed, gesturing for Cas to continue. "I'm all ears, man."

"Eric complimented me. Frequently. But it seemed rather insincere," Cas reported. "Our conversation switched topics to antiques. I told him about the bag of keys I selected at the last shop."

"Oh, yeah?" Dean hummed before taking another sip of water. "What'd he think about that?"

Cas hunched his shoulders, still fiddling with the empty glass. His voice was gruffer than usual as he explained, "He told me that I would be better off selling them for scrap metal. That they're useless trinkets and their only value is sentimental."

"I'm guessing you disagree," Dean observed. Cas just nodded.

"Admittedly, the keys do not hold much monetary value but I don't understand why that matters. That's not why I like them," Cas claimed, his brows knitting together. "They hold memories, secrets, of those who once owned them. They may have locked journals or jewelry boxes, guarded family documents or heirlooms. They still do. They're human. That's why I like them."

The explanation was so enthusiastic, so passionate. So much thought and care and attention put into the answer. It was so like Cas it nearly took Dean's breath away.

The next thing he knew, he was leaning across the table to press a quick, chaste kiss to Cas' lips. A dopey grin was stretched across his face when he sat back, Cas blinking at him, incredulous.

"Dean...?" The angel whispered, his words nearly inaudible. "Why did you do that?"

"Well, to be honest, Cas, I'm not really sure," Dean admitted a little breathlessly. Running his hand through his hair, he made sure to tack on, "But I do know it's long overdo."

"Oh," Cas murmured, his cheeks actually flushing with color. "Then I suppose this is as, too."

“Sure shoot, I mean… Ask away,” You corrected your choice of words to keep Cas from once more derailing the conversation by misunderstanding you. No matter how cute you found the angel when he pulled that confused puppy look now was definitely not the time.

Yet, though it seemed as if you agreeing to listen should have made the angel jump into action and tell you whatever it was that was on his mind, he stayed silent. From time to time he’d open his mouth, only to close it again with a frown and a head shake. Something was definitely up. Especially considering how weird the angel was acting. 

Castiel normally stood completely still, but there he was, fidgeting back and forth in front of you like a schoolboy caught doing something bad. As you caught him once more opening and closing his mouth without speaking before turning to look around the room you decided you had to be the one breaking the silence as he seemed incapable of letting you know what was going on.

“What’s wrong? Do you need me to call Dean and Sammy in?” The two questions left you in quick succession as a million others patiently waited their turn in your mind. If it was that hard for Cas to bring it up it had to be major. Like, end-of-the-world major. Maybe he needed your help with something possibly life threatening? Or maybe he had still not understood whom or what you’d be fighting properly. With the way he was acting it seemed like the world was actually about to end in just a few mere seconds.

“No! No… I just need to ask you. Not them,” Castiel’s eyes had widened at your questions, and  his voice was slightly higher than normal as he dismissed the need to bring the two other hunters into the fray. His blue eyes, the colour of the sky on a sunny day, were once more focused fully on you as he shook his head. Yet, the actual question in need of answering didn’t follow like you’d thought it would. Instead he just looked at you, swallowing audibly in a way that really made you fear for the worst. What could be so bad that the Winchester’s couldn’t join in? And why did he need you and only you?

Hell, you’d fantasized about the angel needing you more than once. But this… This wasn’t exactly  what you’d had in mind. If the wide-eyed look and fidgeting ways of the angel of the lord standing in front of you were anything to go by, it seemed like it might be your turn to sacrifice yourself for the greater good and meet your maker. Figuratively of course, since God had been nowhere to be found for decades, eons even.

“What is it Castiel? Unless you tell me I can’t answer or help you,” You bit back the urge to raise your voice out of frustration as you watched Cas struggle with whatever it was he needed to ask you. It was clearly hard for him to ask, though it really shouldn’t be. Firstly you were (secretly) in love with the feathery fool and secondly you would do whatever it took to help your friends, family and, by extension, the world. Still, by the way Cas took another two steps forward and seemed to steel himself you guessed some of your agitation still shone through though you’d try to keep it at bay. So much for that acting career…

“Ok… (Y/N) I need to.. Need to ask you something,” Castiel parroted his earlier words before taking a slightly shaky breath and focusing his eyes somewhere right above your head. “Were you… No wait,” Cas frowned as he turned slightly away from you, as if he was hiding something before, just as quickly, turning back.

“Was I what Cas?” Ok, now you were more confused than worried. The angel didn’t make any sense. Or, less sense than normal at least…

“Did you run through my mind? Because I am checking you out… No wait,” Castiel’s words left him fast and jumbled as the angel panicked in front of you. Your own thoughts, as you gaped at the awkward angel in front of you, were no less panicked as you tried to make sense of what was happening. “No,,  I mean, are you ice cream? Uh, no, You could never be ice cream, because… Wait, this makes no sense, you are human and…” Castiel continued to fumble adorably in front of you, looking increasingly awkward and panicked, his hands fidgeting and the normally direct and stoic angel going to great lengths to avoid looking directly at you.

Yeah… From your point of view it suspiciously looked like Cas was trying to flirt with you. But that was impossible. Not only was this the same guy who didn’t understand phrases like “what’s up”, but you’d always resigned yourself to being, at best, a friend and, at worst, an acquaintance that just happened to live with Dean and Sam that Cas just kinda tolerated. Yet, as Castiel continued speaking, his eyes going to his own shaking palm as if he was double checking something you realised that your suspicions were most likely correct.

“Are you an... No,” Cas sighed in frustration as he looked back down at his open palm, no longer turning to shield the gesture from your confused eyes. “Did you fall out of… No, sorry. I mean did it, uh, hurt when.. This isn’t going to work is it?” Damn it, he was too adorable.

“Cas, are you… Trying to pick me up?” You asked, finally finding your voice again as your maybe not so unrequited crush stood, shoulders slumped, in front of you. A personal summer storm of butterflies and rays of fucking sunshine causing havoc on your heart, stomach and mind as you desperately fought the urge to smile until you were 100% sure you weren’t just dreaming. Hell, you even stealthily pinched your own arm in confirmation. You’d been in love with the angel since the first time he showed up out of nowhere, literally descending from heaven and flipping your whole existence out of balance with his small smiles, and larger than life heart.

“What? No, I’m not lifting you at all (Y/N). I-I was trying to… Flirt,” Castiel seemed to stutter a little over the words as he hid the hand he had been constantly looking at behind his back and turned his eyes downward towards the ground. “Dean said that was how I should show my intentions. But I failed,” Seeing the angel’s shoulders slump further as he got that sad, confused puppy dog look squeezed at your heart with enough force to make you momentarily breathless as you looked at him.

“No, you didn’t fail. Well, you did. But, yeah…” Your own words were coming out as jumbled as those of the angel. If anyone had been watching they would’ve found it hard to believe that the two of you were a part of the group that had saved the whole human race from extinction time and time again. Not when neither of you could string a full sentence together without becoming a hot mess. “Cheesy pick up lines aren’t the best for flirting anyway Cas, it’s best to say what you mean. Like…. I-I… I mean, I like you,” This time it was your turn to carefully study the floor, ceiling and everything that wasn’t the angel in front of you.

“You do? But… I failed,” Castiel was an adorable mix of confused, hopeful and worried as he finally lifted his eyes, though you still kept yours low, looking instead at his shirt and tie combo, where it was peeking out underneath the oh-so familiar trench-coat. “Dean said…You like me? As in how I like you?”

“Yeah, I do Cas… I like you,” The words came easier the second time around as you  finally let the butterflies in your stomach free with a shy smile aimed towards the angel.

“So Dean’s flirting worked?” Cas looked confused, happy, but confused as he carefully took a step closer to where you were sitting, unable to get up since your legs had somehow turned to jelly and refused to work. “I thought… I thought I failed?”

“No, Dean’s flirting didn’t work.That stuff normally never works. What worked was you Cas. Your kindness, the way you care so much about all of this, all of us. Everything about you… That worked. Not Dean’s awful lines,” You said with a small laugh, finally properly meeting his eyes and seeing the pure wonderment that shone in them. “It would have been better if you just did it your way,” Though seeing him suffer through delivering those lines had been excruciatingly cute, but you'd never tell him that.

“So, if… If I tell you my…” Castiel cut himself off with a shake of his head and quickly dropped down to his knees so that his head was at the same height as yours on the couch. His azure eyes shone with determination and the earlier awkward fumbling was nowhere to be seen as he finally said the only words he had to say. His deep voice sending pleasurable vibrations up and down your spine. “I like you (Y/N), and I wish to start a relationship with you,”

This time you were the one left a bit tongue-tied. So, in lieu of words, you leaned in and placed a soft peck on your angel’s lips. Happy to see that that didn’t get lost in translation as Castiel broke out in a smile a thousand times more charming than any pick up line.

Surprisingly, Dean gets his wish as it turns out that Castiel is gay, and Dean is one of the only men who listed himself as gay or bisexual. So, after Jennifer, who is a single mom finally looking to date again after a rough divorce and is a knockout, gets up for the second date, Castiel is guided over by the librarian.

He sits gingerly and looks up at Dean. "Hello, I am Castiel Novak," he says in a beautiful deep voice then pauses. Dean opens his mouth to introduce himself, but Castiel starts talking again and just keeps going. "I am 32. I am in good health. My blood type is AB+. I do not smoke. I drink a glass of wine with dinner every night, but I do not overindulge. I have my latest test results which came back negative for any sexually transmitted infections right here. You can see them if you would like, and I would be willing to be tested again were we to become sexually active with one another.

"I live in town, and I work here at the library. I ride my bicycle to work, because I do not own a car. I live with my brother who owns the sweet shop on Main Street. I have one cat. I hope you aren't allergic. That was a problem in my previous relationship, though I am inclined to believe that he did not like my cat and just pretended to be allergic to him. I think that is everything unless there is something in particular you would like to know about me," Castiel finally finishes as he folds his arms on the small table and looks at Dean expectantly.

Dean wrestles with himself not to seize the perfect opening and ask what planet Castiel Novak is from. Dean isn't a cruel person, but sometimes it's hard to bite his tongue. When Dean doesn't respond immediately, Castiel squints at him and tilts his head to the side slightly. Now, Dean feels uncomfortable. 

"I wasn't expecting you to tell me your whole profile up front," Dean says as he tries to think of what information he could give the Castiel.

"I do that so you have the best knowledge with which to pick your dates," Castiel explains as though it is the most logical thing to do.

"You get to pick your dates too though," Dean says, and Cas looks at him as though that's a foreign concept to him.

"There are only two men here for me to meet. I don't get a choice. It's up to whether one of you chooses me," Cas explains, and Dean feels bad instantly for all his early judgments. Not in a pitying sort of way but in that he knows just how lonely and demeaning it must be to be Castiel tonight. While speed dating is already a sort of odd way to meet people, Cas has to put himself completely out there in order to hopefully catch one of two men's eyes, yet really have no say in the match himself. Dean would be skittish too if that's how his night was going to be.

"Well, Cas, I'm Dean. I work at the garage right down the street from your brother's shop. I'm 29, and I live alone, but my brother and his wife live down the street from me. I don't know my blood type, but I have it listed on a piece of paper in my wallet if you think it's important. I'm clean. I don't smoke, but I drink. I am allergic to cats, but I'm sure that's something we can get around. Let's see...I'm an Aquarius, I enjoy sunsets, long walks on the beach and frisky women and men. That last part was a joke," Dean clarifies when Cas starts squinting again.

"Switch everyone!" the librarian calls as the timer goes off.

"Oh," Castiel says in surprise that their time is up. Dean can see the slight frown that he gets as he looks over to the time stand. "I guess, I should move. Thank you for your time, Dean. I hope you have a pleasant evening," Castiel says as he stands to go. Dean doesn't want him to move. Cas may be the oddest person here, but Dean's certain he's the most honest and open, and he certainly isn't just trying to get in Dean's pants, even if he did bring his STD test results with him. Dean looks around the room at the multiple good looking women and men, and makes a decision he normally wouldn't.

"Or, we could get out of here and grab a cup of coffee. Maybe get to know less clinical details about each other," Dean suggests as he places his hand over one of Cas'. 

"But, what about your other dates?" Castiel asks with real concern.