Having exhausted all other avenues of his research Castiel decided it was time to do the unthinkable. He'd have to ask Dean.
It wasn't that he didn't believe the hunter would be able to help him. He knew the eldest Winchester was actually known for the ease with which he could earn the affections of others. Castiel was more worried about Dean gaining the knowledge of what the angel was trying to do. The hunter was well known for being overprotective of his little brother at the best of times, and he didn't want to know what Dean would think of his feelings. Castiel would have to get the information out of the hunter without letting him know what the information was for.
The hardest part of all of his plans so far had been separating the brothers so he'd be able to talk to one of them without the knowledge of the other. He'd never really noticed before this adventure how much of their time was spent together. Nearly the only times he'd been able to speak to Sam alone had been if Dean had left for the night. He didn't really know how to get Dean alone.
Opportunity presented itself when the Winchesters were working out their grocery shopping lists. It was fairly clear that the brothers hated doing mundane things like that. They worked on a list for a few days before they would leave, making sure that nothing would be forgotten and they could get in and out quickly.
Normally the boys would do a chore like this together, but one word from Castiel about needing to speak to Dean and Sam was reluctantly offering to do the shopping alone.
As soon as the door was closed behind his brother, Dean's face split into a smile.
"Thanks, buddy! I hate grocery shopping."
The angel frowned. "I truly did wish to speak with you." He informed him, worried that Dean was going to try to slip away.
"Oh, I know. It's cool, we'll talk. I'm just so greatful to get out of doing that!" The hunter chuckled and clapped a hand to Castiel's shoulder, steering him in the direction of the library.
Once they were seated Dean prompted him to get on with it.
"So, what's on your mind?"
The hunter's face looked friendly, and curious. There was nothing to indicate that this conversation wouldn't turn out well. It didn't matter. The angel could feel his stomach turn in knots as he tried to think of what to say.
"Ever since I was human…" Castiel trailed off, not really knowing how to explain the emotions he'd been plagued with. He tried again. "When I was a human, I had to experience things I never had to before. Most pointedly, human emotions. There were so many, and they came all at once. I didn't know how to handle them, so I tried to just push them aside, and ignore them. It worked fairly well, and by the time my grace was returned I had a decent handle on them, or so I had thought. I believed that the return of my grace would be able to save me from my feelings."
Dean was beginning to look concerned, which was actually an expected reaction. The hunter hated talking about his feelings and was probably wondering why Castiel would have come to him with this. "Okay…?"
"Most of the more… overwhelming feelings have faded, but there is one feeling I have yet to rid myself of. I have been trying to ignore the feeling, but it won't go away. I was hoping that you might be able to help me figure this out."
The hunter's eyes widened and he looked almost spooked. "Uh… what kind of feelings are you having?"
"I feel an… attraction, and no matter what I do, or how I try to ignore it, it will not go away. I have given in, and I would like you to tell me how to go about revealing my feelings to the object of my affections."
Dean let out an explosive rush of breath that ended on a chuckle.
"Oh thank God! I was starting to get really worried there for a minute. I had no idea where you were going with this, and I thought I was going to have to pretend like I knew how to deal with human emotions. This feeling I know how to deal with." The hunter actually seemed pleased to be able to share his knowledge with the angel.
"So you've got yourself a crush, huh?" Dean grinned at Castiel in a way that made him feel he was being made fun of.
"I suppose." The angel tried to remember how to define a crush from his research. He believed it was comparable to infatuation. That would work. "Yes. I have a crush ."
The hunter chuckled, but probably only at the way he had accidently stressed that last word so oddly, though. "So you need me to tell you how to pick up women?"
Castiel paused before answering. He would like to correct the hunter. He wanted to make it clear that the person he was trying to 'pick up' was male, in case that mattered, but he was aware that the less Dean knew, the better. So, instead he nodded his agreement.
"Well, what kind of girl are we dealing with here? Different girls will need different approaches."
Castiel nodded his agreement again. That made sense. Certainly someone that was trying to get his attention would have to do it differently than if they were trying to get Dean's attention.
"So, what's she like?" Dean looked very interested in finding out what kind of girl had caught his attention.
Castiel had to take a moment before answering that question. How could he even describe the object of his affections?
"Well, is she good looking? Are all the other angels trying to get their hands on her too?"
The angel had to contain his reaction to that question. Yes, there were plenty of angels interested in Sam, but for very different reasons.
"Yes." He answered plainly, not bothering to elaborate.
"Well, that will make it a little more difficult. It's always harder when there are other dudes trying to get in your way." Dean seemed to contemplate the next question for a while before he spoke again.
"What kinds of things does she like to do? Maybe we can find something in common that will give you an in."
Castiel had, of course, already tried this tactic. He needed to at least try to give Dean something to work with, though. He had to force the pronoun out, and hoped that the hunter didn't notice.
"She likes to read."
Dean's face scrunched up dramatically. "Oh, no. She's smart?"
Not really knowing what that might have to do with anything, Castiel just confirmed the hunter's suspicions. "Yes. Is that a problem?"
"Well, no. Not really. It's just… the smart ones that are also pretty tend to be the hardest ones to get. They spend too much time trying to get people to realize that they are more than just a pretty face. It seems to make them kind of bitter about getting asked out." Dean leaned back in his chair, head falling back so he could stare at the ceiling. "This will certainly be a challenge."
Castiel hadn't really considered that Sam's intelligence would work against his plans.
"You should probably try to figure out what she's interested in. It'll be easier to make her feel like you respect her intelligence if you can talk to her about it. It's going to take time too. You couldn't have picked an easy one." Dean shook his head as if his picking one that wasn't easy was a bad choice, but thinking of all of his failed attempts to capture Sam's attention had the angel immediately agreeing to that assessment. It would certainly not be easy.
It was a week later before Castiel tried to speak to Dean about his feelings again. The first bit of advice had worked out quite well. Every time Sam figured out something that no one else had been able to, the angel had been there to make sure the hunter knew how much his intelligence was valued. At first, Sam had seemed surprised by the extra effort, but by the third time he'd done it Sam had actually blushed at the attention, with a quiet "Thanks, Cas" and a shy smile that melted the heart of the angel.
Clearly Dean's advice was leading him in the right direction, so he decided it was time to move to the next step.
"I believe I have convinced her that I respect her intelligence. What shall I do now?"
Dean's head popped up from the laptop he'd been staring intently at, and he glanced around the room as if the angel might have been talking to someone else.
"Dude. I told you. You've got to start conversations better. You can't just plop down and start talking."
Castiel considered Dean for a moment. "So, get this…" He said, causing the hunter to crack a smile.
"See! That's all I need." The hunter nodded, closing his laptop to give the angel his full attention.
"I have completed the first step. I need to know what to do next."
Dean's eyebrows shot to his hairline. "What makes you think the first step is completed?"
Castiel sighed and told him of his observations, carefully making sure to use the correct pronoun.
"She blushed? That's awesome! Nice work. Wow, you move pretty quick!" Dean seemed pretty impressed. It took a moment for the expression to fade. "I guess you've been going to see her while we're sleeping?"
A cold feeling of dread swept through the angel's vessel at the words. Of course Dean would have noticed that he hadn't left the bunker in days. Castiel hadn't thought about that. He quickly nodded in agreement with the explanation Dean had already come up with for him. He didn't enjoy lying to the Winchesters, but he was not ready for Dean to know what he was doing yet.
"I guess the next thing I would do is bring her gifts. And I'm not talking flowers and chocolate like they do in the movies." The hunter rolled his eyes as he said it, clearly indicating that he thought those gifts were foolish. "You want to ease her into the idea, so you don't want to do anything too revealing. If she likes reading, maybe you can let her borrow a book you know she'd be interested in. Even if you have to go buy the book before you can let her borrow it."
Dean paused as if waiting for confirmation that Castiel understood what he was insinuating. The angel nodded along. It was one of those things that humans called a 'white lie'. A harmless half-truth that they seemed to think was acceptable.
"Make sure you find other ways to compliment her. Now that she knows that you are interested in her mind first, she'll be much more likely to accept other compliments too."
This was one of the other things Castiel had read in his research. Complimenting people was supposed to be a way into their heart. He had decided it was one of the suggestions that had no real merit, but now that Dean was also saying it he'd have to rethink that.
"Don't go crazy with the compliments. You have to be a bit subtle about it still. Just tell her that her hair looks nice today, or that her shirt brings out the color of her eyes, or something. Don't go writing sonnets about her or anything." The hunter gave Castiel a look that said he was very serious about that part.
"I don't believe I am creative enough to do something like that anyway." The angel reassured his friend. "Thank you, Dean."
Castiel received a nod and a smile in response before he was ignored again in favor of whatever Dean was doing on his laptop.
In the following two weeks Castiel worked on using Dean's advice to get closer to Sam. He had taken to making sure that the hunter's coffee cup was always full. He'd studied the hunters as they set the machine to make their coffee, and had even begun making another pot when it was low. He'd then pour another warmer cup and exchange it for the one Sam had been drinking. The hunter had begun gracing him with a grateful smile when he would reach forward to take a sip of cold coffee and found it to be warm and satisfying instead.
It wasn't long before Dean started looking suspicious of his actions. Before the elder hunter could become too dubious Castiel decided to start bringing the pot of coffee with him to refill Dean's cup as well. It seemed to quell his mistrust.
The angel tried to think of other gifts to give Sam that wouldn't cause too much fuss, and his next stroke of genius had been vegetables. He knew the hunter had a hard time finding fresh vegetables at the local grocery, and tended to make an unhappy face as he looked at his choices. Although the plan to make Sam comfort food had fallen through, he realized he could still get the hunter some foods that might make him happy.
Castiel searched for a nearby farm, and struck a deal with the owner. He would make some much needed rain for the area, if the farmer would provide him with a variety of fresh vegetables. Of course the man agreed, although he clearly didn't believe that Castiel was truly an angel.
A wet half hour storm over a small section of Kansas later and the angel was laden down with multiple pieces of each of the vegetables that the farmer grew. He graciously accepted his gifts and thanked the farmer even as the man begged forgiveness for his disbelief.
When Castiel returned to the bunker with his overflowing boxes, he tried to make it seem perfectly normal for an angel to show up with vegetables for his charges. Sam was overjoyed when he saw the variety and quality of the produce, although Dean was beginning to look suspicious again. Castiel tried to pretend that he didn't notice. He didn't know how to explain his actions without giving himself away completely.
He had even found ways to complement Sam without being too obvious. He was actually fairly proud of the ways he'd come up with to tell the hunter how attractive he was without saying it outright. Knowing he was pushing his luck already with Dean, he always made sure the elder hunter was outside of hearing range before he showered attention on the object of his affections.
There was one question Castiel wanted to ask, that he was honestly a little afraid to. He knew that Dean wasn't big on talking about his feelings, and he was already lucky that the hunter had been as helpful as he was so far. By the time he had an opportunity to talk to Dean again, he'd worked up the courage to go ahead and ask it.
"How do you know if you are in love?"
Dean looked startled by the question, but his surprise quickly faded into that wary expression that he'd taken to wearing.
"I don't know, buddy. What did the internet say?"
"An intense feeling of affection for someone. A deep romantic or sexual attachment to someone." The angel answered immediately.
"Those are literal definitions. Did you read anything else about it?"
"The ways that people said they knew they were in love were very strange. Like they missed the person when they were not around. I feel as though there are multiple people that I could say that about. Some said that they couldn't eat or sleep when things were not going well with the one they loved. I never eat nor do I sleep, so I wouldn't be able to use that to tell."
The hunter's eyes held a deeper suspicion at that. He stared intently for a moment before seemingly ignoring the angel's questions completely.
"Do you think you're ready for the next step?" Apparently Dean didn't want to talk about love. Castiel allowed the subject change, although he still had questions on the subject and he really didn't have anyone else to ask about it.
"Yes. I believe that my gifts have been well received. What should I do now?"
"You're going to have to gather your courage for this one, buddy. Now that's you've got her all buttered up it's time to pop the question." The hunter's gaze was shrewd and the angel feared that he was being led astray at this point. It was very hard to understand the hunter's sense of humor at times.
"What question?"
"Well, it's time for you to ask her out! You've gotten close to her, so now all that's left is finding out if she's interested. You don't want to put a lot of time and effort into someone that's not interested at all." Dean's expression had faded back into that knowledgeable look he'd been using the other times they had talked on the subject, which eased the angel's hesitation.
"What should I ask?"
"I'd usually tell you to ask her to dinner, but you don't eat. Maybe see if she'd like to see a movie. Have you ever been bowling? Maybe you could do that." The hunter seemed genuinely interested in helping him find somewhere to take his date.
"I've never been bowling before. It doesn't seem very difficult though."
"Well, girls don't really like it when you beat them really badly at something anyway, so maybe you could give that a shot. Just make sure she knows that you've never played before. You don't want her to lose all respect for you if she beats you really bad."
It had been nearly a week of trying to get Sam alone before Castiel had finally had a chance, although Dean was only in his room and was very likely to come out at some point during the conversation. The angel only hoped that it wasn't until he had his answer.
"Sam, I've been wondering… would you like to go somewhere with me?"
The hunter's head popped up from the book he'd been absorbing. He looked intrigued by the question.
"Where did you want to go?"
Luckily Dean had given him some ideas about this.
"I would like to go bowling. I've never been bowling before."
Unluckily, Dean chose that exact moment to walk into the library. He paused just inside the door, glancing between them both. It took only a moment for him to realize the reality of the situation.
"You're hitting on Sam? Dude! I knew it!" Dean was huffing a bit dramatically and waving a hand to indicate the angel. "I wasn't really convinced until those damn vegetables, but I freaking knew it. I can't believe you got me to help you. I thought you were talking about doing a little cloud seeding, not hitting on my brother!" Dean glared at him, making it quite clear how unhappy he was to find out his advice had been used to get to Sam.
"You're hitting on me?" The youngest Winchester was clearly surprised by this new information. He also seemed unconvinced that was what was actually happening. Castiel had a hard time meeting his eyes..
"Yes…" The angel trailed off, not knowing how else to answer.
"Oh my God! This is what all this has been about this whole time?" Dean seemed to be pretty upset by the revelation. "Those searches on my laptop about physical attraction? You've got the hots for Sammy?" The hunter's voice had raised in a combination of panic and disbelief.
Castiel refused to answer, glaring hard at the floor and trying to pretend he was anywhere else. There was a long moment of silence as it became clear that the angel had no desire to reply.
"Is this what all your talk of emotions has been about?" The hunter's tone settled into a kind of forced calm.
Castiel couldn't think of a reason not to answer that question, so he did. "Yes."
"And what did you learn?"
The angel tried to think of a way out. He hadn't really expected to have to discuss his feelings today. It seemed he had already messed things up so badly that it was probably useless to keep trying to avoid the conversation. "It's hard to say, as I have never experienced these feelings before."
The look on Dean's face said he was not satisfied with that answer. When Castiel looked to Sam to see his reaction, the other hunter only continued to look surprised and confused.
"I do feel… a physical attraction." The angel could feel his face heating at the admission. He was also aware that it would only get worse.
"So, you decided to seduce him?" Dean seemed angry in that protective way he got when he was talking about his brother. Sam was clearly becoming more uncomfortable with the way the conversation was going. At least he was glaring at his brother and not Castiel. The angel probably would not have been able to answer with the younger Winchester's eyes on him.
"I don't posses the skills necessary to do such a thing."
That comment seemed to throw off Dean's argument, and his brows drew together in confusion. "So, what exactly was your endgame here?"
"What do you mean?"
"What were you hoping to get out of this if you didn't think you'd be able to seduce him?" Even though Dean still seemed a bit confused, he asked it in such an accusatory way it set the angel on edge.
"I don't know!" Even Castiel was surprised by his own emotional outburst. "I don't have any idea what I am doing! I've never experienced these feelings before. I have no idea what I'm meant to do with them." The angel tried to calm the emotions coursing through his veins. Before he could, Sam asked a question.
"But why me?" The hunter's voice was soft and curious, but Castiel still had too many uncontrolled emotions and he reacted without thinking.
"This is not my fault! You're a work of art! And you are never wearing a shirt! You did this to me!" His tone was unnecessarily accusatory and he regretted it immediately.
Sam was clearly startled by the outburst, but had the good grace to look ashamed. "I'm sorry, Cas. I didn't realize I was making you uncomfortable."
"You weren't making me uncomfortable." The angel comforted automatically, before he felt a heat rush to his cheeks. "I mean, yes. I suppose... I was a bit uncomfortable." He didn't bother to mention that the discomfort he'd gotten from seeing Sam shirtless had mostly been within his own pants. The sentiment seemed to come across anyway as the younger brother blushed and the elder made gagging noises.
There was a brief silence as they all seemed to gather themselves, then Dean started on him again. This time he seemed a bit resigned, though.
"Seriously, man. You have to know that it would be much easier if you went after someone else. It seems like with the amount of time you have hung out with us you should've caught on by now that you don't sleep with the people you're close to. Why didn't you just tell us so we could take you to a bar? It might be a little weird helping you pick up dudes, but we would have done it." Dean actually sounded sincere, which warmed the angel's heart. He knew that the hunter would be incredibly uncomfortable with something like that, and the thought that Dean would help him out anyway was a very nice one.
"I do understand, and I do appreciate the offer." Castiel took a deep breath and steeled himself. "But I don't want anyone else." He was well aware that the statement was very revealing, and he knew it wouldn't be lost on either of the hunters.
He watched as the comment sunk in. Both hunter's eyes widened, and when Sam leaned forward to rest his arms on the table he managed to knock his empty mug to the floor with a loud clank. Neither of them took their eyes off the angel, though. The silence that filled the room was deafening.
"Me?" Sam asked in what could only be described as disbelief.
"Yes." Castiel answered plainly. There was no point in hiding anymore. They already knew the truth; they were only having a hard time absorbing it.
"I don't understand." Sam had barely spoken during the conversation, and the angel was glad he was finally participating. It was a conversation he'd planned to have with only the younger Winchester to begin with. Although having Dean present had been mostly unavoidable.
The younger hunter continued, "Dean told me that you started experiencing emotions after you lost your grace. I get that you're still having a hard time controlling them... but he's the one that you share a more profound bond with. Why me?"
"I find that I would like to share more than just a profound bond with you."
The snort that issued from the eldest hunter at his words caused Sam's attention to swing his direction. Sam glared at his brother while Dean made hand gestures that Castiel didn't understand.
"Shut up, Dean." The younger hunter rolled his eyes as he turned his attention back to the angel. Dean hadn't said anything, but Castiel understood that the Winchesters seemed to have their own language sometimes, so he ignored it.
"Wait, wait, wait." Something seemed to occur to Dean at that moment and he paused his motions. "That's what those love questions were about? You think you're in love with Sam?"
Castiel averted his gaze before he answered. "I can't be sure as I've never felt that emotion before. I can only go on what I have learned."
There was a pause before Dean seemed to lose patience. "And?"
The feelings overwhelming the angel as he spoke were a mixture of fear and hope and some other less definable emotions. The fear nearly kept him from answering, but he had always been a soldier and he felt it was too late to back down now. He forced his eyes to meet Sam's. "Yes." His voice came out barely audible, but it carried in the quiet anyway.
The silence stretched for a minute until Dean finally broke it by moving. A happy smile split the hunter's face, and he clapped a hand on the angel's shoulder as he passed him, heading back toward the hallway. "Well, Sammy's been in love with you for ages, so I guess it'll all work out."
Castiel couldn't help the shock that crossed his face, and he turned his attention back to Sam. The hunter's face may have looked even more shocked than his own, and he stared at the doorway his brother had just exited through.
It took Sam a while to compose himself again, and by the time the hunter turned his attention back to him, the angel had been able to collect himself as well. He knew not to put much stock into some of the things Dean said. The elder hunter liked to make jokes.
"Listen, Cas..."
"It's fine. I don't expect you to return my feelings, Sam. I understand if that is not something that you are willing to do. My vessel is male, and I know that it can be hard for humans to accept the idea of a mate of the same sex. I had hoped that you would at least allow me the chance to try to earn your affections."
Sam huffed a laugh at that and finally met his eyes. "And then what? Hope the gay rubs off?" Even as his words were unsettling, his tone was kind. As it usually was.
"We don't have to have a physical relationship. I am perfectly capable of keeping my hands to myself, as they say. I only hoped that I could become closer to you."
The hunter rose from his seat and slowly made his way around the table between them.
"Are you sure about that? Isn't it my fault that you are stuck with all these emotions in the first place?" Sam was suddenly right in front of the angel, but before Castiel could react, the hunter leaned back slightly to prop himself against the table.
Castiel blushed, from his nearness and his words. "I didn't actually mean that." He admitted.
The hunter's smile was fond as he accepted the half-apology. "I know." Sam rubbed his palms across the front of his jeans in a gesture of nerves that even the angel recognized.
"So, how did you want to go about 'trying to earn my affections'?"
"Perhaps we can start with a date? Dean said that is what normal people do when they are interested in someone." Castiel said cautiously.
Sam huffed another laugh at that. "Okay. I think we can start with a date. But after this, no more plays from Dean's book of getting laid. I don't even want to know what he thinks step number two is."
"Alright." The angel agreed immediately, and was surprised by the happiness that shot through him at the idea.
"Besides, if that last comment he made was any indication, he's not upset that you were trying to hit on me. He was upset that he was unknowingly giving you advice on how to do it. It's probably a good idea to keep him out of it." The hunter sent him that boyish grin that made the angel's heart beat faster and he reached out toward Castiel's hand.
"That's good." He said, trying not to show how much the other man was affecting him. Although he brought his own hand forward to meet the other.
The calluses on the hunter's fingers rubbed pleasantly against his skin as their hands slotted together. Sam's was larger than his vessel's, almost dwarfing it. It was a sight that appealed to the angel in a way he couldn't define. When the hunter's thumb wrapped around to rub gentle in circles on the back of his hand a shot of pleasure rolled down his spine, unexpectedly.
"Cas." The angel realized his eyes were fixed on where Sam's hand was gently caressing his own and they snapped up to meet the hunter's.
"I'm just going to come right out and say this, because I know that subtlety goes right over your head."
Castiel nodded, he knew that it was true.
"You're not going to have to work very hard to earn my affections, because you already have them. I suppose I haven't been very good at hiding it if Dean already knew." The angel was graced with another shy smile, and his heart seemed to stop in his chest this time. It started again at a very quickened pace as the hunter's eyes seemed to sweep the entirety of his vessel. Sam's smile turned impish. " And I seriously doubt that physical compatibility will be a problem."