I have a prompt for you: Cas/Dean and Sam/Gabriel, Cas and Dean both like each

other but don't know it. They both tell Sam who comes up with a clever way to

get the two together

I wasn't really that surprised, actually.
Yes, of course there was that first bit of shock that hit me when I found out. I mean, Dean really is quite the womanizer, and he sure likes his women. And Cas- well, he's a celestial being. But like they say, you can't really choose who you love. And even before I was formally told, I could tell that they had something special. The way they look at eachother- it's the way I used to look at Jessica. Stolen glances when they think the other one isn't looking, the way Cas's face lights up when Dean walks into the room. The way Dean's always worried if Cas is okay. Naturally, I was a bit fed up with all the hiding and pretending. So finally I decided to get them together.

It was a hot day in late spring. Dean and I were sitting on the hood of the impala after the sucessful hunt of a Wendigo. The noon sun was high in the sky and beating down on us with its vengeful glare, causing sweat droplets to collect at the base of my collarbone. Dean popped open the cooler, tossed me a beer, then took one for himself. The grass around us was faintly rustling, and we just sort of settled into a comfortable silence as we opened our beers and took simultanious swigs. After a little while, the heat became a little much for me, so I ditched my green jacket and rolled up the sleeves on my plaid shirt. Dean followed, going so far as to shed everything save for his v-neck t-shirt. After a few more seconds of comfortable silence, Dean finally spoke up.
"Hey Sam, do you ever think about if we're ever meant to be with someone?" I pondered this question for a little bit. "Well everytime I start thinking that, that person ends up killed, so not really. I think our lives are too complicated for that. Why do you ask?" I finished up the last of my drink and set the bottle down, letting the sunshine roll across my face. He stared into his bottle. "I don't know, sometimes I get the feeling that there's someone out there who it will finally work out with. I guess it's just a stupid thought." He ran his hand nervously through his hair, and I perked up. "Dean, is there something your not telling me?" I leaned forward. He whipped his head around. "What? No! I was just thinking out loud." I wasn't buying it. "Dean, come on, don't play that game with me. What's going on?" I probed. Dean sat silently for a few moments, toying with his beer bottle. Then he turned to face me. "I think I like Cas."
I raised my eyebrows slightly. "Yeah, we all like Cas," I played with him, getting him to go a little deeper. He rolled his eyes and hit me. "No, you idiot, I LIKE like Cas. Alright, I might be a little in love with Cas, okay?! You don't have to be a little shit about it," he grumbled the last part. "Are you..." he peeked back up at me. "Are you...weirded out?"
"Weirded out?" I threw my head back and laughed. "It was so obvious, Dean." Dean smiled a little, then his face turned serious again. "The only thing is..." he trailed off sadly. "There's no way he feels the same about me. I mean, he's a friggin' angel! And just 'cuz im..." he cringed at the word, " gay for him doesn't mean he is for me. Like I know he thinks of me as a super close friend, but no more than that." My heart softened for him. That's gotta be harsh. "Well, im sorry you feel that way, man," I frowned, then playfully slapped his arm. "Hey, cheer up. Lets go get some pie."

That night we stayed at a local motel called "El azul." Dean wanted to go out to celebrate but I wasn't really feeling it, so he took off by himself and I dropped onto the bed to watch a little bad TV. I was surfing the 10 channels they had when I heard a flutter of wings. I turned around and there was Castiel, sitting next to me, staring at the screen. I jumped so violently that I practically fell off the bed. "Goddammit Cas," I breathed heavily. He turned to face me. "Sorry Sam," he grumbled, looking a little out of sorts, pulling on the sleeve of his trenchcoat. I paused. "well, what are you doing here?" He looked up. "Oh! right. I need to talk to you." I waited. "Well? What is it? Is there war in heaven? Did lucifer pop back out of the pit? What?" Cas fiddled with his tie. "Not exactly, no. I need your advice on something a little more mundane." He took a deep breath. "I may be having some...human...feelings for your brother." I stared. "Like, what kind of feelings?" Cas blushed intensly. "Um," he mumbled, "Romantic...feelings?" I sat back and smiled. "Cas," I teased, "Do you have a crush on Dean?" He looked straight at me. "It would be helpful if you could not poke fun at me at this particular moment." I tried to surpress my grin. "What's the problem?"
"I don't think Dean likes me in that way."
Oh, I just wanted to roll around in the Irony.
"What makes you think that?"
Cas got a sad look on his face. "Dean has quite the way with women." I understood- he didn't need to say anything else. "It's gonna be okay, Cas-" but before I could even finish, he was gone. I knew it was gonna be near to impossible to get these two stubborn idiots to man up, so I decided to talk to the expert.

The dim neon sign on the candy shop flickered ominously as I rounded the back. I didn't want to do this in the hotel just in case Dean came back, and I decided that this would be an appropriate place. I closed my eyes and spoke. "Oh Gabriel, archangel on high, I pray to thee for thou to get thou feathery ass down here." Nothing. "I have a need that concerns the help of thou-"
"Oh would you stop it with the 'thou's?" I flung my eyes open and took in the sight of Gabriel leaning against the opposite wall of the alley. He winked at me. "You know you could just ask nicely for me. How's it goin', big boy?" I rolled my eyes, but inside my heart did a little flip in my chest when I saw him. I told myself that was just because he was an all powerful archangel. "I need your help with something." He started to smile but I cut him off before I could even start to imagine what he was thinking about. "It seems that our brothers have developed an interest in eachother." Gabriel looked a little confused. "An interest like..."
"Like they are romantically interested in eachother." Gabriel smiled. "Ah, I see. Great, so little bro has finally found 'the one'. What do you need me for? Not that I don't love seeing you and hearing about our siblings love lives." I smirked. "Get this. Both of them think that the other one doesn't feel the same about them. Do you see where i'm going?" A sly grin started to creep its way onto Gabriel's lips. He had some nice lips-Soft and full and-wait why was I thinking about that?! I shook my head a bit. "So yeah. I want to find a way to get those two knuckleheads to," I dramatically clutched my chest, "confess their love for eachother. Thought you'd be the perfect person to help. So what do you think?" Gabriel rubbed his hands together mischiveously. "Oh, I've got the perfect idea."

Gabriel zapped us to the small field where the matchmaking would take place. From there, I made a little call to Dean.
"Hello?"
"Hey Dean, It's Sam."
"Yeah...What's up?"
"Could we maybe meet up at this field? It's about a couple minutes from the hotel. It's not hard to miss."
"Okay, sure...what's this about?"
"Just want you to see something."
"Alright. See you in a few."
We waited behind a giant tree for about two minutes until we saw the impala draw close to our location. Then Gabriel made the magic happen. He projected an exact copy of Dean into the middle of the field, but this version was covered in blood and dirt. The Dean-doppleganger called out in a pained voice. "Cas! Castiel! Help!"
By this time the real Dean had gotten out fo the impala and was watching with a confused look from afar. In the middle of the field, Cas appeared. He took one look at fake-Dean and rushed towards him. "Dean." He called. "Dean!" Cas got to him just in time for fake-Dean to fall over. Cas caught him in his arms. Fake-Dean coughed and sputtered blood onto the grass. "Dean, what happened?!" Cas frantically tried to help his wounds, but there were too many. "I...an attack...the hellhound got me from behind. Cas, i'm scared." From our position behind the tree, we could make out tears on Castiel's face. "It's gonna be okay, Dean. Breathe. You'll be fine."
"I'm dying, Cas."
This whole time, real-Dean stood, dumbfounded, unmoving, by his car.
Fake-Dean's breathing became labored and increasingly slow. Castiel tried to use his angel magic on him, and became panicked when nothing worked. Finally he burried his head in fake-Dean's shoulder and sobbed. "Goodbye, Cas," Fake-Dean choked out. "Dean," Cas cried. "I-I love you."
Fake-Dean went limp. There was a bit of silence, then the doppleganger's body slowly vanished. Cas looked up, his tear streaked face struck with shock. He whipped his head around and spotted the real Dean, who happened to have a very surprised look on his face. Cas stood. "Dean," he straightened his coat and wiped his eyes. "What-how-I don't-" His eyes widened with realization. "That wasn't you, was it?" Dean shook his head. "Cas, did you...did you really mean what you said? That you...loved me?" Cas looked sheepishly at the ground. "Dean, I thought- I thought you were dying, I said some things-"
"But did you MEAN it?"
Cas looked up, with the sincerest emotion in his eyes, and simply said, "Yes."
Dean let out a shaky laugh, and let out a deep breath. "I think i might- I might feel the same way." Cas smiled the biggest smile that I had ever seen.
Gabriel stepped out from behind the tree first, clapping. "Oh god, finally. That was painful. Do you know how hard it is to get you two to confess your feeling?" Dean and Cas froze. Then Castiel simply walked over to Gabriel, put a hand on his shoulder, and punched him in the face.
"Ow! What was that for?" Gabriel rubbed his cheek remorsefully.
"Just never do that again. Ever." I stepped out, too, and i could tell that Dean and Cas were too consumed by happiness to even be mad at anything. Cas turned back around to smile at Dean, and walked over to him. Gabriel took the final step and flicked his fingers, sending Cas toppling forward onto Dean. They fell to the ground, lips locked, and it was if the world around them didn't exist. My heart swelled for them, but at the same time, it clenched with longing. They got to be happy. I wished for that with all my soul.
Gabriel looked over at me and saw my expression of sadness. "Oh, come here you idiot," he said, grabbing me by the lapels of my jacket and pulling me down to meet his mouth in an explosive kiss.