Author's Note: Collaboration with DeanCaslover1214

DISCLAIMER: I DO NOT OWN SUPERNATURAL OR TAYLOR SWIFT'S SONG "TEARDROPS ON MY GUITAR"

My original story included the song lyrics but had to be altered due to website regulation standards. However I'm pretty happy with this version.

Hope you like it!

Castiel Novak was very nervous, and nauseous. It was to be expected, he was performing a Taylor Swift song, teardrops on my guitar, in front of the whole school, including the man he loved, Dean. Cas started pacing back and forth behind the stage waiting with trepidation. Cas and Dean were best friends but if Cas had to see Dean hook up with another girl, he just might kill himself. Cas had loved Dean for years, ever since they met in the playground in kindergarten.

Charlie stood to the side, looking a little guilty. Well she should, a voice in his head thought, she was the reason he was doing this stupid thing in the first place.

Charlie was feed up of the UST, unresolved sexual tension, he and Dean were throwing off and signed him up for the Valentines Day talent show, and to sing the only Taylor Swift song that he liked, Teardrops on my Guitar. When Cas found out he was furious, but then he thought about it. If Cas had to live with Dean as his best friend for the rest of his life, that would have been fine. But Cas could not live with Dean as his best friend who hooks up with a different woman each week and eventually get married, completely unaware of Castiel's feelings for him. Cas loved Dean with all of his heart and soul, and could not stand to see Dean with a woman without knowing Cas's true feelings for him. And a small bit of Cas hoped that Charlie was right, and that Dean did feel the same way as him, and could love him. It was a small hope, one that he truly did not believe.

His thoughts of the young teen almost overwhelmed him. It completely silenced the world around him, engulfing him in a bubble of warm happiness. He jolted when the cold yet comforting hand of the principal pulled him out of his thoughts and gave him the five minute reminder. He started shaking, which Charlie must have picked up on because she immediately came to his side for a quick pep talk, Charlie style.

"Cas, calm the Hell down. Dean loves you, even though you don't think so. And you obviously love him, since you're this nervous. Just take a few deep breaths and do those actor warm up things."

"Actor warm up things?" He looked perplexed.

"Yeah, you know…" She started making awkward movements and noises that made him feel a little uncomfortable.

"You can stop, you can stop, I think I get the point."

"Great. Good luck, keep doing...that. I'm going to go sit next to Jo. Your singing better be romantic, its Valentine's Day so half the audience is hoping to get lucky tonight." She gave him a swift pat on the back and she was gone.

The lights began to dim in the audience and shift towards the stage as the booming voice of Principal Michael Milton dragged him out of his dreamy void once again. Okay, he thought, this is happening. I'm going on stage. I'm going to sing a song. He chuckled under his breath, I wonder if Dean's heart beats faster when he's the center of attention. No, he loves it.

"And now, without further adieu, Castiel Novak!" Principal Milton thundered.

The curtains opened, he was on stage. He sat down on the lonely chair in the middle of the stage with his guitar and little microphone. He scanned the crowd for a warm, familiar face, and the one in the middle of the front row horrified him.

It was Dean Winchester. Crap.

Wonderful. Now Cas had to deal with his crush in the front seat, while he sang a love song about Dean, while he replaced 'Drew' with 'Dean'. Fan-fucking-tastic. He tried to ignore Dean's unsettling presence as he started to play the familiar tune…

Throughout the song, thoughts buzzed in his mind like bees around a forbidden flower, keeping him in raw emotion for the entire performance. "Ignore the fact that Lisa is becoming his high school sweetheart, just look at Charlie, just look at Charlie…I wonder if he knows how much he breaks my heart being with random chicks that don't deserve him...I wonder if Lisa even knows how lucky she is to have him…Dean might not think he's perfect but he's perfect to me…I really, really hope she knows how lucky she is that he loves her instead of me… I love him with all my heart… Near the end of the song he shed a tear thinking about all the dreams he has had about them being happy together, forever. Once the song was over, he didn't even wait to see if he got applause, he didn't care. He faked a smile and ran off stage so he wouldn't have to face Dean.

Cas kept running until he got outside behind the school and hid behind the closet structure he could find which happened to be the dumpster. He fell against the wall and slowly slid down. Tear running down his face thinking about how he lost his best friend. "Dean is going to hate me forever and it's all my fault. How could I have been so stupid to think I could do this, let alone get him to love me. He deserves someone so much better than me. I love him, but he will never love me as more than a friend especially after what I just did. Why did his dad have to raise him to think that he could never be anything more than his little soldier." He was so full of anger ,fear and pain that the emotions was piling onto years of deep seeded hate for Deans father John. He loses control and continues to rant. "The horrible way that John raised Dean, Dean thinks for no one but Sam. Dean never thinks about himself, never goes after what he truly wants, because he thinks that he doesn't deserve it even when he does. I love Dean and I wish that Dean could even think about loving me back and think about himself for once in his life. To be honest I wish he could be happy even if it wasn't with me. Dean deserves some happiness in his life besides Sam. He is better than the life he was given."

He heard a thud, and fell into silence but couldn't stop the tears streaming down his face thinking about the life he knew he could give Dean if Dean would give him a chance. He sat in silence thinking for what felt like forever, but in reality was five minutes.

He heard another thud, this one was more of a bang. The rusted metal doors of the school burst open and out came Lisa, screaming with rage. Dean followed closely behind. Cas panicked and pushed himself further behind the cafeteria dumpster, and listened to the drama unfolding in front of him.

"What the Hell do you mean you're breaking up with me?!" Lisa screamed.

"Lisa, I-" Dean tried to explain himself, but he wasn't given much of a chance before Lisa dove back in, cutting him off.

"No, you fucking listen to me, Winchester. I have given you everything. I went to your stupid ass shoot-em-up movies, I took rides in that shitty car of yours, I even tried to make friends with your weird moose of a brother. And now you're saying that's all for nothing?"

Cas could see it in Dean's face that that line really hit him, he loves that car more than himself, and no one, repeat, no one, insults Sammy.

Dean's face turned from caring to a stone cold rock.

"Listen here, you bitch. We weren't even dating, we were fucking. Okay? You have no right to say you cared about my life. You know nothing about me. So yeah, I'm dumping you out like last week's apple pie because you never cared and you never will and I might deserve pain in this world, I know that I deserve to go to Hell, but I don't deserve to have to put up with you anymore."

Cas could tell that Dean has wanted to say that for a long time.

"So that's it? You're leaving me for your socially awkward maniac of a friend who acts like a fallen angel all the time?"

Dean smirked.

"Yeah, because my socially awkward maniac of a friend gives two damns what happens to me and I have had a crush on him ever since I looked into his big baby blue eyes in kindergarten but I never had to balls to say anything and tonight I found out he actually loves me. So I think I'm going to spend less time with sluts like you and more time, in fact, the rest of my life, with someone who means something."

Oh my god. He's talking about me. Cas thought, completely in shock.

He started to walk away towards the building.

"You asshole!" Lisa shouted after him.

He said nothing, he didn't even turn around, just shot his middle finger straight in the air at her. Castiel quickly realized that despite the wonderful turn of events that he just witnessed the worst was yet to come; Dean was heading to the dumpster. Crap….