Playing Cupid

Dean's POV

"Y/n? It's Dean, I need you."

"Dean?" You heard the voice you've been longing to hear say just above a whisper. "What happened? Is Sam ok? Are-are you ok?" She asked with worry in her voice.

You felt your heart warm at her words and you could stop the small smile that formed on your lips. After everything you said to her, after that nasty fight and not seeing each other for quite a while now. She still cares.

"Yeah I'm fine...but it's Sam," you told her and it was met with a few moments of silence.

"I'm on my way, where are you?"

*********

Y/n's POV; few hours later

You got to the motel as fast as you could in the Camry. You wanted to know the details but something was telling you that you needed to get there right away. There was no ignoring this feeling now.

Walking to the room Dean told you he was staying in, you began to wonder how things would be with him now. Would it be awkward? Would the two of you act like nothing happened?

As soon as you walked into the room, you felt two strong arms grab you. You struggled against them until the oh so familiar scent of Dean. You've never been able to describe it, there were so many scents mixed in that it was just Dean.

You hugged him back tightly, as if he would disappear any second. Suddenly it's like all the emotions you've been suppressing came to the surface and your eyes filled with tears. He held you back just as tight but what finally made those tears fall was when he kissed your head.

"Hey Y/n," Dean said and you could practically hear the smile on his face.

"Hey Dean," you said voice making it obvious you were about in tears.

"Hey," he said soothingly, pulling away to find your tear stained face. "What's wrong?" he asked.

"Nothing, I'm fine," you sniffed. "Now uh tell me what's wrong with Samantha," you said awkwardness settling in.

He looked at you for a few seconds wondering if he should wait to tell you before deciding against it. Dean let go of your arms and stood a reasonable distance away running his hands through his dirty blond hair.

You couldn't help but miss his touch, it was like your body was aching for it.

"A few demons caught him, I know where they are but there's too many of them for me to go in alone and Bobby wouldn't answer his phone," Dean said without a trace of awkwardness that was practically suffocating you.

"Demons?" You said a bit intimidated.

"I know you've only been on one hunt so far but I know you can handle it," he told you confidently. "Besides, you're my last shot," he said with a shrug.

"Alright I guess I'm going on a demon hunt," you said determined to get Sam back.

**********

Sam's POV

Everything was black. After your eyes adjust to the lighting a bit, you could make out the outline of a table and a few other chairs.

You tried to get up to inspect the room only to find that your still tied to the chair. Struggling against the ropes, you hoped Dean would get help.

Suddenly, you heard yelling and things breaking coming from outside the room. Please let it be Dean with help, you hoped. While you did believe in your brother's abilities, you knew there were too many of them for Dean to take down on his own.

Then the door burst open and one of the demons who captured you in the first place stumbled in. She didn't look so good, she was covered in blood both her own and not. You anticipated Dean to walk in and untie you but you weren't so lucky.

Instead it was a man you've probably never seen before in your life. He had black hair, wore a suit with a trench coat and was quite shorter than you.

The mysterious man then bent down and touched the demons head. The demon's eyes and mouth lite up with an almost blinding white light which you had to look away from. You weren't sure but it looked as if he smote the demon.

When you looked back at the scene, the demon woman had dropped to the ground and the man was staring at you.

"Who are you?" You asked cautiously.

"I am Castiel, an angel of the Lord," he said in a deep voice. Man, you thought, puberty must've hit this guy hard.

"An angel?" You questioned.

While you and Dean have hunted and seen many supernatural things, you've never encountered an angel before.

"Yes, now the demons are gone, Y/n is in town already so we don't have much time," Castiel said looking around as if someone would come in any second.

"How do you know Y/n? Why is she in town? And why is that a bad thing?" You fired off questions.

"I'll answer all of your questions in time but you have to let me explain," he said neutrally.

"Ok then explain away, but maybe you could untie me first," you suggested.

"No I cannot do that," he informed you.

"What? Why not?" You asked suspiciously.

"Because it won't work if you are untied, now listen," the angel ordered starting to get a bit impatient.

"I know Y/n and Dean care about each other deeply and that they are both very stubborn Humans who wouldn't reach out to the other without the need to. I set up for Robert Singer to be busy and you to be captured so Dean would call Y/n," Castiel began.

"So you want to play Cupid," you concluded with a nod to which the angel just looked confused. "Why do you care?" You asked.

"Because her mother asked me to watch over her after she died, so I have. I'm not her guardian angel though, I just check in on her when Heaven allows," Castiel explained. "I care because I want Y/n to be happy and Dean is what will make her happy," he finished matter-of-factly.

"Alright, what do you want me to do now?" You asked intrigued.

"I want you to pretend that the demons are still alive and are holding you hostage then once Dean and Y/n rescue you, I want you to help them fall in love with each other," he informed you.

"Ok, I'm in," you decided.