I'm the Angel on His Shoulder

We were in Ohio investigating suspicious activity, and as we were finding out information, Dean was flirting with a bartender. She must be what is attractive to men, as I saw other men being attracted to her, but Dean flirting annoyed me a lot. Sam could sense it and I saw an ashamed look on his face. A guy came in the bar with a gun and threatened to commit suicide, but Sam saved him. But he wasn’t a demon. I don’t know why Dean had to put the holy water on him; all he had to do was ask me. I could sense a demon somewhere in the room, but since there were multiple ones, I couldn’t quite pinpoint one source. I knew they probably all knew I was an angel, so we quickly got out of there, on the search for one of Dean & Sam’s friends, Richie. Dean dropped me and Sam off and he went after the bartender (he had flirted earlier so it would be easier for him to go after her instead of me or Sam). We had an embarrassing encounter with Trotter (Sam didn’t quite trust my demon instincts yet) and then we hurried off, chatting on our way to find Dean.

“Why was he flirting with her?” I asked as we headed to the priest’s house (Sam’s idea, since the bartender demon wasn’t at her house). “Isn’t he meant to be trying to love me?”

“He’s like that,” Sam answered, quickening his walking pace. “Don’t worry, he’s just retaliating. He can’t accept his fate. Once he realises how serious it is, or how stupidly he just treated you, he’ll wake up and be nice. I don’t know if he even trusts you yet.”

“Why? I’m an angel, sent by God, to help him. How could you not trust me?” I questioned, frowning and feeling slightly hurt. Dean had recently been reading through the book I had brought and had been suggesting other ways to try to save him, all which Sam shot down, pointing out the flaws. He didn’t seem too keen to fall in love with me at all, but Sam was certain it was the best way to save Dean. Dean’s reluctancy had made me feel awfully sad and unwanted by the brothers. They needed me. Otherwise God wouldn’t have sent me here to earth to help them.

“I guess your arrival is still a bit of a shock. I’m definitely used to it now though. Dean will be soon too, once he realises how important it is that we have you with us,” Sam explained as we arrived at our destination. The priest was a demon, but he was willing to take us to where Dean was being held captive, so I didn’t say anything to Sam. Besides, my number one priority is to look after Dean. We arrived and the priest revealed to the others he was a demon as well, and Sam got flung to the side. Bobby showed up, only to get thrown to the side as well. At least he trusted me completely straight away, unlike Dean and Sam. I sensed another demon nearby, but not close enough to be any danger to us.

The priest released the other demon woman, and it looked like it was down to me versus them. I started summoning up my powers within, ready to kill the demons inside the poor human hosts. Dean and Sam were both yelling at me, but I shut them out, concentrating hard as the demons trash talked about their relationship together. I took them by surprise, and they lit up, flashing with light and screaming. They fell to the ground together, and the brothers sighed in relief. I turned around and looked at Sam. He gave me a nod in the direction of Dean, and I walked over to Dean’s side. I extended my arm and he gladly took it, helping himself up.

“I guess I underestimated you,” he stated, breathing heavily.

“I guess so,” I said with a small smile. He gave me a tiny one back, which was quite cute. He slightly awkwardly put his arms around me and pulled me gently but firmly into a hug.

“Thanks for helping us,” he whispered in my ear and I couldn’t help but smile and get a funny feeling in my stomach. I looked over at Sam, who was now standing up and smiling at us. He knew we were just beginning our relationship, and hopefully that would save Dean from hell.

“Don’t you mean saving you?” I joked. I had attempted to pick up on the sarcasm and joking nature they had together, and I think I had the hang of it now. Dean pulled out of the hug and had a certain look on his face that told me I had gotten it right.

“Ha. We didn’t need saving, right Sammy? Just a bit of help,” Dean said cockily and he started walking over to Sam. I followed and we left the building, jokingly arguing about whether or not the brothers needed saving by me or not. We jumped into Dean’s car after a quick chat to Bobby, and then we headed our separate ways.

“Have you asked yet?” Sam asked Dean softly in an attempt for me to not hear, I think. I kept on staring out the back passenger window, pretending I hadn’t heard. I heard Dean whisper a ‘no’ back, and then there was silence for a while.

“Uh, Jen!” Dean suddenly said loudly, so it was impossible for me to not hear him. I saw out of the corner of my eye Sam turning away to look out the window, but I knew darn well he’d be listening.

“Mhm?”

“Well, I’m gonna try be a gentleman here, so excuse me if I muck up, I’m not used to it,” he said casually, flashing me a gorgeous and confident smile. I knew what was coming and I knew he knew I couldn’t say no. “Since I find you attractive, funny, and all the rest... and since you ‘saved’ us... I was wondering if you’d let me take you out on a date tomorrow?”

“Real smooth, Dean,” I said, looking back out the window, wondering what would happen to me if I said no.

“So what do you say?” he asked, giving me a broad smile in the rear view mirror.

“Yes,” I replied. Dean smiled a nice grin at me, then hit Sam’s shoulder gently while smiling at him too.

“Hear that? I’ve got a date with an angel!” he announced proudly, and Sam chuckled. I didn’t see the humour in that statement, but couldn’t help but smile to myself. I was going out on a date with the one and only Dean Winchester. The human they couldn’t stop talking about in heaven. And in under a year, we had to fall in love, so Dean could go to Heaven and not hell. Boy, the other angels were not going to let me live this one down if it didn’t work...