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Updated April 27 2020

Emma Winchester: P.O.V.

I was getting ready for my date with Jack when one of Dean's best friend came in to help me get ready for this date. She was about my height and she loved to do makeup. I was nervous for this date with Jack, I don't know if its because he's in a gang or just because this is my first ever date. 

Cora was putting on the finishing touching with my makeup when Dean came in to see how it was going. 

"Wow Emma you look beautiful" Dean said with a smile

"Thank you, Cora helped me a lot" I said putting on my shoes. 

They all walked out of my room leaving me to look myself over one last time. 

Dress:

Makeup:

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Makeup:

Makeup:

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Hair:

I walked downstairs to see my brother talking to Jack they seemed to be having a good conversation until Jack saw me at the end of the stairs

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I walked downstairs to see my brother talking to Jack they seemed to be having a good conversation until Jack saw me at the end of the stairs. He smiled standing up 

"You look gorgeous Emma" Jack said 

We said bye to my brother and made our way to his car. It was pretty nice but being a gang must get you a lot of money 

I said bye to dean and we headed to his car, for a kid in high school he has a nice ass car. His car is way nicer than any high school kid with a car.

He drove us to the restaurant and when we arrived we made our way inside. I saw the hostiest checking him out which made me a little jealous but he ignored it telling her table for two and us making our way to a table in the very back. 

"This place is beautiful but we could of gone some place less fancy" I said opening my menu

"I wanted to take you somewhere romantic and special" He said 

"I didn't come from much, Jack. I would of been okay with some fast food place" 

The waitress came up to us and kept making eyes at Jack. I just ignored it and ordered my food 

"I'll take the Chicken Alfredo and water" I said handing her my menu with a little glare. 

"I will have the same with a Pepsi instead of water" He said handing her the menu with a chuckle

She walked away and I looked at him 

"Why did you just laugh?" I asked 

"You're jealous of a girl I have given no attention to" He said 

"I am not, Jack" 

"Sure you aren't gorgeous" He said 

When our food came she sat it down and slide something to Jack who didn't seem to glance at it. I on the other hand was kinda curious as to what it was but didn't want to seem nosy. I just left it alone and ate my food and when he noticed it he called the manager over. 

"Yes, Mr. Gilinsky?' He asked 

"Your waitress is being very rude. She keeps flirting with me and she gives my date here dirty looks. I will not tolerate this from her" He said 

"I will get right on it sir. I am very sorry for that. Your meal is on me tonight" 

We watched him walk away and Jack looked at me with a smile on his face and then grabbed my hand and pulled me out of the restaurant and drove us to a little part on the beach. 

"Jack?" He looked down at me waiting for me to say something 

"Why are you in a gang? You have a life you could be getting" I said

"My parent did drugs when I was young and refused to take care of me so I fell into the wrong crowd and as I got older I got into a gang and became feared by many but you don't looked scared of me one bit which makes me kinda happy" Jack said smiling 

"You are himan Jack and deserve to be loved by people and not feared by people. You are a person to me who just wants to be loved" I said 

We had decided that it was time that I headed home because it was getting close to my curfew. We pulled up ro to my house and he walked me up to the door. 

"I actually had a great time tonight, Jack" I said 

"Maybe you will let me take you out some other time" He said 

"I might just take you up on the offer" 

He leaned down and connected his lips with mine, we stayed like that for a few seconds. The porch light started flickering and we saw Dean standing in the window laughing. 

"Goodnight Jack" I said giving him a quick kiss

"Goodnight Emma" He smiled walking to his car, he waited till I was in the house before he drove off. 

"How was the date Emma?" I heard when I walked in the house. I saw Castiel and Dean sitting together on the couch Dean having a smirk on his face. 

"It was amazing well until Dean flicked the porch light on and off" I said hitting him in the back of the head. 

"Go change and we can watch a movie together" Cas said. 

I ran up to my room and changed taking off my makeup and coming back down to see them starting a movie. I sat on the chair in the living room and we decided on a horror movie. We spent the rest of the night watching movies. 

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