Here is a story written
By @writingismydrug
Imagine: Going on a date with Jack
Title: Curious Feeling
You were new to the Mills household. Another girl Jody took in after being saved from a witch who was using you to lure in young boys for a youth spell. You had become good friends with the other girls especially Claire. She seemed to be the rebel type in many ways. You were helping Claire and Alex set the table. Jody was expecting old friends over for dinner.
“So who are these guys?” you asked placing plates on the table.
“They are hunters Jody met a while back,” Alex said, “she kinda adopted them as big, adult children,” they all laughed. Soon the table was ready as Jody and Donna worked on making homemade beef stew and rolls. There was soon knocking on the door. Claire opened it to reveal two guys dressed in flannel shirts and jeans, a guy in a trench coat, and a younger boy about your age. They hugged everyone as they made their way into the dining room.
“Who is this?” Sam asked.
“Oh Y/N this is Sam and Dean Winchester, Castiel he’s an angel, and this is Jack,” she introduced, “guys this is Y/N, A new addition to the wayward sister house,”. They all waved at her. Jack smiled and waved at you and you found yourself looking down at the floor to hide a blush that was forming on your cheeks.
“Dinner will be done soon guys,” Jody said, “hope you're hungry,”.
“Starving actually,” Dean said. You were all soon sitting at the table eating. Castiel more observed then ate as he asked Claire tons of questions. Every now and then Jack would lock eyes with you and smile. You would smile back shyly and look down at your hands. You didn’t understand why you felt so weird every time he looked at you. He was cute. He had short, wavy, light brown hair and brown eyes. He had the cutest little smile of any guy you’ve ever seen. Dinner went smoothly as Jody filled the boys in on the whole witch thing. You just wanted to forget about it.
Later that night Jody had shown the boys to the guest room. There were two beds and a sofa in the room. Jack settled for the sofa as he didn’t sleep much. Castiel noticed the young nephilim lost in thought.
“You alright Jack?” he asked.
“I’m fine,” he said, “guys how do I ask a girl out?”. That took all three boys by surprise.
“Who do you wanna ask out Jack?” Sam asked. Jack smiled.
“Y/N,” she said, “she’s really nice and she’s very pretty,”.
“Kids got good taste,” Dean said finishing off another beer.
“Just ask her politely,” Sam said, “we’re staying in town a few days,”.
“Thank you, Sam,” Jack said as he headed off to find you. He found you curled up on the couch reading. He sat down in a chair across from you. “Hello Y/N,” he greeted. You looked up from your book.
“Oh hi Jack,” you said placing your bookmark in between the pages you were on and closed your book.
“May I ask you something?” Jack said looking at you with those sweet, puppy eyes.
“Sure,” you said sitting up, “what’s up?”.
“Would you mind going out with me tomorrow?” he asked, “like a date?”. He looked down. He was just too cute.
“I’d like that Jack,” you smiled.
“Then until tomorrow Y/N,” he said getting up and walking back to the room.
The next night you got ready. You put on a white dress with a matching pair of wedges and you put your hair in a neat bun. You applied eyeliner and some lip gloss. Just as you finished getting ready there was a knock on the bedroom door. You grabbed your purse and opened the door. Jack was standing there. He was dressed in a pair of nice jeans, a dress shirt, and his hair was combed back.
“You look beautiful,” Jack said handing you a small red rose.
“Thank you, Jack,” you said blushing, “you look very handsome,”. He smiled.
“Are you ready?” he asked. You nodded as he held out his arm for you and took it. They walked to the front door and Castiel informed them he would be the driver. You all walked outside and piled into Cas’s car. He drove to a small little diner and you both got out. You walked in and took a seat in a booth by a window.
“Please, order anything you want,” Jack said, “the guys made sure I had enough money,”.
“Thank you, Jack, “you said skimming the menu. You ordered a pizza to share and two chocolate milkshakes. You mostly talked about Jack. He told you how he was born and how the boys took him in. He and Claire were both basically adopted by Castiel. When you got back Jack insisted on walking you to your room.
“I had fun,” Jack said that adorable smile on his face.
“I did too,” you said opening the door to your room, “thank you so much, Jack,” You kissed his cheek and went into your room closing the door. He touched his cheek and his smile grew wider.
