AUTHOR NOTE: This was requested by follower 1artsypineapple.
Jack was headed back to his room and when he heard a noise from your room. He thought it was odd you were up this late. He knocked on your door. "Y/N?" He called, "can I come in?". He swore he heard you sniffle.
"Sure," you called back weakly. He walked in. Your back was facing your door as you sat on the edge of your bed. He looked around and noticed your phone across the room on the floor like you had thrown it.
"Y/N, are you ok?" he asked.
"I'm fine Jack," you said sniffling again. Your shaky voice betraying you. Jack walked over to you and kneeled down. You looked up at him. He took in your tear stained cheeks and puffy, red eyes.
"what's wrong?" he asked. Before you could even say anything a sob escaped your lips and more tears came. Jack pulled you to him and held you as you cried. He softly patted your back.
"He dumped me," you managed to say, "said he met a closer huntress. I thought he loved me, Jack,". Jack frowned. You were like a sister to him and seeing you heartbroken over some loser broke his heart.
"You can do better Y/N," he said, "he didn't deserve you,". You smiled a little.
"It just hurts is all," you said. He smiled.
"Why don't we go hang out for a while," he suggested, "maybe go to the diner,".
"I'd like that Jack," you said. You washed up your face and grabbed the keys to the car your brothers had given you. You two walked into the garage.
"Let me drive," Jack said, "you can just relax,". You smiled and tossed him your keys. The drive to the diner was silent. You just closed your eyes and enjoyed the wind in your face coming from your half opened car window. At the diner, Jack offered to pay so you both ordered a large thing of fries to share and each a burger and shake. As you ate Jack got you to talk about anything that made you smile. Books, movies, even memories from growing up with Sam and Dean.
"Dean was so mad," you said, "when he woke up and walked into the hotel room bathroom and seen I had made him over with my pretty princess make up kit. He didn't talk to me for like a whole day,". You both laughed. By the time you got back to the bunker, you felt so much better.
"Do you feel better Y/N?" Jack asked as you two walked into the bunker living room. You smiled.
"I feel a lot better Jack," you said giving him a hug, "thank you. You're a good brother,". Jack smiled. He liked the sound of that.