Jack Kline

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You let out a sigh as you walk into the bunker and head down the steps only to find an awake Jack Kline staring up at you

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You let out a sigh as you walk into the bunker and head down the steps only to find an awake Jack Kline staring up at you.

"Hey, Jack. What are you doing still up?" You ask curiously as you make it to the bottom of the stairs

Normally Jack is asleep or in his bedroom by this hour as it's now almost midnight.

"I....uh, I couldn't sleep." answers Jack softly as he looks at you before his eyes drift away

That was the truth Jack couldn't sleep because you were out on a date with some guy. Dean had made a joke that you wouldn't return home tonight and Jack recently got the talk from Sam so he knew what you would be doing if you weren't home. Jack has a crush on you so he didn't even want to go on the date and he definitely didn't want you to do that with the man.

"Did you have a nightmare?" You ask softly as you walk towards the blue-eyed boy, worried

"No...I just couldn't sleep." answers Jack with a shake of his head knowing you were concerned as he looks into your eyes

Jack could never lie to you even if he tried.

"How-how was your date?" asks Jack changing the subject quickly, while trying to keep the jealous edge to his voice hidden attempting to play it off as curious

You let out a huff of air at his question.

"Horrible." You answer as you head towards your bedroom with Jack trailing behind you

Jack couldn't help but feel a bit happy at your answer glad there was not going to be a second date with the man named Brad. Though once he saw your upset face as you plopped onto your bed his emotions quickly changed.

"Are you okay?" asks Jack plopping down next to you

Your fingers play with your other ones a nervous habit you had.

"I don't know." You sigh

"What happened?" follows up Jack watching your facial expression

"I like him, he was nice when he asked me out and super nice. I went out bought this dress and got all ready, I was just really looking forward to this. Then we go on this date and...He just....all he wanted was to get in my pants. It was so frustrating." You explain

Jack nods because even though he has no clue what "get in my pants" means he can tell that it's a bad thing by your tone and expression.

"He was a jerk." comments Jack making you chuckle

"Yeah, he was." You say facing Jack before you cuddle up to him

Jack smiles softly at this action as he puts an arm around you bringing you a little closer before he moves his hand to gently rub your back soothingly.

A few minutes go by before Jack suddenly breaks the peaceful silence.

"Y/N......I want to take you out on a date." says Jack looking down at you

"Huh?" You say as you look up at him with a surprised expression on your face

"I want to take you out on a date. promise I won't be a jerk and I won't try to get into your pants. I just...I really like you." stumbles out Jack with a sweet, shy smile

"I think a date with you...will probably be the best I've had in a while so why not? It'll be fun." You say with a small smile

Jack's sweet smile quickly turns into one of a giant, toothy grin.

"Awesome, this is going to be so great." says Jack with so much happiness you could have thought you told him that he is going to Disney World

You couldn't help giggle and smile at his enthusiasm before you lean up to press a kiss to Jack's cheek. Jack's face quickly going in flamed by this affectionate action.

"You want to stay in here tonight and cuddle?" You ask while looking at Jack with a goofy smile

Even though you thought it would be physically impossible, Jack's grin grows even more. His favorite thing ever is to cuddle with you.

"Of course." answers Jack excitedly

You chuckle before you rest your head back on chest after Jack moves to a more cuddly position.

The two of you feel asleep that night with huge smiles on your faces as both of you are quite excited for what is to come from this development.

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⚠️Season 13 Finale Spoilers⚠️

I don't think Jack lost his grace because his neck was still glowing when Lucifer healed the cut. When Cas lost his grace his cut was not glowing it was red like it you were to cut a human. I'm just making a guess here but I think Jack still has his grace which means he still has his powers.

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