Supernatural Imagines (On Hiatus)

Jack Kline (Requested)

Requested by @bowwiiii

Jack Kline couldn't help but stare at Taylor, the cute waitress at Dean's favorite diner that luckily happens to be around Jack's age. Taylor is currently on her break so she's sitting at the bar sipping on a soda while looking at her phone.

"Dude, you keep staring at her like and you might be getting a restraining order." says Dean as he takes a sip of his drink with a raised brow

"Huh?" asks Jack confused as he finally removes his eyes from Taylor

"Jack, why don't you just go talk to her?" asks Sam, who had noticed Jack would stare at the certain brown haired waitress every time they came here

"I don't know how to. I've never talked to a pretty girl before. I don't know how to talk to them like Dean does." answers Jack as he looks at Sam

"Don't sweat it, kid, nobody can be as smooth as me." says Dean with a smirk while Sam shots him his famous bitch face

"Jack, just be nice and be yourself I'm sure she'll like you." suggests Sam making Jack feel a bit less nervous

"Just don't screw it up, I like the food and if you really mess things up then we can't ever come back." says Dean making Jack twice as nervous

Dean will be really grumbly if he can't get the pie here ever again. Thinks Jack with a scared look on his face

"Just ignore him, you'll do great...Just don't mention the whole your Lucifer's son thing." instructs Sam

"Okay." breathes out Jack

"Well, go get her champ." says Dean before popping a fry into his mouth

Jack slowly stands up a nervous look on his face before he makes his way to the green eyed girl.

"Hey, T-Taylor." says Jack shyly

"Hey, did you guys need something?" asks Taylor with a small smile

"No, no, I....um, I just came over her to-" starts Jack flustered and nervously

"He is so going to strike out." says Dean as he pops yet another fry in his mouth

"Bet you twenty bucks he doesn't." says Sam with a determined look

"Oh, man you got it. I'm going to be twenty bucks richer today." says Dean with a confident smirk

"We'll see about that." says Sam returning his eyes to Jack

"I-I came over here to....to ask you-" rambles Jack before he stops for a second to take in a deep breath

Taylor's green eyes look at Jack curiosity bubbling in her.

"I wanted to know if you would like to go out sometime?" asks Jack looking at Taylor with his adorable puppy dog eyes

"Sure." answers Taylor with a grin

If Taylor was telling the truth the cute boy in front of her and the two other men he was normally with are her favorite customers. Not only did they tip well, but they are all fairly attractive. Taylor found Jack the best looking with his adorable puppy dog eyes and excitement made him quite irresistible.

"Really?" questions Jack quite excitedly

"Yeah." replies Taylor with a small chuckle

"G-great, um, how about five tomorrow?" asks Jack with a grin so big it put Julia Roberts to shame

"That's perfect." says Taylor placing her hand on top of Jack's that was resting on the counter

"Dang it!" groans Dean, who quickly realizes he had lost the wager he made with his brother, while Jack and Taylor exchange numbers