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
Sam shoots him a victory smile as he holds his hand out for the twenty he is owed.
"Stupid spawn of Satan." mumbles Dean whole he pulls his wallet out before slamming the twenty in Sam's hand
Jack bounces up to the brother the huge smile still on his face as he grips the piece of paper with Taylor's number on it tightly.
"She said yes." announced Jack happily as he waves the paper in his hands
"That's great, Jack." says Sam patting the boy's back
"Yeah, just great." mutters Dean grumpily
Even Dean's grumpy mood couldn't make Jack's smile waver.
I have a date with the prettiest girl in the world. Thinks Jack as he bounces slightly from his excitement
"Sam, I need your help." announces Jack two days later, a few hours before he was supposed to meet Taylor at the movies
"What's wrong?" asks Sam looking up from his lore book
"I need help deciding what to wear for my date." answers Jack
"Oh, I can fix that." says Sam confidently
Taylor stands in her room looking through her closet a huff leaving her mouth as she can't quite seem to find the perfect outfit.
"It has to be perfect." murmurs Taylor softly hoping to find an outfit to impress Jack
I don't think I've ever been this nervous for a date before. Thinks Taylor as continues to search in her closet
"What the hell are you wearing?" asks Dean as Jack slides into the passenger seat of the Impala
Dean had to drive the movie to his date since Jack has no clue how to drive and Sam has a date with a cute librarian.
"Sam dressed me." answers Jack proudly thinking his apparel was good
The red flannel he wore with a white undershirt along with the jeans he is wearing made him feel like a Winchester.
"Jack, it has a blood stain on it." points out Dean looking at the nicely sized blood stain on the chest area
"Oh." says Jack slightly up upset
"Should I change?" asks Jack looking at Dean
"We don't really have time." replies Dean looking at the clock
Dean quickly took in the panic looks on Jack's face before he lets out a sigh
"Take the flannel off." instructs Dean and Jack immediately complies as Dean turns around looking at the back of Baby for something
"Come on, come on." mumbles Dean before he finally feels what he was looking for
"Ah, here we go." smiles Dean as he pulls the older more worn leather jacket from the back
"Put it on." commands Dean before he turns Baby on
Jack shrugs the jacket on looking down at himself to see if it looked good.
"Thanks, Dean." says Jack as the confident smile returns to his face
"No problem, kid." says Dean as he pulls out of the garage
Jack stands in front of the movie theatre nervously rocking back and forth on his heels. He had never been so nervous in all his life.
"Hey." says Taylor as she walks up to Jack giving him a smile
"Hey." says Jack with a nervous smile before Taylor wraps her arms around the blue-eyed pulling him into a hug
Jack hugs her back instantly feeling his nervousness melt away a little. Taylor pulls away from him a little still keeping an arm around Jack's waist.
"You excited for the movie?" asks Taylor sweetly
"Yeah, I can't wait." answers Jack smiling down at Taylor as he slings an arm around her shoulders
Taylor and Jack made their way into the movie theater chatting happily.
The date went surprisingly perfect. Jack did the smooth move that Dean taught him. He fake yawned and then put his arm around Taylor, who cuddled up to him with a smile. The movie the Jack plus Taylor saw was great and they both enjoyed it very much. Thought Jack didn't watch most of the movie as he was to busy sneaking glances at Taylor. Jack even got the confidence to grab Taylor's hand intertwining their fingers as they watched out of the movie together. Taylor had blush slightly and Jack couldn't help but think that she looked stunning with that slight flush to her cheeks.
"I hate a great time tonight." says Taylor as Jack and her stand outside the theater
"Me too." says Jack with a smile
"Do you think we could do this again sometime?" asks Jack a little nervousness evident in his voice
"I would love that." answers Taylor beaming with joy
Jack's grin grows before another piece of advice Dean gave him popped into his head. Jack's hand reaches up to gently cup Taylor's cheek as Taylor looks into Jack's bright blue eyes. Taylor's hands gently move to the sides of Jack's waist. Jack gives a small smile to Taylor before he finally leans down and presses a sweet kiss to Taylor's lips.
"That's my boy!" says Dean proudly as he fist bumps the air with a smile while watching Taylor and Jack kiss
"That's my boy."
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Honestly, I'm low key proud of this one and normally I always think I can write my imagines better, especially requests. Dean and Jack are both super cute in this.