Supernatural One-Shots

I Hate You! Or Do I?(Dean Winchester x fem!reader) College AU

(This is based on the movie 10 Things I Hate About You.)

"What's in it for me?" Dean asked his brother and best friend, not looking up from the book. Sam and Castiel had been trying for days to convince Dean to ask you out. "The joy of knowing you helped your best friend?" Dean looked up at Sam with an arched brow. "Come on, Dean. One date so that Cas can ask out her sister. He really likes Meg but she won't date anyone as long as her sister's single."

"What's wrong with her? The sister I mean." Dean had no interest in dating you. He'd seen you around, but you'd always seemed so aloof. So...cold. "She's, well, she's got a bit of a temper and she hates guys that sleep around." Dean let out a laugh, "So you come to the school's playboy?" Dean knew his reputation very well, although it was only about half true. He had gotten around when he was a freshman, but his party days were pretty much over.

"Dean, please?" Castiel asked, giving Dean the puppy eyes. Dean glared at his best friend before looking to Sam and seeing him doing the same. He groaned and agreed. "Fine, but you owe me. Big time. I'll tell you what I want after I talk to the chick. I gotta see what I have to work with." With that, Dean got up and left the library. So much for studying.

The elder Winchester made his way to the school courtyard. He'd seen you there most often. Bingo. You were sitting by yourself at a table off to the side. You were reading and jotting notes, as you often were. Letting himself on more small groan, Dean approached your table. "Hey there, sweetheart," he greeted with a charming smile. You barely glanced up. "No, thank you." Dean frowned. "What?"

You set your pen down and faced him. "No, thank you. I'm not looking for you, Mr. Right. I don't have a band-aid for your scraped knee nor do I have a map for you getting lost in my eyes." Dean blinked in surprise. You had just thrown some of his cheesiest pick-up lines back at him and he hadn't even talked to you yet. "I've heard all your pick-ups, Winchester. You've used them on many women at this school. I figured when your brother and his friend started hanging out with my sister, it wouldn't be long before you finally realized I existed. Well, let me save you some time. I'm not interested." You slammed your book closed and got up from the table leaving a speechless Dean behind.

Dean watched you go. This was going to be harder than he thought. Sam and Castiel definitely owed him big time. However, Dean wasn't one to back down from a challenge either. A small grin appeared on his face. Challenge accepted.

For the next several weeks, Dean tried his best to get your attention, only to irritate you further. "This isn't working, Sam. Forget it." Sam arched a brow at his brother. "The great Dean Winchester giving up on a conquest? It can't be that bad." Dean gave his brother a deadpan look. "Yes, it can. Y/N Macleod cannot be conquered. She's a frickin' puzzle, man." Sam smiled. "You actually like her."

Dean scoffed. "Get real, Sammy. I'm doing Cas a favor." Sam shook his head. "A favor I'm paying for. Which reminds me, you still haven't told me what you want." Dean shrugged. "I haven't decided yet. Believe me, I will let you know." Sam sighed but then glanced across the courtyard. "Look alive. Here comes your girlfriend now."

Dean looked up and saw you approaching the building. "Wish me luck." He got up and walked over to you, hands in his pockets. "You never give up, do you?" you asked him, finally giving him the eye contact he'd been trying to get all along. "Nope. Come on. What's one date?" You rolled your eyes. "With you? The difference between delightfully ignorant bliss and a broken heart."

Dean walked next to you inside in silence for a moment. "Look, I know what people say about me. I'm not gonna deny the rumors, at least not all of them. But I will tell you that I'm not that guy anymore. Give me a chance? Please?" You stopped walking with a deep sigh. "Dean, all guys say that." Dean shrugged slightly. "I know." You must have seen something in his expression because you suddenly gave him a soft nod. "Alright. One chance. Pick me up at 7." Dean beamed and quickly agreed before handing you his phone to put your number in. After that, you turned and walked to your first class and Dean turned back to Sam, giving him a thumbs up.