(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.

Dean picked you up at 7 on the dot. "I really hope you're hungry," he said as he lead you out to his car. You gave a low whistle. "She's a beauty. '67?" Once again, you'd surprised the man. "Uh, yeah. You know cars?" You moved your head from side-to-side in a "kind of" motion. "I know a little. My dad insisted that we have at least the basic knowledge of cars before he would by us our first." Dean opened the door for you before running around to the driver's side.

Dean drove you to this cute little diner. Not what you expected from the guy. "Is this alright?" You smiled. "Yeah. It's nice." Dean grinned and got out of the car. You barely had your hand on the door handle before it opened. Dean offered you an arm. "My lady?" You could fight your giggle as you took it and let him lead you into the diner.

"Dean! I didn't expect to see you here tonight!"a friendly looking blonde greeted. You instantly felt small next to her. She was gorgeous and probably one of Dean's old flings. Dean smiled at her. "Hey, Jess." Jess motioned to a booth and came around the counter with menus. "Hi. I'm Jess," she said to you, extending her hand. Slowly, you took it and shook it. "Y/N."

Jess talked for a couple minutes before taking your drink order and going back behind the counter. "Old girlfriend?" you asked Dean as soon as she was out of earshot. Dean's eyes widened and you could really see the green in them. "No. Jess is Sam's girlfriend. I think he's gonna marry her one day." You felt yourself flush at your jump to the wrong conclusion."Look, Y/N I meant it when I said I've changed."

For the rest of the time at the table, the two of you actually talked, getting to know one another. Dean wasn't as bad as you originally thought. True, he was a major flirt, but he was also genuinely sweet and charming. He was really intelligent too, although he didn't seem to think so. He was going to school to be a mechanic and help in his dad's garage. That was how he'd ended up with the Impala in the parking lot. "I fixed her up myself and when I was done, Dad gave her to me as a gift." You smiled. Dean also realized that his first impressions of you had been wrong too.

You weren't cold at all. You kept your guard up because you'd been hurt before. You'd had a boyfriend who treated you poorly. That was why you didn't really trust Dean. You were also dedicated to your studies, but you were a business major. Being the older daughter, your father wanted you to take over his business. You had a great sense of humor.

Jess came back to the table. "Here, Dean. Your favorite." She slide a piece of pie in front of both of you. "Thanks, Jess. You should just go ahead and bring me a second piece to take home." Jess giggled and nodded. "Before I dig in, I have to hit the bathroom. I'll be back in a minute." Dean slid out of the booth and Jess slid in.

"He likes you." Your brows furrowed and she sighed happily. "Dean always comes in here alone. Even when he was dating a new girl every week, he'd come here alone or with Sam and Cas. He'd enjoy his pie and then leave. He always takes his dates to the fancier places because this place is his sanctuary. His little getaway. Him bringing you here tells me that he really likes you." Jess got up, leaving you to your thoughts.

Dean came back a minute later and you were still staring off into space. "Everything okay?" You came back to reality and smiled. "Yeah. Everything's great." Dean nodded and dug into his pie with vigor. You'd never seen a man enjoy pie so much. His cheeks were full when he looked up at you. "What?" You giggled at the crumbs of pie crust and filling all over his face. "You're a mess, Dean Winchester." He hummed in agreement before shoveling another bite into his mouth.

Your date ended on a high note. Dean walked you back to your dorm, hand-in-hand. "I actually had a really good time tonight, Dean. Thank you." Dean chuckled and pouted playfully. "Did you doubt me?" You joined in his laughter. "In all seriousness, I did too. Could we do this again?" You bit your lip and nodded. "I'd like that." You reached the door of your dorm room and Dean leaned in and kissed your cheek. "See you tomorrow?" You nodded and entered your room.

*time skip*

You and Dean went on several dates over the next couple of months and Dean realized that he was actually falling for you. You weren't like all the other girls he'd been with before. Yes, you were stunning like they were, but your beauty wasn't just skin deep. He didn't want to stop seeing you. He was even beginning to regret that he hadn't asked you out before. He felt even more guilty about the fact that Sam was still bugging him about repaying him for the favor.

Dean was sitting at table waiting for you when Castiel approached him. "Dean." Dean glanced at his best friend. "The deal is off." Dean's neutral expression turned to one of confusion. "What?" Castiel took his hands out the pockets of the trench coat he always wore. "I said the deal is off. Meg never wanted to go out with me. You don't have to date Y/N anymore. Sam and I will make sure to hold up our end of the bargain, but you don't have to pretend to like Y/N anymore."

"You were just pretending?" a soft voice spoke up and Dean froze. He turned to find you standing there, staring at him with wide, watery eyes. "I fell for it. I fell for it all. I can't believe I thought you'd changed. Go to Hell, Dean Winchester." You turned and stomped away. "Y/N!" You didn't stop. You made your way to your car, no longer in the mood to go to class.

You made it to the car before you felt someone grab your upper arm. "Let me go!" you cried. "Please, just listen to me, Y/N." Dean could see the rage on your face. "Why should I?!" He let you go and sighed. "Please, Y/N." You shook your head and opened your car door. "So you can tell me more lies? No, thank you." Dean felt himself flinch as you threw the very first words you'd said at him again. You climbed in the car. Dean backed away, letting you drive off, his heart sinking in his chest.

For the next few days, Dean walked around in a haze. He missed you. Whenever he saw you around campus, he felt even worse. Unlike most women, who would have probably looked terrible after a break up, you had decided not to wallow in your misery. You looked incredible, as if to spite Dean. When you saw him, you just ignored him, which just served to make Dean feel ten times worse.

"Dude, you're miserable," Sam said to him one day. Dean didn't deny it. "Just go talk to her. Apologize." Dean groaned loudly. "Don't think I've tried, Sammy?! I have tried everything I could think of to get her to talk to me. I messed up too bad this time." Sam huffed and got up. Ignoring Dean's calls for him, Sam went in search of you. He found you leaving the library.

"I need to talk to you, Y/N," Sam said, catching you off guard. "Why?" Sam gently took your arm and lead you to an empty room. "Dean is miserable." You scoffed although inside you were still upset. "Dean brought it on himself." Sam shook his head. "No, he really didn't. Cas and I did." Your brows furrowed. You had only heard part of Castiel's and Dean's conversation.

Sam sighed heavily. "Look, Cas has liked your sister for a while now, but he knew that, as long as you were single, Meg wouldn't go out with him. I have Jess so we asked Dean to ask you out. For Cas' sake. Then, when you and Dean started hitting it off, we didn't believe it was real. When months went by and Cas still had no luck with your sister, he felt bad for having Dean continue the charade. We didn't realize that Dean had real feelings for you."

You didn't answer for a second. Then, you asked, "Why didn't he just tell me?" Sam chuckled softly. "Because that's Dean. He doesn't handle deep feelings well. And it would be a huge shot to his ego for anyone to know that he made a bargain to go out with the girl that he ended up falling in love with." Sam gave your shoulder a little squeeze. "What can I do?" you asked. "Talk to him." You nodded and Sam left the room.

You walked out a few minutes later, eyes scanning everywhere for Dean. You found him leaning against his precious Impala, holding a box in his hands. You made your way over there, the words you wanted to say bouncing around in your head like children who'd had too much sugar. "Dean," you breathed when you finally reached him.

"Y-Y/N? I am so sorry. I should have just told you. Actually, I never should have agreed in the first place. I should have asked you out on my own." Dean handed the box over to you. "I, uh, got you this as a something of an apology." You lifted the lid to find a slice of Dean's favorite by from the diner. You knew how much he loved his pie and here he was, offering it to you. All the words you'd planned to say flew out of your head.

You took the pie and set it on the roof of the car. You wrapped your arms around his neck and kissed him. It was your first actual kiss with the man and boy was the wait worth it. You pulled back and said, "You can't just get me a piece of pie every time you mess up." Dean chuckled. "I know, but I'm sure I can find other ways." He kissed the tip of your nose before moving to your lips again.