Description:Dean asks out the reader and they tell him they'll only go if it's something that hasn't been done a million times before.

Reader Pronouns:They/Them

Any AUs or Music? Inspired by 'It's All Been Done' by Barenaked Ladies. No AUs.

Today was the day. Today was the day Dean was finally going to grow a pair and ask out Y/N. They'd never been on more than one date with anyone in town before, and Dean should know. The two of them had been hunting buddies for forever. Dean flipped on the radio and drove to the local bar where Y/N was meeting him to 'discuss a hunt he'd found'. Total lie, by the way. He pulled into the lot and paused to check how he looked one last time. He straightened his jacket and tausled his hair for the millionth time before jumping out of the Impala and gently closing the door. 

"Wish me luck, Baby." He muttered as he locked the faithful car. He turned, and strutted inside to see them already clutching a beer with his favorite drink set out next to them with a napkin over it. He plopped onto the stool and pulled the napkin off. "Hey, Y/N. How's it going?" They looked over at him with a smile. 

"It's going. You mentioned a hunt on the phone, said it might be urgent. Is it a nest or something?" Dean shook his head at the carefully chosen verbal disguise for a vampire case. 

"No, there isn't a hunt. I just wanted to meet up with you. Had something important to ask you." He took a small sip of the liquid courage, savoring the way it burned his throat on the way down. 

"And you couldn't ask me on the phone?" They deadpanned. 

"Not really, you're a bit too important to me for me to just ask you out over a phone call." Y/N raised an eyebrow. 

"Asking me out? Finally grew a pair?" Dean smiled at the familiar phrasing he'd only just this morning used to describe the situation. 

"Yeah, I guess so. Is that a yes?" He may have sounded suave on the outside, but internally he was chanting, please say yes, please say yes! 

"Sure." Y/N said, Dean pumping a fist in victory. "On one condition." He lowered his fist. 

"Yeah?" 

"It can't be a stereotypical date. No bars, no minigolf, and please God not dinner and a movie or some picnic in the woods." Dean smirked. Being different. Now that is something he excelled at. 

"Easy. May I ask why?" 

"It's all been done before. If I want to get to know someone, I want to see what they think is fun or enjoyable. Not some rinky dink idea they got from a chick flick." Damn, they really were perfect. 

"You got it. I'll pick you up at seven, wear something you could hop a fence in." Dean finished his drink and stood, paying for both before Y/N could stop him, winking on his way out. Unique date ideas...he knew just the place someone like Y/N would like.

Part Two?