Supernatural One-Shots

A Date With a Single Dad (Dean Winchester x fem!reader)

(Single parent/no monster AU!)

Dean straightened out his flannel and licked his lips as he looked at himself in the mirror. He kept talking to himself, saying that Sam was right. He needed this. He hadn't left the house for anything other than work since Lisa had left him, leaving their daughter behind. He needed to get out. As much as he loved his daughter, Dean's main adult interaction these days was with Sam and the customers in the garage. So a night out with their friends was just what Dean needed.

He left his room and found Sam in the kitchen with little Charlie. "You sure you're gonna be okay?" Sam rolled his eyes. "Relax, Dean. We'll be fine. Eileen and I got this. We're going to have fun, aren't we, Charlie?" The little girl with Lisa's dark hair and Dean's candy apple eyes looked up at Sam with a toothy grin. "Yep!" Eileen tapped Dean on the shoulder and signed something. Dean had picked up a little sign so he was able to understand his sister-in-law. "I'll try to have fun. Alright. I gotta go. See you later." With that, Dean left the house, but not without one last look back at his daughter.

Dean met Cas, Benny, Gabriel, and Donna at a nearby bar. "There he is!" Donna's voice cut through the music. Dean couldn't help but smile. Donna was always so positive, you couldn't help but be happy around her. "Good ta see ya, brotha. Hope ya don't mind, but I invited a friend ta join us." Dean shrugged. Benny gestured over to the bar and Dean's jaw dropped. Whatever he had been expecting, it wasn't that.

You stood there rather awkwardly, dressed in jeans and a fitted T-shirt, your eyes riveted on Dean. "This here's Y/N. She's one of my cooks at the diner." You gave Dean a smile and offered your hand. Dean had seen his share of pretty women in his life. Hell, Lisa was a gorgeous woman, but there was something about you that made Dean feel like a teenager again. "Nice to meet you, Dean. Benny's told me a lot about you." You spoke firmly, but with a shy confidence, as if you didn't want to come off as arrogant. "Uh, yeah. Nice to meet you."

Dean tried to relax as the night went on. He really did, but it was hard for him. Between worrying about Charlie and having you so close to him, it was difficult. Benny and Donna had insisted that you and Dean sit together, especially since Gabriel had his arm slung around Donna's shoulders the entire night. Dean knew they were up to something, but couldn't figure out what exactly they expected to happen.

"Do I make you nervous, Dean?" your soft voice came from next to him. He almost didn't hear it. Almost. He turned his gaze to you. "No, sweetheart. It's not you. I haven't been out in a while. Guess I'm a little rusty," he replied with a chuckle. You smiled. "I guess that makes sense. I'm really sorry about Benny forcing me on you. He's been after me for months to get out. He's been dying for us to meet before his next cook out." Dean's brows furrowed. "Really?" You nodded.

"Yeah. Not sure why, but then again Benny doesn't share unless he wants to. He did say something once about the two of us becoming good friends. Maybe something more." Dean wanted to groan. Of course Benny was trying to set him up. "Look, sweetheart, you don't wanna get involved with me. I've got..." he trailed off, unsure of how to say it. He loved his daughter more than anything, but something was stopping him from scaring you away. He actually really wanted to get to know you a little better.

"You've got...baggage? We all do." Dean shrugged a little. "I wouldn't say baggage. But yeah, I guess." You cocked your head to the side. "You married?" Dean laughed bitterly. "Not in the slightest. I had a girlfriend a few years ago. Even proposed. That's when she decided she didn't want to settle down. She up and left, leaving my dau-" Dean cursed himself. He was revealing way too much.