(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.

"You gotta stop cutting off like that, Dean," you told him with a soft giggle, "It makes you sound unintelligent, which I can tell you aren't. I know we don't know each other well yet, but I think that's what makes this kind of conversation easier. No pressure really. No judgment. Just you and me while our mutual friends are out there dancing and drinking." Dean stared at you for a moment before realizing that you were right.

With a sigh, Dean finished his earlier thought. "Lisa...she left me two days after I proposed. She left my six-month-old daughter with me. Hasn't been back since and I haven't heard from her." You reached over and placed a hand on his. "She just left you to raise your daughter on your own?" Dean nodded, making you scowl. "No offense but what a bi-" It was your turn to cut yourself off. You couldn't say that about a woman you didn't know. She may have had a good reason to leave.

Dean gave another small laugh. "Yeah well, I honestly wouldn't change it. Charlie is a great kid, despite having me as a dad. She's smart too, like my brother. I'll probably be able to enroll her in preschool soon." You grinned. "Sounds like you're a pretty amazing dad, Dean. I can tell by the way you talk about her that you give Charlie all the love she could possibly want and need." Dean didn't know how to respond and he wouldn't get a chance. You glanced at your phone and gasped lightly. "I need to go. I'll see you at Benny's in a week?" Dean nodded. You kissed his stubbled cheek and darted from the booth, leaving a confused yet happy Dean behind.

*time skip*

Dean pulled at the collar of his shirt as he tried to prepare himself to get out of the car. "Daddy, I need to potty!" Dean jumped a little at his daughter's sharp tone. He had been so nervous about seeing you again that he had almost forgotten that Charlie needed to use the bathroom. With a chuckle, Dean got out of the car and helped Charlie down. The little girl barely waited a beat before taking off toward Benny's house.

Dean followed quickly after her. Luckily she knew exactly where the bathroom was. Unluckily, there was someone leaving the bathroom as soon as Charlie went barreling in. "Oh!" Charlie pushed passed you. "Sorry. Gotta potty." You laughed. "Hey, when you gotta go, you gotta go." You moved out of the way so she could close the door. You looked up, your eyes meeting Dean's. "I take it that's Charlie." Dean nodded.

For a few moments, neither of you said anything. "Uh, so, I had fun the other night. Getting to know you a little," you said shyly. Dean smiled. "Yeah. Me too. I'm sorry I laid all that out on you." You shook your head, indicating he didn't need to worry. "It's no big deal. In fact, I really didn't mind at all. It's nice to meet someone real in a bar."

"I know what you mean. Anyway. I should probably say hi to Benny." You rolled your eyes. "Good luck with that. He's a bit distracted with the grill and Castiel here. Plus, Gabriel is all over Donna again." Dean laughed again. Of course that would be the case. The door opened again and little Charlie came out. "All done," she declared with a grin. "Good. Charlie, this is Y/N." Charlie's green eyes widened as if in realization. "She's pretty just like you said, Daddy." Dean's face turned bright red, making you chuckle.

"Well I think you are the prettiest little girl I've ever seen. As pretty as a princess." Charlie buried her face into Dean's leg for a second before turning to hug yours. "And you've got a friend for life now." You beamed at him. "I'm honored." Charlie pulled back and grabbed your hand to pull you outside. Dean watched you go with a lightness in his chest. Watching you, someone who didn't know him very well at all, interacting with his daughter in such a carefree manner, warmed Dean's heart.

"You need to ask her out, Dean-o." Dean looked over his shoulder to see Gabriel. He rolled his eyes. "No. I can't." Gabriel frowned. "Look Dean, I don't blame you for being scared after what happened with Lisa, but Y/N isn't Lisa. And if you keep treating every woman you meet like she's going to break your heart, you're gonna miss out on something good." With that, Gabriel went back outside.

Dean sighed. Part of him had to admit that Gabriel was right. He'd been doing that a lot. Pushing people away just so he wouldn't get hurt. And it wasn't doing him or Charlie any good. And now, you were there, right in front of him and he was tempted to do the same thing again. After gathering his thoughts, Dean made his way outside to join everyone else. He scanned for Charlie first, as always. He found her sitting on the grass with you, her gaze focused. It was clear that you were telling Charlie a story that had her intrigued.

He walked over to the two of you. "Hey, Charlie, can I borrow Y/N for a minute?" Charlie pouted for second. "Promise you'll bring her back?" You let out a laugh and Dean smiled. "I promise." Charlie got up and dusted herself off. "Okay, Daddy!" She ran off to find Castiel. "What can I do for you, Dean?" Dean licked his lips. "I was wondering if you'd, uh...crap. I'm not good at this anymore."

You took Dean's hand in yours. "I'd love to go out with you, Dean." He  blinked in surprise. "Really? Even though I'm a single dad who works in a garage?" You scoffed lightly. "What you do for a living doesn't change the kind of man you are. And I think you're an incredibly amazing and strong man. It takes a brave man to raise a little girl on his own. You are just my type of guy and I really want to date you." Dean felt his eyes crinkling as his lips spread into a smile. "That's great." You kissed his cheek again, like you had back at the bar. "It really is. How's next weekend work for you?" Dean squeezed your hand and nodded. "Sounds good."