Hello everyone! I hope your weekend is off to a great start! This story will be posted in three parts. It was an insanely fun one that the fabulous Emma Winchester 424 and I wrote many years ago, and I hope you enjoy it as much as we did. Be sure to check out Emma Winchester 424's Dean/daughter fic - it'll literally blow your socks off.

These chapters will contain a lot of hilariously awkward Uncle Dean and fluff :) A perfect combo, right?

Read, Review, but most importantly, ENJOY!

Sam slowly sipped his glass of water at the dinner table, where he was joined by his four-and-a-half-year-old daughter Emily and his older brother Dean. Sam could feel butterflies in his stomach from sheer nerves—he had a date tonight. It was the first real date he'd had since his wife passed away suddenly over two years ago. He knew he had to get over the paralyzing fear that he was doing something wrong. Sarah would want him to live his life and not be a grieving widower forever. She would tell him to embrace happiness with no regrets. But that didn't calm his nerves, much less after he realized he had no actual idea how to date anymore—but that wasn't something he could say out loud to his brother who could make any girl's panties drop with a single look.

Emily took another large bite of pizza, enjoying the fact that Uncle Dean had been able to convince her dad to get it—the only compromise had been to fill it with vegetables at least. Once she swallowed, she stared at her father across the table for a moment, noticing he lacked a plate of food in front of him. "How come you don't eat with us?" she asked with curiosity.

Sam sat his water down gently. "Because I'm going to eat a little later," he reminded gently. He'd already explained to her what was happening tonight, which was why he made sure Dean could be here. He wasn't sure how Emily was going to do without him here, and he didn't want just anyone to deal with that. Sure, Dean had babysat her on many occasions, but this would be the first time he put her to bed without Sam being in the house. And he honestly didn't know how his little girl was going to react. So it was best that family was there.

Emily nodded once. "But what are you going to eat?"

Sam shrugged. "Not sure yet, maybe some steak and potatoes." Maybe his date would like the nice steak place downtown tonight.

Emily sat the piece of pizza back down on her plate as if changing her mind about it. "Can I eat with you, too?"

Sam took a stilling breath before responding. "You won't be with me, Em. You're going to hang out with Uncle Dean tonight, remember?"

Emily's eyes narrowed for a moment. She knew that he'd told her this already, but she didn't like it. Her dad was going to do something that she wasn't invited to and it didn't feel right to her. They did everything together after all. She looked over to Dean, as if analyzing his appearance, deciding if it was worth hanging out with him tonight instead of going out with her dad (as if she had a choice).

Dean could see the dilemma, and through a mouthful of pizza, Dean commented, "C'mon kid- we're going to have a great time. We'll get a keg, light some firecrackers, call some stri-"

Sam let out a loud cough mixed with the bitch face to cut off Dean. However, that didn't stop the little girl from picking up on his words with genuine curiosity. She loved learning new words. Emily looked at her dad innocently. "Hey Dad? What's a keg?"

Sam's bitch face intensified toward Dean before his attention returned to his daughter. He replied simply and definitively, trying to leave no room for more questions, "It's something for adults."

Emily nodded her head, complacent with his response. "Okay." She took another bite of pizza.

Sam reached over and rubbed her arm gently. "You're going to have a lot of fun with your uncle tonight, peanut."

She reveled in the affection and her nickname, and there was a brief moment of silence before Emily spoke up again. In true four-year-old fashion, she was already moving on to other ideas now that she knew she'd be staying with her uncle. "Hey Uncle Dean, can we watch a princess movie?"

Dean nearly choked at hearing her words, but with great effort, he swallowed his mouth full of food. "You can. Knock yourself out."

The emphasis on "you" was completely missed. "I think we should watch Aladdin because you never see-d it." Sam bit his bottom lip to keep from laughing. He loved it when unexpected payback happened before his eyes.

"Aladdin, huh?" He could see Sam laughing at him, so he manned up. "Alright. Aladdin. Cool. Bring it on." He got up and crossed to the fridge. If he was going to be subjected to princess crap, he needed more beer. He threw casually over his shoulder, "Then afterwards, how about ice cream?" Two could play at this game, Samuel.

Sam turned in his seat so Dean could clearly see that he was grinning just as wide. "Sure. You can have all the ice cream you want. Uncle Dean will be here to play all night long." It was Sam's subtle way of reminding Dean he'd be the one putting her to bed, so he was going to have to deal with the sugar high.

Emily clapped her hands together and exclaimed triumphantly. "PRINCESSES AND ICE CREAM!" It was like her birthday!

Dean shrugged, pretending not to care. How bad could a sugar high be? He wasn't worried. "That's right, kid. And your dad is going to be getting plenty of sugar himself tonight, too." He gave Sam his shit eating grin as he returned to the table.

Her eyes light up. "Are you getting ice cream too?!"

However, his bitch face softened when he saw her adorable blue eyes. "Probably not, Em. Just doing dinner and a movie with Beth."

Emily took another bite of pizza and stated matter-of-factly, "I bet she'd like ice cream, Daddy. Don't be mean to her and say no like you do to me and Uncle De sometimes."

"Yeah, Sam. Definitely don't say no to anything she wants." Dean was so proud of his niece- she couldn't have set him up better for that one.

Sam's eyes narrowed slightly and he said directly to Dean with an undertone that he didn't like what his brother was implying. "There will be none of that tonight." He wasn't ready for that yet. It needed to be one tiny step at a time.

Emily chimed in again almost with a scolding voice at hearing his tone. "Remember to be nice, Daddy."

Sam quipped back without hesitation to keep Dean off his case. "If I give her everything she asks for now, then she won't have anything to look forward to later."

Emily pondered this for a moment until she swallowed. "Is that why you don't take me to Disney World yet to see the princesses? 'Cause I ask-ed you a lot."

Sam couldn't hold back a small chuckle. "Exactly, Em. It's so you have something to look forward to later." When in reality, he planned to put that off as long as he could—preferably forever. Large crowd? Long lines? Princesses galore? He wasn't built to deal with that.

Dean leaned forward and directed his next statement at Emily. "Yeah. Or maybe you give someone what they ask for right off the bat, and then they realize that it's not nearly as good as they thought it would be." He grinned lasciviously at his brother, then crammed the last bite of pizza in his mouth. Once he could see that he won this argument, he asked, "So- what are you and this chick doing tonight?

Emily was gleefully oblivious to all the hidden messages, but Sam was painfully aware of them, and thankful that she had no idea. Dean was probably right after all—Sam had no freaking idea what he was doing, and Beth was sure to be disappointed in the end. However, after taking another sip of water, he needed to change the subject and not dwell on the inevitable. "I think we will go grab dinner at St. Elmo's and then grab a movie later tonight." He felt his insides turn from anxiousness about the upcoming date. He waited to hear his brother's opinion, even though he was trying to act nonchalant about it.

Dean nodded in approval. "A classy steak joint—nice choice, Sammy boy. And I'm guessing you'll catch some chick flick? All things considered, you still got the moves, kiddo. What time are you picking her up?"

"In about... ," he glanced at his watch. "Crap, in like 40 minutes." He quickly stood up. "I need to get ready." He still had to shower, shave, and pick out something date-worthy. Did he even own anything like that? All he had were lame lawyer clothes as Dean called them. He shook his head, brushing away the thought. He'd figure it out. He dropped off his glass in the sink before his girl's voice drew him back in.

"Can I pick out your clothes, Daddy?" It was something he let her do every now and then when Sam knew he would be stuck inside the office all day, just in case she picked something horrendous.

"Maybe another time, peanut." It was too risky tonight.

Her little brow furrowed. "But I want to today."

There was an underlying attitude of defiance, which prompted Sam to quickly reply in a warning tone, "Emily..."

She slouched down in her seat at the scolding and mumbled quietly, "I just want to help." She was very big on being a helper around the house these days. Being a helper seemed to run in the family.

Dean cleared his throat, trying to get her attention before this storm could get any worse. "Hey Em- your dad needs to pick out his own clothes for this one, okay? We can watch a movie instead of picking out boring clothes."

But all Emily could hear was that she couldn't do what she wanted, even with the mention of a movie. Her face became a defiant pout. "But I want to help!"

Sam's voice turned stern. "Emily, I said you can help another time, just not today, okay?"

Her eyes filled with tears. "No! Not okay!"

Sam reached down and picked her up, placing her effortlessly on his hip. He gave her a touch of The Eye and leaned in so she could hear. "This is your last warning before I take you to a time out."

Her brow furrowed again, clearly not liking what he said but she rested her head on his shoulder and didn't say a word. Sam looked at Dean with an apologetic smile. He explained, "Somebody was too excited today to take a decent nap." Emily couldn't wait for Uncle Dean to come and had refused to sleep in case she missed his arrival, no matter how much Sam had assured her that she wouldn't miss a moment. Sam knew this was going to make things much harder for his brother - a grumpy and tired four year old wasn't an easy feat for even the most veteran parents. It wasn't long for the parental guilt to settle in.

Dean's eyes widened a bit- he knew that Emily could get pretty cranky if she missed her nap. He suddenly got just a touch nervous, but like hell he'd show that in front of Sam. He walked over to the two of them and held out his arms for her. "Do you want me to take her so you can get ready?"

Sam felt his anxiety start to ease slightly at Dean not freaking out over the lack of nap. The father started to lean toward Dean to hand her off but he could feel her clinging to him for dear life. Sam let out a long breath and then tried to sound overly excited. "Hey, why don't you help show Uncle Dean where the movies are? I bet he needs help picking out the right princess one. He doesn't know them as well as you do." He bounced her a few times, trying to instill some excitement.

Her brows rose and she looked over at Dean, waiting to see if he really did need help or if it was a trick. Her skeptical look was definitely one that she had inherited from her mom.

Dean instantly threw on his best excited face. Hopefully, Emily wouldn't take after her father and know that Dean was going to lie through his teeth. "Yeah! Princesses! Awesome! I'd probably mess it up trying to figure out which one it is you want. You want to show me which one we're watching?" He held his hands out to her, palms up, as an invitation to come to him.

She slowly lifted her head up and sighed, accepting the burden to help. "It's okay, Uncle De." She reached over and climbed into his arms. "There's lots of princesses so it's hard to learn. I can teach you though." Dean slightly turned to the side so Sam was out of her eyesight. Sam threw him a thankful smile and disappeared up the steps to go shower.

"Alright. We got a plan. Let's go see what princess is the right one." He was careful to keep her turned away from the stairs until they got into the living room, where he stopped in front of the DVDs. "So, kid. Which one is it?"

She expertly pulled out a movie and showed it to Dean. "This is Ariel. She lives under the sea." She sat it down beside her, face up to Dean could see. She grabbed another. "This is Pocahontas. She's a Native American princess!"

"So which one is this?" He picked up Beauty and the Beast.

She gasped in awe. "That's Beauty and the Beast! Belle is a pretty pretty princess and then the beast is like this big big beast but he's really a prince!"

He blinked at it a couple times. "Huh. A beast. Now that's cool. Okay- so...which one is Aladdin?" He was about to throw up from all the pixie dust around.

When Uncle Dean called something cool, Emily immediately reconsidered which movie she had wanted to choose. "We can watch the Beauty and the Beast! They gots talking forks and a tea pot!"

"Talking...forks." And he thought he'd seen some weird stuff... "Okay. Do you want to watch that instead of Aladdin then?"

Her eyes went wide, like he had just asked her the toughest question ever. She reached over and picked up the Aladdin movie. "But I love them both, Uncle Dean. I can't pick."

"You ever heard of the 'eeny meany miny moe' method?"

She grabbed both movies, one in each hand and stood up. "No! I don't want that. I want Daddy to pick." She headed for the stairs.

"Whoa there, kid." He jogged after her, picking her up and heading back into the living room. "We need to leave your dad alone right now. He's getting de-stinkified."

However, she was not having it. She held her arms straight up, trying to slide out of his grasp like liquid. "No! I wanna ask Daddy now!" It was not that she cared to see her dad but it was that she was being told "no" and in her tired mind, it was enough to tip her emotions over the edge.

Dean was thrown for a loop. He fumbled, but regained his grasp on her, terrified that he was going to drop her. "Well...you can't ask your dad now, kid. So...quit squirming." He tightened his grip on her in case she decided to make a break for it again.

She squirmed even more, trying to break free and started to whimper like she was on the verge of either yelling or bursting out crying. "But I want toooooo. I wanna ask Daddy." She continued to squirm.

Dean bounced her a couple times, like when she was a baby and would start fussing. He desperately tried to distract her- he was so not used to her behaving like this. She rarely acted out when he'd been around. "Well, if you ask Daddy, then I guess we can't play our super cool Deciding Game. That's too bad- it's really fun, and I wanted to play it with you." He knew that he was laying it on thick, but he didn't know what it would take. He didn't loosen his grip on her at all.

She instantly stopped squirming when she heard "cool" game. She looked up at him and repeated with some caution as if to show that if she didn't like his answer, the fussing and squirming would resume. "What cool game?"

Dean shrugged theatrically. "Well, since you wanted to bug your dad instead of staying with me, I guess it doesn't matter, does it? Unless...do you want to stay with me and learn the cool game?"

She fidgeted for a moment as she internally had a battle: stay and learn the cool game or go see her dad like she wanted to do but wasn't allowed. The struggle flashed across her face and she finally answered, "I play the cool game."

"Are you sure? 'Cause it's a really cool game. And I don't just do it with anyone."

"I wanna do it," she confirmed. "Please!" she added with a big grin.

Ever so gently, Dean walked back into the living room and sat down on the couch. He took the movies and placed them on the coffee table in front of them. Picking up Emily's hand, he used it as a pointing stick, going from one movie to the other as he went through the whole 'eeny meany miny moe' chant until their hands landed on Beauty and the Beast. "The big hairy monster wins," Dean explained.

She stared at the movie and then turned to her uncle. Then without a second of warning, her eyes watered up and tears spilled over as she started to cry. "But but but..." She couldn't even get words out as the tears came.

Dean was completely thrown at her tears. "Wh-wait...hey- don't cry! What's the matter? Why are you crying?" He panicked, trying to figure out if she got hurt or something. He looked around desperately for Sam, but remembered he was upstairs, and got even more worried.

Through the tears, she managed to get out "Daddy." Her tired and grumpy pre-school mind didn't like the result of their game, and the only way she could think to express her displeasure was to cry and ask for her dad.

Meanwhile upstairs, Sam's hearing that was once trained to hear even the snap of a twig was now finely tuned to hear his daughter from a distance. He didn't miss the tears and could make out the mumbling of his name. He quickly threw on a white undershirt and his jeans before taking off barefoot down the steps, needing to know if she was okay.

"Oh- uh- okay- well, your dad." Dean stretched out his arms around her on his lap to try to comfort her, when he saw Sam coming down the stairs. He quickly felt the need to explain why Emily was bawling, even though he really didn't have a clue himself. "Sam! I don't know what happened! She just- we were playing a game and- and then- this-." Dean gestured helplessly to her tears, a panicked look on his face, feeling incredibly guilty for what he apparently did. Dean was so rarely around kids that he wasn't able to interpret all the hidden meanings yet.

Sam quickly scooped her up into his arms. Her cries started to slow into sniffles as she rested her head on his shoulder. Sam leaned back, trying to get a look at her face. "What happened, Em?"

There was silence as her cries subsided and she soaked up being in his arms. She snuggled in even closer to him, if that was possible, and mumbled softly, "Uncle Dean is mean."

To be continued...