AN: So...this is my summer story. It was supposed to be a oneshot. It is not. Single parent!Ruby/Single parent!Dean has been on my to-do list for about three years so when I was finally presented with the opportunity to do this story, I got a little carried away.

Just a little note before we begin:

I'm Canadian, so I don't know much about the school system in the states. I tried to do as much research as I could, but unfortunately research can only do so much. Namely the main issue I'm having is the kindergarten cut off date. The kindergarten cut off date is basically a law that states 'if your kid isn't five by this date, sorry! S/He'll have to wait until next year.' For example, the cut off date for where I went to school (in Canada) was December 1st so I made the cut. I was able to start kindergarten while I was four in September and then turned five in October. Every state and province is different and I had a hard time nailing down the cut off date for Kansas. It seemed like every site I went to had a different answer for me. One site said if the child didn't turn five by October 16th they had to wait a year (that one works out perfectly because Ben and Evan turn five on October 11th and 15th respectively) another said August 31st and yet another said December 31st. So...I'm not sure if this story will even be technically factually correct in some places. However, apparently, if your child has been deemed too young (like...what if they turned five October 17th and the cut off date is the 16th) you can take it up with the school board. If it is in fact illegal in Kansas to enroll a four year old in Kindergarten...let's pretend they took it up with the school board, okay?

Title of chapter one from the song ''Home'' by Edward Sharpe & The Magnetic Zeroes.

Title: you're my playground love
Summary: AU, All Human: Dean Winchester and Ruby Connors strike up a friendship while trying to navigate their way through the rough, murky waters of single parenthood.
Pairing: Dean/Ruby. With minor mentions of past Dean/Lisa and past Ruby/OMC.
Character: Mainly Ruby, Dean, Lisa, Ben, Evan (OMC), and Annabelle (OFC) with some Sam and probably some mentions of John, Mary, Veronica Winchester (OFC little sis for the boys) and various OC's created for Ruby's past.
Genre: Romance/Family
Rating: K+
Timeline: Over the course of a few years. It's AU so it doesn't take place any time in the show. I think it goes from about 2004 to 2010.
Spoilers: ...I think if you know about Ben and Lisa and the fact that they exist then you're probably good.
Warnings: Um, all I can think to warn for is a few cuss words here and there. This story is, as mentioned above, all human and all AU, however. If that's not your thing, you should moonwalk out of here while you still can.
Dedication: This one is going out to ParaCaerOuVoar (otherwise known as Cantati) who is pretty much just awesomecakes. I was going to dedicate an angsty fic to you because I know you love angst as much as I do...but then this happened. Have some comedic fluff instead! Cheers, Rachy!
Notes: Title from the song Playground Love by Air. Amazing song, by the way.

Disclaimer: I do not own anything.

you're my playground love

Written by Becks Rylynn

Part One: Kindergarten

you're the apple of my eye

Rapunzel: Who are you, and how did you find me?
Flynn Rider: I know not who you are, nor how I came to find you, but may I just say... Hi. How ya doin'?
- Tangled (2010)

September, 2004:

''Mommy,'' the small boy's wide, fearful blue eyes stared up at the large school building looming in front of him in something akin to horror. ''Do I have to go? Can't I just stay home with you?'' His voice shook with fear and when his nervous eyes scanned the courtyard and caught sight of some other kids running around wildly, he paled.

His mother, busy trying to juggle both his baby sister and the diaper bag while simultaneously readjusting his backpack, glanced up at him with what she hoped was at least a semi reassuring smile. ''Afraid not, sweetie.'' She carefully smoothed down her son's shirt before reaching out to straighten his glasses. ''It's not going to be so bad,'' she promised, standing straight. When six month old Annabelle whimpered and blinked open her bleary eyes, her mother rubbed her back gently. ''I'm sure you'll have a good time, Evan,'' she said quietly. ''You'll make friends, you'll play games. I'll bet you won't even want to come home when the day's over. Kindergarten's a breeze, kid. Just don't stress over it.''

Ruby Connors wasn't going to lie. She was probably more anxious about her son's first day of school than he was. He was a smart little boy and she had no doubt he'd flourish if he could get over his fears. It was just that he was small for his age, he had asthma, and he was painfully shy. These were all things that made her a little paranoid. She hated that she wouldn't be there to protect him. And it wasn't just that she wanted to protect him from all the things that scared him about the idea of school. She was all too aware that sometimes people had a nasty habit of focusing their judgment on her family and the fact that maybe she was a little younger than some of the other mothers.

She had packed up her life (and her children's lives) and moved all the way from Wilmington, North Carolina to Lawrence, Kansas because she wanted to get away from the disdainful looks and the passive aggressive comments about her age. She had since come to realize those little looks were going to follow her around wherever she went. Well, that was fine. People could judge her all they wanted, but she would not allow them to judge her kids.

Yes, she had her first child at eighteen. No, that did not make her a whore or an unfit mother.

Why was that lost on so many people?

''I want to stay home with you and Annie,'' Evan whined, stomping his foot for emphasis.

''I know you do, babe,'' she sighed, ruffling his hair. ''But please just give it a chance, okay? For me?''

He swallowed, eyes darting around in fright once again. ''Okay.''

She smiled triumphantly, letting out a breath. ''Good. All right, now, you've got your glasses, your back up glasses because you go through glasses like socks, your inhaler, and your snack. Did we forget anything?''


She pinched her lips together. ''I thought you were going to let your sister look after Teddy for today?''

''Well...'' He folded his arms crisply. ''I don't think she's doing a very good job. Look at her. She's sleeping on the job. And where is Teddy? Maybe we should skip this and go home so I can look after Teddy the right way.''

When he tried to move past her, she grasped the back of his jacket and pulled him back. ''Nice try. But Teddy's sleeping in the car. He was tired. Teddy was up all night worrying about today, remember?''

''You should talk to him about that,'' Evan said slowly, biting down on his bottom lip.

''Only if you remember to keep your inhaler with you in your pocket at all times.''

He nodded. ''Deal.''

When the sound of a child screaming in excitement echoed through the air, Annabelle made another noise of displeasure and Evan tightened his lips. Ruby frowned at the sight of the worry on his face. Four year olds should not worry as much as her son did. He was a major stress case. Admittedly, she was about ninety eight percent certain it was something he had, unfortunately, gotten from her. ''Hey,'' she gave him a bright smile, nudging his shoulder slightly. ''Remember what we talked about? You said you'd be brave today. You're my big guy now, right?''

''Right.'' He tried his very best to display a confident smile for his mother, looking incredibly relieved when it only shook a little. ''Brave like a lion.''

''Brave like a superhero,'' she corrected, grazing her fingers over his cheek.

''Like Batman?''

''Just like Batman,'' she winked, holding out her hand. ''So, what do you say, Batman? You ready to rock and roll?''

Evan took a deep breath and clutched at the straps of his backpack. ''I guess so.'' He let out a long slow breath and grasped his mother's warm, safe hand. ''Okay,'' he said bravely, holding her hand tighter. ''Let's go.''

Daisy: What kind of garden do you come from?
Alice: Oh, I don't come from any garden.
Daisy: Do you suppose she's a wildflower?
- Alice in Wonderland (1951)

''Wow!'' The boy twirled in the cold morning sun, staring up at the school building with wonder and excitement dancing in his eyes. ''It's so big! It's! Was it always giant?'' Energized to the extreme, he twirled again. Then he promptly decided that he did not have the patience to be bogged down by his unsuitably heavy backpack and threw it at his father.

''Jesus,'' was the exasperated response from his father. ''What the fuck's in this thing?''

''Dean,'' Lisa Braeden hissed, tossing her dark hair over her shoulder. ''We're in a school yard.''

''Really? 'Cause I thought we had just stumbled into munchkin land. Does this mean we're not going to be serenaded by the lollipop guild.''

What he thought was a clever and witty response, only got him a dry, narrowed eyed look instead. ''Just tone down the swearing.''

''Dad!'' A few steps ahead of them, eyes still comically wide, their bouncing four year old - literally. He was hopping up and down like a little bunny rabbit on crack - turned to face them, spreading his arms wide. ''Look how huge this place is!'' He spun around on his heel to stare at the school, grin spreading across his lips. ''When's the bell ring? Do we get to play outside? Is there food? What about girls? Will there be - ah!'' Two strong arms lifted him off the ground quite suddenly, bringing him up to eye level with his dad.

''Ben,'' he drawled slowly. ''Are you high?''

''No!'' The boy all but squealed, squirming in his father's tight grasp. ''I'm excited! Put me down now please. I wanna run. I feel like running.''

''Maybe I shouldn't have let him put syrup, whip cream and chocolate sauce on his waffles this morning,'' his mother mused thoughtfully with a sheepish looking smile.

Dean Winchester somewhat reluctantly lowered his hyperactive son to the ground, arching an eyebrow when Ben's immediate reaction was to start running in circles. The kid was a menace. He was going to raise hell in this school. Dean honestly wasn't sure if he was supposed to be proud or kind of terrified.

Ben ran ahead of his parents like a miniature rocket, stopping only to throw an impatient sounding, ''Come on already!'' over his shoulder.

Dean chuckled under his breath. He wasn't at all worried about his son. Ben made friends faster than any kid Dean had ever met and he wasn't one to get shy. Ever. Dean was more concerned about the other kids. And the poor teacher. His worries weren't exactly unfounded. He loved his son, but Ben was a handful. He was all coiled energy and sugar rushes. He was like a bull in a china shop. He was spirited. Lisa had always told him that the mildly insane parts of Ben undoubtedly came from his Winchester genes. ...Yep. Definite possibility.

The sound of sniffling brought Dean's attention back to Lisa. For what seemed like the millionth time that morning, her eyes were glimmering with tears and she was digging around in her purse for a tissue. ''For Christ's sake, Lise,'' he muttered, shaking his head. ''You're not gonna start that again, are you?''

''They're taking my baby!'' She wailed dramatically.


''The government! The people with the-the schools!''

Dean stared at her for a moment. ''He's just goin' to kindergarten, Lisa. It's not like he joined the Marines.''

''It's just...'' She shook her head, wiping at her eyes. ''Do you remember the day he was born?''

He sighed heavily, shooting her a look. ''Hard to forget. You broke two of my fingers.''

''It seems like it was just yesterday,'' she blubbered. ''And...And he's so little! What if he doesn't make friends? What if he needs me? I'm his mother! I think we should wait another year. I-I mean, he's just a baby!''

''Lisa.'' Dean calmly put his hands on her shoulders, steering her towards the elementary school. ''We've talked about this. We both agreed he's ready. He's agreed he's ready.''

''But - ''

''He's going to be fine. He's going to make friends. He's going to terrify the teacher with his energy... It's all good.'' He slung Ben's Thomas the Tank Engine backpack over his shoulder and wrapped his arm around her shoulder when she began to slow down as if she were ten seconds away from digging her heels into the ground and refusing to move. ''He's going to be five in October. He's not a baby anymore, Lisa, and this is what he wants. He's been waiting for this all summer.''

''But what if he gets his hopes all up and then he's disappointed?'' She questioned meekly, toying with the Kleenex in her hand until it was almost nothing more than mulch.

''Well, that would be called life,'' he said reasonably. Wow. It was mind boggling when he was the logical member of this parenting team. Usually she was the calm and collected one and he was the one who wouldn't let Ben play with marbles because marbles went places. ''Seriously,'' he told her, ''you need to buck up, Braeden.''

In response, she pulled away from him to blow her nose noisily. And then she shot him a withering glare. ''Screw off, Winchester. I'm allowed to be nostalgic. My baby's growing up.''

Dean squinted against the bright sunlight, looking ahead of them to where Ben was currently twirling around the flagpole. ''At least bring it down a level. You're embarrassing the boy.''

''...He doesn't seem embarrassed.''

''Okay, well, I'm embarrassed. You need to calm down, Lisa,'' he advised. ''Think - ''

''About something else?'' Lisa interrupted. She pursed her lips, stopped in her tracks to stare at him for a moment and then nodded. ''Okay. Can do. Let's talk about your love life instead. I think you need a girlfriend. Then maybe you'd stop hanging around me so much. It would be peaceful. Still wanna talk about something else?''

Ah, yes. The love life topic. He would never understand how she managed to bring up the topic of his - at the moment completely inactive - love life in every conversation they had. It was freaky. It frightened him. For your information, yes, he was single. And no, that did not mean he was an unbearably unhappy, lonely, sad, pathetic man. It just meant he was choosing not to be in a relationship at the current time. Thankfully, that was the moment Ben stopped twirling around the flagpole and made the choice to try and climb it instead, effectively saving his dad from an uncomfortable relationship talk. Well, thank God for his spirited son. ''You know, I'd really love to talk to you about this, Lisa. Really, I would. But as it turns out,'' he gestured towards Ben. ''Our son is, apparently, becoming a monkey so I'm gonna go pry him from the flagpole.''

''Yeah,'' she smirked, folding her arms. ''Am I embarrassing you now?''

''You're crazy,'' Dean threw back lazily before he spun on his heel and started towards Ben.

''You know,'' she called after him. ''That backpack makes you look real manly.''

''Oh, you wish you could rock Thomas like I can!''

Prince Eric: Believe me, Grim, when I find the right girl, I'll know. Without a doubt, it'll just - bam! - hit me. Like lightning.
- The Little Mermaid (1989)

Ruby quietly bounced Annabelle in her arms, trying to shush her daughter and keep her eyes on her son at the same time. It was extraordinarily clear that Evan was not in his element at the moment. He was side stepping the other kids and the toys and he kept sending her pleading looks. She likened it to something like torture. He obviously didn't want to be there. But what else was she supposed to do? He was going to be five in October. People - namely her father - kept telling her she couldn't keep coddling him.

She couldn't keep him out of school if she wanted to. Her job started in a week and she still had to find a babysitter or an acceptable daycare for Annabelle. It wasn't like she had anyone to help her either. Her parents didn't ''agree with her choices'', her sister was a wackjob, and the last she heard, her ex-husband was somewhere in Texas with his new fiancée. It was pretty much just her and the kids right now. As terrifying as it was, she had to make Lawrence work. Evan had to go to school, she had to go to work, Annabelle had to not scare off whatever babysitter was brave enough to take the job and they all had to adjust.

His teacher had informed her that she could stay as long as she wanted. According to the teacher, lots of parents did. It was a tempting offer, but Annabelle was tired, fussy, and most likely hungry and Ruby knew that if she stayed for too long, she'd never be able to leave. She waited until Evan stopped shooting big Bambi eyed looks in her direction and when he looked at least half comfortable, as far away from the rambunctious dark haired little boy as possible, she slipped out the door.

Just in time for Annabelle to lose all patience and let out a wail. As the door to the classroom clicked shut and Annabelle started to cry, the parents lingering in the hallway turned to look at her. She grimaced, rubbing the baby's back. ''I know, baby. I know you're hungry.'' She hesitated, glancing behind her towards Evan's classroom. ...Well, he hadn't run out of the room screaming, crying and trying to climb up her leg. That had to be a good sign. She wanted to wait a few more minutes to make sure he was all right, but the looks being thrown in her direction told her Annabelle's crying was beginning to grate on people's nerves.

All right then. Time to go.

Ruby sighed and shifted her daughter into a better position. Unfortunately for her, moving Annabelle caused the diaper bag haphazardly slung over her shoulder to slip off her shoulder and fall to the ground. Great. Just her luck. She was beginning to think she was cursed. Could nothing ever be easy? She bit back a curse, but before she could attempt to retrieve it, someone else swooped in and swept the bag from the floor. She looked up at her savior, took in the extremely handsome man before her, and took possibly a moment too long to respond. ''...Thanks.'' Well, hey. In her defense, most fathers she had encountered did not look like him. His general appearance was astonishingly aesthetically pleasing. If you wanted to get technical.

''Sure.'' He offered her an easy smile, which only managed to make him more attractive.

In return, she gave him a smile that she desperately hoped didn't look as tired as she felt. Annabelle's supersonic wails had died down into frustrated whines, but she was wriggling and squirming enough to let Ruby know that A) somebody needed to get food in this baby before she unleashed the rest of her tiny fury onto the world, and B) she did not appreciate being held prisoner in her mother's arms.

''She's not a morning person?'' He guessed, reaching out to place a hand on Annabelle's back when the baby jerked and tried to throw herself out of the safety of her mom's arms.

''Not really,'' Ruby said breathlessly, running a hand over her daughter's head. ''She must get that from me. All my kids seem to get from me are my negative traits.''

''Well, she has your eyes,'' he told her simply. ''I can't imagine that being a negative trait. You have beautiful eyes.''

She narrowed said beautiful eyes, but couldn't quite keep a small, amused smile from washing over her lips. ''Are you trying to flirt with me?''

He smirked, leaning in just a little bit closer. ''Would it be a problem if I was?''

She flicked her eyes to the pretty young dark haired woman he had come with, flipping her phone shut. She recognized them as the parents of the overly hyper boy Evan had been utterly terrified of. ''Dude,'' she deadpanned. ''Your wife is right - ''

''Oh, we're not married,'' the woman said, jumping in between them with a bright, cheery smile. ''Not even close. We just procreated because he's pretty and I'm smart and we felt that blessing the world with a child made from our genes could create world peace. But in general, I sort of find him unbearable. Trust me, sister, you can have him. Although, I do have to warn you - ''


She frowned impishly, peering up at him. ''Oh, I'm sorry you don't appreciate me airing your faults to the pretty girl? My bad. Good luck then! I'm going to call your mom and tell her you've got a new girlfriend.'' Still beaming, she patted his arm, winked at Ruby and brushed past him.

Lips parted in surprise, he slowly turned his attention back to Ruby, who was having a hell of a time keeping her laughter in. ''She's kidding,'' he eventually said after a moment of opening and closing his mouth uselessly. ''...I don't have any faults.''

Ruby raised an eyebrow and slipped the diaper bag over her other shoulder, shifting Annabelle to her other hip. ''Thinking you don't have any faults is a pretty big fault.''

He shrugged. ''In time, you'll learn to find my arrogance charming.''

''Oh, I will?''

''Yes. Definitely.''

''In all seriousness,'' she began, untangling Annabelle's small hand from her hair. ''You took a big chance with me. You don't even know if I'm married or not.''

''Are you?''


''Then it doesn't matter,'' he decided. ''If I come across someone who looks like you, I'm going to take that chance.''

''You're trying to make me blush.''

''Is it workin'?''

She laughed softly and looked away, hoping he couldn't see that his ploy was working just fine. When she looked back at him, he was offering her his hand, and for reasons incredibly unknown to her, she felt compelled to take it. ''I'm Dean.''

She hesitated a moment. Okay, so she didn't have the best track record with guys. There was Travis, and then there was... Well, all right, so that completed her track record. But it was bad. He messed her up really bad in the whole relationship department. But, she told herself, that didn't particularly matter. This was just a tiny little minor flirting incident. What were the chances of it turning into some storybook or movie like romance? She accepted his hand with a softer smile, met his eyes, and tried to ignore the strange electric charge. ''I'm Ruby.''

Macaulay Connor: It can't be anything like love, can it?
Tracy Lord: No, no, it can't be.
Macaulay Connor: Would it be inconvenient?
Tracy Lord: Terribly.
- The Philadelphia Story (1940)

Ruby quietly shut the door to Annabelle's nursery, baby monitor held in her hand. Finally, the little girl was asleep. Annabelle was, to put it lightly, a demanding baby. Evan had been very relaxed and low maintenance as an infant. Very zen. Everyone had told her to count her lucky stars. Annabelle on the other hand, was not zen at all. She had a terrible habit of waking up when someone tried to leave the room. She'd fall asleep and just as Ruby was trying to tip toe out of the room, she'd wake up and scream bloody murder. It was beyond exhausting

Stifling a yawn, Ruby weaved around the scattered yet to be unpacked boxes in the hallway, reaching up to free her hair from the sloppy ponytail it was in. She should probably unpack those boxes and get some work done tonight while the kids were sleeping. ...Or she could sleep. Yes, that sounded like more fun. Definitely. Today had been trying. She thought she deserved some rest.

She paused in front of Evan's room and quietly peeked her head in to see if he was asleep. He wasn't. Lying flat on his back, fingers digging into his teddy bear, Evan was staring intently at his ceiling and frowning deeply. Ruby knocked on the door, smiling softly when he turned his eye to her. ''Hi, sugarbug.'' When he didn't respond to the familiar nickname, she closed her eyes briefly and took a deep breath. She tip toed across the cold wood floor and slipped into his bed next to him, putting the baby monitor on the bedside table. He sighed heavily and went back to staring at the ceiling. She licked her lips and sunk farther down under the covers, looking up at the ceiling with him. ''You know what we should do this weekend?'' She whispered. ''We should put up those glow in the dark stars we bought.''

He shrugged, lowering his eyes to his bear.

She swallowed a sigh, and tried to keep her smile on her lips. ''Hey, you never really told me about your first day of school. Was it as bad as you thought it would be?''

He tensed, clutched his bear tightly to his chest and sent her an unhappy, wide eyed look. Slowly, unable to meet her eyes, he nodded. ''Yes,'' he rasped out. ''It was. It was really, really, really bad, Mommy.''

That was one sigh she couldn't quite swallow. ''Evan...''

''T-They're all too loud and messy. And it's boring. And...And...I hate Ben Winchester!''

''Who's Ben Winchester?''

He scrunched his nose up in disgust. ''He's loud and messy and rude and bouncy and weird and he talks a lot and he makes me nervous a-and then I have to use my inhaler - ''

''Okay,'' she cut in. ''You're not a fan. But, honey,'' she brushed blonde hair out of Evan's face. ''He's just one boy.''

''One really weird boy,'' Evan sulked. ''He's ob...ob...obo...What is it?''



She laughed and wrapped her arm around him. ''Evan - ''

''And I want to be with you,'' he went on, pushing himself into a sitting position. ''I don't want to go to school. I want to stay home with you and Annabelle and Teddy.'' He looked down at his teddy bear, stroking its fur with care. ''I think Teddy missed me today,'' he mumbled unhappily. ''I bet he was sad. Do you want to make Teddy sad?''

''Of course I don't want to make Teddy sad.'' Ruby reached out to run her hand over the well worn (well hugged) teddy bear in her son's hand. ''But do you want to know what I think?'' When he didn't answer, she snuggled closer to him, running her fingers through his hair. ''I think Teddy will get used to you being gone. I think that he'll start making friends with your other toys and I think they'll have great adventures during the day. He'll always be glad to see you, but eventually, Evan, Teddy won't be sad anymore. He'll have lots of fun during the day with his new friends, and then when you come home after school, he can have adventures with you. Doesn't that sound like a well rounded life? Doesn't that sound like fun?''

''But what if he doesn't have fun? What if he never makes friends?''

''He will.''

''What if he doesn't?''

''Then at least he will always have you.''

''What if he just spends his days all sad and stuff waiting for me to come home?''

''Then he'll just have to find a way to get through the days and know that it's all going to be all right, because at the end of the day, you're always going to come home to him.''


''Yes, baby?''

''Are we still talking about Teddy?''

''No, sugarbug.''

Evan let out a long breath and laid back down, biting his lip and holding his bear close. ''I'm going to have to go back to school, aren't I?''

''I'm afraid so.'' She winced when she saw the distress written on his face. Part of her wanted to pull him out of kindergarten just so she could see his smile again, but the other part of her knew that he could do this. He could. He was a brilliant little boy and maybe it took him a little longer to get used to change, but eventually he would. She knew he was scared and she knew that all of this change - school, the move, the new house, the complete lack of a male presence in his life - was tough on him, but she also knew that he was stronger and braver than he looked. She had nothing but faith in her son. She knew that if they could just get through these first few months, he would be fine. He would. She had to believe that. ''Tell you what,'' she started. ''How about you go to kindergarten for a month and if things haven't gotten better after a month, we'll re-evaluate. How does that sound?''

He cleared his throat, playing with the ears of his bear. ''A month?''

''One month.''

''Then...okay. I...I guess I'll go.''

''That's my guy.'' She leaned forwards to wrap her arms around him, enveloping him in a hug. ''You can do it, you know,'' she whispered in his ear. ''I know you can.''

''Do what?'' Evan asked.

''Make friends,'' she said. ''Have fun.''

''You think so?''

She pulled back, cupping his cheek gently. ''Definitely. Now,'' she leaned in to press a kiss to his forehead. ''You should probably get some sleep, okay, buddy? It's getting late.''

For the first time that day, she saw a real, genuinely excited smile cross his lips. It was only for a moment, but it was there. He looked away from her before she could see it light up his eyes, reaching over the side of his bed to pluck a book from the floor. ''Fine, but before you go,'' he handed the book over to her. ''You have to read me a book.''

She looked down at the book, smile threatening to break out over her lips. ''This one again? Evan, don't you ever get tired of this book?''

He blinked up at her owlishly, looking like he genuinely didn't understand the words coming out of her mouth. ''No,'' he said flatly. ''Why would I get tired of this book? It's awesome.''

''All right then. You ready?''

Evan pulled Teddy closer and curled into his mother's side. ''Ready.''

Out of the corner of her eye, Ruby looked at her son, waiting patiently for his story to be read, and smiled. For a brief moment for the millionth time, she wondered how time managed to go by so fast, and then she shook her head, and started to read. ''The news just came in from the County of Keck, that a very small bug by the name of Van Vleck is yawning so wide you can look down his neck. This may not seem very important, I know. But it is. So I'm bothering telling you so.''

''The yawn of that one little bug is still spreading! According to latest reports, it is heading across the wide fields, through the sleepy night air, across the whole country toward every-which-where. And people are gradually starting to say, ''I feel rather drowsy. I've had quite a day.''
- Dr. Seuss, The Sleep Book (1962)

There were times - few and far between, you must understand - when Dean couldn't help but think things would be easier if he and Lisa were together. Things would be easier if he had someone to help him all the time, things would be easier if he and Lisa could give Ben something more stable than what they had, things would be a lot easier if they had had Ben when they were a little older and a little wiser. But life didn't work out that way. Life worked out this way, and it was the Winchester way to take what they were given and make the best out of it. That was all anyone could do, really.

Lisa was a good mother, and a good girl. She was a good woman. Dean didn't have full custody because she was an unfit mother. He didn't feel alone because she didn't have her shit together. In reality, they both pretty much got their shit together the moment Ben came screaming into the world. It was what they had to do. Dean had full custody because Lisa was an overachiever. She worked long hours all week, she went on a lot of business trips, and she didn't have a backyard. She wanted Ben to have a backyard. She was very adamant about that. So, when Ben was two, Dean was granted full custody because he had the big house with the big backyard and that was what Dean and Lisa wanted to give their son. Most of the time it worked out. Lisa spent more time at Dean's house than she did at her own and it wasn't like Ben was losing out on a relationship with his mother because he wasn't. He had a fantastic relationship with his mother.

But there were moments. Just fleeting little moments where Dean would think it would be easier if he and Lisa still felt that way about each other. It wasn't a reality. It wasn't ever going to be a reality. They were together exactly one year and nine months before they decided they didn't really work as a couple. All they were ever going to be was friends. They were both fine with that. It was just that...well...

Most of those fleeting little moments? Yeah, they came at bedtime.

Sometimes Dean really wished he didn't always have to be the one to wrangle Ben into bed. It truly was a daunting task. He wasn't even exaggerating a little bit. Ben hated bedtime and often came up with wacky but creative ways to attempt to get out of going to bed. It had always been that way. For the first two years of his life, he hardly spent a night alone in his room, and then when he finally did start spending the nights in his own bed, he'd hide at bedtime because he hated going to sleep. He hated to miss things. It was understandable for a four (almost five) year old. But it was fucking annoying.

Tonight, despite the fact that the boy must have been at least a little tuckered out from his first day of school, was no different.

When Dean poked his head into his son's room to tell Ben to start getting ready for bed, he was expecting to see the little boy playing with his toy cars like he did every night. Instead, he was greeted with the sight of an empty bedroom, toys strewn out all over the floor. ''Ben?'' He whirled around, stomping out into the hall and leaning over the banister. ''Ben!'' First there was the breathtaking moment of heart wrenching panic. Then there was the brief second of frustration because sometimes the largeness of this house had disadvantages, such as when he was searching for his tiny little son who liked to hide in odd places. But then a very familiar giggle floated through the air from behind him.

Dean let out a breath, pinching the bridge of his nose. Oh, yeah. That was fine. Just give him a second to jump start his heart. He sagged against Ben's doorframe, eyes trained on the boy's bed. ''Ben...''

''Ben's not here,'' a small voice responded ominously.

''It's really shocking that Ben decided to disappear at bedtime,'' Dean mused, pushing off the wall. ''Because that never happens.'' He expertly dodged the five thousand million toys on the floor and leapt onto Ben's bed, pulling out a stuffed dog from underneath him. ''I guess I'll just have to - ''

The door to Ben's closet burst open and the little boy raced out, hollering something about a ''closet monster attack'' at the top of his lungs, right before he threw himself onto top of Dean with a wild battle cry. ''Son of a bitch!'' Dean cried out, catching Ben before he could fall off the bed. ''Closet monsters are real!''

''Told you!'' Ben paused for a moment and then grinned that mischievous little grin of his, waggling his fingers mysteriously. ''And the only way to stop them is to...feed them ice cream.''

''Ice cream, huh?''

''Chocolate ice cream.''

Dean clicked his tongue with a shake of his head. ''Sorry, closet monster. We don't eat ice cream at bedtime around these parts. Those are the rules.''

''...Closet monster doesn't approve of those rules.''

''Too bad closet monsters aren't in charge.'' Dean slipped off the bed, leaning down to pick up a few scattered toys.

As expected, Ben pouted for about a minute and a half, and then moved onto his next get out of bedtime scheme. ''Hey, Dad, you wanna hear about my day?''

''I've already heard about your day,'' Dean said, depositing an armload of toys into the toy chest in the corner. ''Numerous times.'' He picked up a few books from the floor and carefully set them back on the bookshelf. ''By the way, kid, you have really got to start picking up your crap.''

Tongue between his teeth, Ben pushed himself onto his knees, staring up at his father with a frown. ''Mom says you're not supposed to swear around me,'' he pointed out, waving a disapproving finger at his father.

''Do you repeat what I say?''


''Then free speech still exists. And you do need to pick up your crap. That's just a fact. Look at this place. It looks like a tornado hit.''

''Maybe I like it like this,'' Ben responded hotly.

Allowing a small huff of laughter to escape his lips, Dean scooped up his son without warning and threw him over his shoulder, ignoring the startled shriek he got in return. ''When I was your age,'' he started, carrying his giggling son out of the room. ''My room was always clean. ...Of course that could have something to do with the fact that after Veronica was born, I had to share a room with little neat freak Sammy, but still.''

''Where are we going?'' Ben screeched through peals of laughter. ''Are you going to throw me in the dungeon? Because I'm not really a closet monster, I swear!''

''It's teeth brushing time, bud.''

''But - ''


''But - ''

''Still no.''

''I am not happy!''

''I'm okay with that.'' Kicking open the bathroom door, Dean placed Ben on the counter, handed him his toothbrush and stood in front of the door with his arms crossed while Ben stared at him, looking wholly unimpressed. Ben's eyes curiously studied the small opening beside Dean that could potentially allow him to escape so he could run and hide under his bed. Dean quickly stepped in front of it and pointed a finger at him. ''You shall not pass.''

Ben huffed, but seemed to realize that he was not going to be going anywhere because he finally snatched up the tube of toothpaste. He sighed and tried one last time to get out of bedtime by sending his father a puppy dog eyed look. When it didn't work, he sighed dramatically once more and shoved his toothbrush in his mouth. ''I hate bedtime,'' he mumbled through a mouth full of toothbrush and toothpaste. ''I bet...I bet none of my friends have to go to bed this early!''

''Less talking, more brushing.'' Dean leaned against the doorframe, tilting his head to the side curiously. ''You have friends already? I thought today was mostly spent bouncing off walls.''

''I have lots of friends,'' Ben informed him plainly.

''Impressive. You're very personable, aren't you?''

Ben stopped brushing his teeth long enough to stare blankly, then shrugged and went back to brushing his teeth. When he was finished brushing his teeth, probably a lot sooner than a dentist would recommend, he hopped off the counter and puffed his chest out proudly. ''Everybody's my friend,'' he said with a wide, toothy smile. ''Everybody's my friend and I'm their friend.'' He paused, seemed to consider this statement for a moment and then frowned and plastered a very serious look on his face. ''Except Evan. He is not my friend.'' He nodded to emphasize this point and then carefully stepped around his father.

''You seem very adamant about that,'' Dean commented.

''Evan,'' Ben stuck his nose up. ''Is a freak.''

''Hey.'' Dean scuffed his boy on the back of the head, shooting him a warning look. ''Not nice.''

''You don't know Evan.''

''I don't care. You don't call people freaks. How would you like it if someone called you a freak?''

''Well, that's not - ''

''Ben, you're a freak.''

Ben stopped in his tracks to gape up at his father, looking deeply wounded by that comment. ''What? That's so mean. Why would you say that?''

''Why would you?''

''...Okay, I don't like that.''

''I'm sure Evan didn't either.''

''Ugh, fine. I won't call him a freak.''

''Thank you. Now,'' Dean grasped Ben's arm and spun him around to face him. ''Where exactly do you think you're going?''

''To bed?''

''Nu-uh. Nice try, but you,'' he turned Ben around and steered him in the direction of his own bedroom. ''Are sleeping in your own bed. Don't whine at me,'' he added on quickly when Ben opened his mouth. ''You're a bed hogger. All right? You're a big kid now, dude. A big, annoying kid. You're going to go to school, you're going to sleep in your own bed, and tomorrow, you're going to apologize to this Evan kid for calling him a freak. I'm not raising you to be a douchebag. I'm raising you to be awesome.''

''But that's the problem!'' Ben burst out, throwing his hands up in the air. ''I am awesome! I'm awesome and he's not!''

''People are awesome in their own ways, Benjamin Isaac Winchester.'' Dean absently flicked the light switch off when he walked into Ben's room and the glow in the dark stars on the ceiling lit up in the darkness. ''You're about to spend thirteen years learning that.'' Effortlessly, he lifted Ben into his arms and chucked him onto the bed, much to the young boy's delight. ''You and me, kid?'' Dean continued, jumping onto the bed next to Ben. ''We're Winchesters. Winchester's don't bully people. What do Winchesters do?''

Ben started to roll his eyes, but luckily for him, he remembered at the last minute that perhaps that wasn't the wisest idea. ''We help people,'' he recited flawlessly.

''Exactly.'' Dean grabbed a book from the floor beside the bed and flicked through the pages. ''I'm not sayin' you have to be friends with this boy, but you're not going to make his life a living hell. You hear me?''

''Yeah, Dad.''

''Good. Now, lie down, shut up and let me read because it's way past your bedtime and you have to get up early tomorrow. You have school.''

''You're very bossy.''

''I know, I think your mother's rubbing off on me.''

Stifling a smile, Ben burrowed under the covers, tucked his stuffed dog under his arm and waited excitedly for his father to start reading.

Out of the corner of his eye, Dean glanced over at his beaming little boy and swallowed a small bark of laughter. It didn't happen very often, but every once and awhile, he really wished time could stand still. With a shake of his head, Dean pushed those thoughts out of his mind, cleared his throat and started to read. ''The news just came in from the County of Keck, that a very small bug by the name of Van Vleck is yawning so wide you can look down his neck. This may not seem very important, I know. But it is. So I'm bothering telling you so.''

''Ninety nine zillion, nine trillion and two creatures are sleeping! So... How about you? When you put out your light, then the number will be ninety nine zillion, nine trillion and three.''
- Dr. Seuss, The Sleep Book (1962)

The next morning, in Miss. Clementine's kindergarten class, Ruby Connors looked up and caught Dean Winchester's eye from across the classroom. It wasn't intentional. It was just like gravity. It was something that just happened. Completely unavoidable.


But it certainly didn't - and wouldn't - mean a thing.

What were the chances of that happening?

Allie: They fell in love, didn't they?
Noah: Yes, they did.
- The Notebook (2004)

end part one

AN: By the way, the story Dean and Ruby were reading their kids was - in case you didn't get this - The Sleep Book by Dr. Seuss. And yes, it is, in fact, awesome. Also: Who else hates the changes they're making to the site? I'm totally not down with change.

Just a little warning before I end this chapter: Usually my summer stories are updated pretty quickly. This one probably won't be. It'll be finished sometime before July 24th (or at least it better be) but it won't be updated every day or even every other day. The plan is that this story will be exactly six chapters (seven when I make up my mind on whether or not to do an epilogue) but some of them could get pretty long and I'm a perfectionist so...not quite sporadic updates, but not exactly fast. Just FYI.