Disclaimer: I do not own Supernatural or it's characters. Nor do I own the song 'This is My Idea' from Swan Princess - from which this story is based. A small part of this chapter is also inspired by the Bon Jovi song "I'll Be There For You."

Author's Note: I know, I'm a bit cracked out sometimes. But if Bobby Singer had a daughter, I think this is a plausible scenario.

II.

Til now I never knew
It was you I've been dreaming of.

Ashton Singer examined her own face for the first time since she didn't know when. She sighed and wiped at a stray smudge of eyeliner. She was wearing a short blue and white striped dress with white flats. Yes, indeed, the reluctant daughter of Bobby Singer was dressed up for a date with Dean Winchester. The door was firmly locked in case she decided she didn't want to go through with it - but she found herself rising from the short stool in front of her vanity and opening the door. Bobby was waiting outside of her door and smiled. He was pleasantly surprised that she had put as much effort into getting ready for this date as she had for any of her prior dates.

She felt like she was going to prom as her father hugged her. Bobby and Ashton were not exactly known for being super affectionate as father and daughter, so Sam was compelled to watch in amazement as Bobby looked at his daughter in pride. He was busy reading another book of Ashton's - this time the Count of Monte Cristo - before she exited. Dean was outside, already in the car - too nervous to stay inside and wait for her to be ready.

She was carrying a small white purse as she forced herself out of the door way and looked into the car. Dean stared back as she shrugged. He couldn't help but laugh. She looked as nervous as he felt and when she got in the car beside him the anxiety at last eased. She was dressed up, and Dean thought that girls who didn't like their dates didn't bother with dressing up. Dean pulled the car into drive and left the Singer Salvage Yard cautiously.

Bobby and John, who had made it out to South Dakota for the occasion, were not far behind. The eldest of the Winchester and Singer clans made their way to the restaurant where their children were eating and were not surprised to see that they picked a window seat. Dean had an arm around Ashton who was chatting with kids from her graduating class. They were laughing and looked like they were just two normal teenagers on a date. John even saw Dean kiss Ashton's temple once - a gesture he had never before witnessed from his son. They stayed there until around 10, and got to the movie theater about ten minutes later.

"Our fathers are following us like creeps," Ashton noted, her arm wrapped comfortably around Dean's waist. Her head was resting right below his neck.

"You knew they would."

"But they're like, five feet behind us in sunglasses and reading newspapers," Ashton replied, "They're not even trying to be inconspicuous!"

John chuckled from behind his newspaper.

Dean leaned in close, "I have an idea of how to ditch them." He whispered this so as to not alert their fathers of any mischief. When he glanced back at their fathers, neither seemed to be aware of what he had said.

"Really?" She smiled.

Dean nodded, "Just follow my lead."

Dean Winchester could certainly be sneaky when he wanted to be. First, he chose seats in the very back of the theater so that Bobby and John would have to turn around to watch them, lest they sit right next to their kids and end up screwing everything up. Second, Dean had chosen a horror picture to see. The dark scenes were perfect for a quick, conspicuous getaway. Indeed, within the first half hour of the film the two had fled the theater and escaped to the safety of Ashton's car. They took one look at each other after driving off and parking in a secluded area, and started making out.

When they got home, John and Bobby were sitting on the couch nonchalantly. John was describing to Bobby the last hunt he had been on (a shape-shifter, again). They both looked up at their children expectantly, and both children simply smiled back at them. "I'm going to bed," Ashton said and escaped into her room quickly before they could interrogate her.

The next morning she woke up to Sam's face staring at her. She blinked and pushed his head away as she rolled over. She tried to fall back asleep, but Sammy persisted in annoying her. "Please, please tell me that you didn't have sex with my brother." Her eyes popped open and she turned around so fast Sam was sure she had given herself a slight case of whiplash.

"Of course I didn't!" She screeched.

Sam smiled slightly, "Good."

It was another hour before she was out of the shower and ready for the day. To Sam, it was nice to see her in regular clothes again. Her dark hair was messy and curly. She smiled as she headed out back in a pair of black shorts and an old Bon Jovi t-shirt that Dean secretly wanted to steal from her. It wasn't exactly a mystery where she was going - Bobby had told both he and Dean that Ashton was still working on the Mustang. She was surprised, though, when she found Dean shirtless, sweaty, and covered in oil. He closed the hood as she approached and was wiping his hands on a dirty rag. He turned around and was sitting on the hood of the car when she approached.

"Does it run now?"

Dean jumped, slightly surprised by the added presence, but nodded none the less. She smiled, pleasantly surprised, and found herself running into Dean's arms. He hugged her tightly.

"Why did you fix it?" She questioned. Admittedly, Ash had been struggling to find out what was keeping it from running properly. She had too much pride to ask her father, Dean, or John for help - but was now visibly glad that Dean had helped her out.

He shrugged, "I knew you needed help."

Truth was, Dean had just wanted to impress her so that maybe he could try the dating thing again. After all, he had made an ass out of himself towards the end of the first date and could surely make up for it. He more than made it up on the second, third, and fourth dates. Sam started joking about the wedding date - he had never seen his older brother go on more than two or three dates with a girl unless she was having sex with her, and having sex Dean and Ashton weren't.

"Where are you two going now?" Bobby asked from the kitchen as he saw Dean pulling his daughter out of the house once more.

"He won't tell me!" She exclaimed and the screen door slammed behind them. Bobby looked over at Sam from his seat at the kitchen table and raised his brows.

Sam laughed as Bobby put a plate of food in front of him, "Dean's trying to be 'romantic'."

...

"Dean, where are you taking me, anyway?" Ash asked as they drove out to the middle of nowhere. She was surprised Dean could keep a secret from her for so long. It had been almost a week! It took at least forty-five minutes to get to where the oldest Winchester brother wanted to go. Ash was surprised; he hadn't taken her anywhere particular. It was literally the middle of nowhere. A dirt road led back to a tall oak tree surrounded by high, surprisingly green grass. He parked the Impala that his father had recently given to him, and looked over at her. There was a smirk on his handsome features.

Ash was no fool; she knew what exactly what he had wanted as soon as he parked the car in such a desolate locale. Whether he would get it or not was not was still a mystery to her. It all really depended on how he acted towards her. She was surprised how sweet Dean could be when he wanted something. Ashton had never seen Dean suck up to anyone to get what he wanted, but had often heard from Sam of his dating feats. She knew he was charismatic and charming, but she never knew that it would work on her.

Dean himself was surprised that he could charm his way into Ashton's pants. He thought she would refuse, but she didn't. It was, at that time, the best day of his life. It didn't last long, however, because Dean knew he was going to have to say goodbye one day. He wasn't nearly prepared for her reaction, nor was he really ready to leave her. And so, both of them would lose their happiness.

It was only a few days later, Dean couldn't remember how many, when he had to be the bad news bear. They were sitting on the hood of one of the many junked cars in Bobby's 'backyard' eating soft-serve Ice-Cream from the place up the street with the turtle-mascot. It was a perfect summer day. The sun was hot, the wind blowing gently. Ash was wearing an outfit that looked like it came from Daisy Duke's wardrobe on Dukes of Hazzard. Dean was surprised that Bobby let Ashton stroll out of the house in it. The shorts she were wearing, Denim cut-offs that were short enough to be considered hot-pants, fit her to a 'T.'

Dean found himself wanting her all over again. He glared momentarily at his younger brother who was also out in the sun enjoying an ice-cream cone. Sammy was cross-legged in the dirt, hardly paying attention to Dean or Ashton. The eldest of John Winchester's brothers inwardly groaned. Was this what it was like to break up with a girl you actually liked? Dean thought it was. It was going to be hard, maybe too hard, but John had told him that he couldn't do this for him. And Dean knew that, but he wished that John or Sam could all the same. Then, maybe Ash would hate them instead of him.

The ice-cream cones and Sammy gone from sight, Dean studied the young woman next to him. She'd come out of the other side of this okay; she was always stronger than Dean had thought. One day, she'd find someone that would be able to stay with her. Dean was convinced he wasn't that guy – even if John and Bobby had planned it that way. John had grown almost obsessed with killing the thing that killed their mother. He always insisted that they were getting close.

"Just a few more miles," John would tell his sons, "A few more months. You'll see."

The miles and the months passed all the same and they were no closer to whatever it was that killed Mary now than they were ten years ago. Dean wrapped an arm around Ashton, who in turn kissed his cheek, "What's wrong with you, Winchester?"

Dean looked up at her accusing green eyes. He couldn't lie to her, and he thought that maybe he loved her. He had known her for as long as he could remember. He didn't want to go. He wanted to stay here with her, but he knew he couldn't.

"Dean?" Her eyes were wide, and Dean wondered if she knew this was coming.

Dean nodded, more to himself than to her, "We're leaving soon."

"I expected you would be," She replied, coolly. It was around this time when they usually left Bobby's piece of South Dakota, yes. But she didn't quite understand.

He shook his head, "You don't understand, Ash."

"You always leave in mid-July. Why would this year be any different?"

Other than the fact that Ashton would probably be off at some Ivy League college or an art school while Dean would be hunting monsters that tried to eat people? Oh, nothing was different.

"We're leaving Ash, as in, we're not coming back. Ever."

It took a minute for her to gather the information enough to comprehend. A look of pure confusion and anger distorted her usually gorgeous features, and when she was angry she sounded southern. Her accent would come to her and she would sound more like Bobby. Dean had expected all of these things, what he didn't expect was the slap in the face that came.

In their summers together he had suffered worse injuries: black eyes, broken bones, a bruised tail bone. But this was the one that felt worst. He knew he deserved it. Sammy and Dean left two days later. Ashton had not even come out of her room to say goodbye to Dean, and she would not allow him in either.

Later that afternoon, Ash left her bedroom and found her father reading lore about chupacabras. Her eyes were blood-shot, her hair stringy as if she not had a shower in a few days. Bobby set the book aside and motioned for his daughter to sit next to him. Instead, she sat on his lap and cried on his shoulder. (Literally on his shoulder, he felt the flannel dampening there.) The best way he knew to comfort his daughter was to rub her back and tell her it would be alright - but he couldn't do it this time.

"They'll be back," Bobby told her.

She shook her head, "It won't be the same. They'll stay for a day or two, then move on. We'll just be a free place to stay and eat. I don't want to see him again, Daddy."

It wasn't often that Ashton called her father "daddy," and she only played the innocent card when she needed to. He understood, and as much as he wanted to hate Dean for breaking his daughter's heart - he couldn't. He'd promised John he'd take care of those boys and he intended on following through with it. Besides that, he knew Dean didn't feel good about it and he understood why he had to do it. Bobby had seen the way John had been lately.

"He didn't want to leave," Bobby told his daughter softly, "Boy may be an idjit, but he wouldn't try to hurt you."

"Only because you or John would shoot him." She replied.

Bobby chuckled softly; he couldn't help it. Then he added, "Ashton, he had to. He didn't want to, but he had to. Do you understand?"

"Does it have to do with Mary?" She asked, quietly.

Bobby nodded.

"We don't go looking for the demon that killed Mom," Ash said, for the first time in her life sounding naive and unknowing.

The older, wiser Singer sighed, "That's because I didn't need to. There are some men like me, who can live their lives without vengeance or regret ever on their minds. It doesn't matter how precious something is if it is ripped away from them, they take it with a grain of salt and let the world go on as it would. Then there are men like John Winchester. He doesn't think Mary can rest as she ought to unless he finds and kills whatever it is that killed her. It's the only thing that's on his mind nowadays. It was easier when they were younger to flirt with the idea of them living a normal life again, and it seems impossible to John now - probably Dean too. You and Sammy, you've got a chance to get a different life. John, Dean, and myself don't have that chance."

She looked up at her father, wide-eyed and tired. Ash stole away to her bedroom once again in a few minutes and Bobby wondered if she would come out of the other side of this for the better.

"Huh," Sammy said to his older brother with a letter in his hands.

Dean looked over at Sam and raised a brow, "What is it?"

Sam shrugged, looking down at the letter once again. He continued reading. So far the letter told him to not expect to see Ashton when he got back into town. She would not be there. In fact, Ashton Elizabeth Singer wasn't even going to be in the same state anymore. This, of course, upset her father but he knew that this was for the best. Ash was going to an art institute in California. Bobby had to move her in next week. She didn't know to choose photography over drawing or vice versa.

"What're you reading now, geek boy?" Dean asked, ruffling his brother's hair as he feigned concentration on the highway in front of him. All he could read was "Sam." The handwriting was Bobby's - Dean could tell that without having to read it.

"A letter," Sam said, which really didn't answer his brother's question. He didn't plan on answering Dean's question, at all. When he asked "what're you reading" he meant, "why did bobby write to you." Sam could tell by the way that Dean was barely paying attention to the road.

"From?"

Sam looked up at his brother, but didn't say anything.