Dean wanted to save money for college. He was already searching for ways to earn money around his small town. He knew he couldn't rely on his deadbeat father or younger brother, Sam. It was all on him to determine his future. Hell he was only eighteen, an adult, perhaps. Just like his father would say, "I don't have the time" or "You know we don't have the money to do this, Dean".

Fuck this. I'm gonna get a goddamn job, he thought as his fingers moved hurriedly on the helpless computer keys. He was stressing out; senior year started tomorrow and he needed to find his job quickly. He didn't care what the job was, just as long as it paid well.

Google was probably tired of him. He had viewed so many websites on jobs, but none of them satisfied his taste. He was on the verge of tears of frustration. He turned to find Sam sitting on their cigarette-burn covered couch watching satellite television. This was the twenty-first century and satellite television was their best friend for entertainment.

"Sam, do you want to do anything today?" the oldest Winchester asked, trying to hold back his anger. He did his best to be Sam's father and brother since they never knew where their father was, especially on Tuesdays.

"No," Sam replied, the deepening of his voice slightly shocking his brother.

"Come on, Sammy. It's the last day of summer. You don't want to do anything?"

Sam's eyes were glued to the reruns of Tom and Jerry that were playing all day. "No. I don't want to do anything."

Dean sighed disappointedly. He knew he was failing at this new co-parent job. He shut his worn out computer and continued to gaze at his brother who refused to look at him for some reason. "Well, I'm gonna go out and get us some lunch. Anything sound good?"

"No."

Dean stood up from the table and the constant no's were really starting to annoy him. He walked over to his almost brain dead brother and plopped on the couch. His eyes refused to leave his younger brother.

"Sammy, what is it? Why are you acting like this?"

He could see the tears forming in the youngest Winchester's eyes. What the hell? Dean thought.

Sam didn't answer his brother at first. The lack of response and falling tears made Dean's heart break. He didn't know what was happening inside of his brother's mind, but he wanted to get rid of it.

Dean wrapped his arm around Sam's shoulder for comfort. That's when Sam broke. He sobbed as his head made contact with Dean's shoulder. "Sammy? Please tell me."

"Why do we live like this, Dean?"

The oldest Winchester knew exactly what the youngest meant. He was ashamed that he was stuck raising him instead of their father. There was something about this not even a minute long conversation that was stabbing Dean right through his heart. He knew damn well what Sam meant and that their father wasn't the one comforting them.

"I don't know, Sammy. I just don't know," is all Dean could say. He didn't know how to answer without using the most vulgar words around Sam to describe how he feels about his absent father.

"Will Dad ever be back? Do we even have a dad?"

Dean wanted to cry as well; not just because of the frustration of trying to find a job, but because of the rage John built into him. He wanted to believe that his father would be back, but it was impossible.

"Sammy, whatever Dad is doing, I'm sure he'll think to come back to us. But for right now, I'm here for you. All we need is faith, Sammy. Just… pray that Dad will come back to us and treat us like we're his kids, okay? If he doesn't, just know that you'll have me. It'll always be me and you." He rested his head on top of Sam's hair. Please, God. All I'm asking for is for Dad to come back, but not be a stupid, pigheaded man like he always is.

"Okay, Dean. Thank you," Sam said with every fiber of innocence in him. "Will you be there for me at school?"

Dean chuckled lightly. He could hear the slight anxiety in his voice of knowing that he was going to be a freshman. He knew his brother was always one of the outcasts, but that didn't upset him at all because he was going to kick any bully in the ass.

He lifted his brother's chin to where their eyes lined up. "Sammy, you know I will be there for you. Just give me a call if you get lost and I'll do my best to tell you where to go, okay?"

Sam's face lit up with relief. "Okay!" That's the Sam I know, Dean thought as his brother's deep voice exclaimed with happiness.

Dean gave his brother a pat on his shoulder and stood up to retrieve his car keys from the busted table. "Now that you're in a slightly better mood, do you want to do anything on your last day of summer?" Oh God, I sound like the world's cheesiest dad now.

Even though it was about seventy-five degrees out, Dean grabbed his leather jacket that he for some reason still wears despite the hate towards his father. He replaced the emptiness in his pocket with the keys to his Impala and grabbed the trailer home key out of the other.

"Well, I want to help you find a job, Dean. I know you've been wanting to earn some money for us. Don't think I haven't seen your search history," Sam objectively said.

Dean sighed. I should've known I had a tech geek for a brother. "Yes. I am looking for a job because if Dad isn't going to be around to help us financially, then I've got to do something. I can't just sit in this shithole of a home and watch us live like rats, Sammy. I want us to have a better life and I personally need money for college, so yes, I'm looking for a job. But… how could you help me?"

Sam removed himself from the couch and slowly walked towards his taller brother. "I found a job for you."

Dean's eyes widened. "What? How?"

Sam snatched his tiny phone from his jeans pocket and Dean watched him swipe the screen in all directions. Eventually, the younger Winchester grew a smile on his face and practically shoved his phone screen in his brother's face in excitement.

Babysitting job opening! Age of children: 8. Salary: See employer for details. Lawrence, Kansas. Call Kelly Kline at 785-654-3210 if interested.

Dean frowned almost in disgust. "Babysitting? Come on, Sammy. You know that won't happen."

"Dean, you've got to give it a try! Please. I saw you struggling about five minutes ago and this is one that I found last night. I know kids aren't your thing, but please give it a try. I'm begging you. Maybe Mrs. Kline would give you a good amount of money," Sam pleaded.

Dean glanced at the offer on the screen in front of him. He squeezed his eyes shut; he didn't think he would be good at this job. He despised children. Well, besides Sam. "You know I don't work well with children."

Sam rolled his eyes and shoved his phone back in his pocket. "Dean. You've taken care of me ever since I was a baby and you were only four. Don't give me that crap. You never know, this actually could be good for you."

Why is Sam so good at arguments?

Dean released another deep, nervous sigh. He also hated phone calls. "Show me the phone number. I will give Mrs. Kline a call and see if this job is the one."

Sam's body squirmed with excitement and pulled up the online advertisement again. "Just read me the number," Dean requested as he took out his flip phone.

"Uh… 785…" Sam copied from his screen.

"Yeah."

"654."

"Uh-huh."

"3210."

Dean typed the announced numbers into his cell and nervously dialed it. He could feel his heart thumping and his stomach doing somersaults. His frown was glued to his face. He waved his hand at Sam to signal that he wanted some privacy. Sam groaned with frustration and stormed out to the Impala.

Right when the door slammed, Mrs. Kelly Kline decided to answer. "Hello? Kelly Kline speaking."

Dean cleared his throat. "Uh, hello!" he practically yells into the phone. He immediately regrets his decision. He hesitantly brought the phone from his ear to the front of his face and his thumb hovered over the end call button. He knew it was over after one word.

"Hello, sir? May I help you?" he heard Kelly's sweet voice ask. She sounded so soft to where it was almost a whisper through the little phone.

Dean felt his heart jump at the sound of her voice. He returned the phone to his ear and smiled lopsidedly. "Hello, ma'am. My name is Dean Winchester. I saw your ad online about a babysitting job. I am very interested in applying for this position, ma'am."

"Oh, how wonderful! I'm delighted to know that someone finally took notice of my offer. Please come by my house later today, Mr. Winchester so I can meet you and hopefully give you the job. So far, you sound like a fantastic young man."

Dean chuckled. He hadn't been called that at all in his life. "Of course, Mrs. Kline. May I have your address, please? I will be on my way right now, ma'am."

"1961 North Running Ridge Road. I will see you soon, Mr. Winchester." Her voice reminded him of his mother's. He could already feel the need to want to help this woman. Just because she was making him believe she was Mary's duplicate.

"Of course, ma'am. I will be on my way right now. See you soon." He flipped the top of his phone over the bottom. His smile never left his face. He glanced down at his clothes. Leather jacket. Black t-shirt. Ripped jeans. Boots. His classic look.

But this just won't impress Mrs. Kline. I need to find my best clothes.

He rushed to his bathroom-sized room and scrambled through his dresser. He wanted to replace his dirty jacket with his red and black flannel, his absolute favorite. He needed to replace his ripped jeans with his clean, non-hole jeans. Which is exactly what he did. He kept his books because his sneakers couldn't top them. By the time he finally changed his clothes, his hair spiked up as if he were electrocuted. He gasped at the sudden horrific sight and rushed to the sink in the bathroom. Wetting his hands, he ran them through and flattened his hair. He borrowed Sam's comb and attempted to side his hair.

He smirked when he was finally satisfied with his better look, he sprinted out the trailer home and jumped into the Impala. Sam sat in the passenger seat anxiously. "Well? Did you actually talk to Mrs. Kline?"

The Impala's engine screamed and the radio blared Led Zeppelin. Sam covered his ears when Dean zoomed in reverse out of their short driveway. "Dean!"

"We're going to Mrs. Kline's house, Sammy! I'm gonna get a job and we're getting a better life! Just me and you!" Dean hollered over the loud rock music. He was way too excited to turn down the volume that was bothering Sam. He knew he was speeding down the highway, but at that point, there was no care in the world.

Sam suffered a solid twenty minutes. Listening to loud, screaming rock and roll was one of his pet peeves. He liked the genre, but not at a volume of thirty in a small car. He thanked God when Dean finally lowered the volume to a normal one when they reached the driveway of Kelly Kline's mansion.

"Wow…" Sam managed to say after processing that Kelly was in fact a millionaire.

The oldest Winchester couldn't believe how grand the mansion looked compared to its neighbor. The house was wider and taller than any other house the boys have seen. The beautiful garden in the front perfected the house as well as the small fountain and lengthy gravel driveway. The house was made of tan stone and the red roof was outstanding. Everything about this house displayed utter wealth. How lucky Dean was to be able to drive on this driveway.

"Uh, Sammy? Did you lead me to a millionaire's house?"

"Maybe… but I didn't know."

The boys' eyes remained widened, even when Dean found a spot in front of the large three garages to park Baby. When she shut off, the boys slowly departed her. Their eyes were still glued on the house. This fucking castle of a house.

"Are you sure we're at the right place, Dean?"

Right when Dean was about to answer, a small, average-aged woman opened the door and practically skipped to them with glee. She had dark, straight hair down to her shoulders and looked no older than forty. Her eyes were a mixture of blue and green, but the green stood out more. Her mouth was small, but her smile seemed big. When she approached the two boys, she hardly passed Sam in height.

"You must be Mr. Winchester! Very nice to meet you, young man!" she exclaimed as her hand claimed Dean's and shook politely.

"Mrs. Kline, I assume?" Dean asked nervously.

She nodded softly and gasped, "Gosh, you are much more handsome than I thought you would've been."

Dean felt a blush form on his cheeks and he said, "Thank you, ma'am. If you don't mind, I have my younger brother, Sam, here with me."

Sam did his best to look as professional as possible, but he knew he still looked like an amateur. The kind woman didn't seem to mind. "Hello, Sam."

"Nice to meet you, Mrs. Kline."

"Oh, Dean, you already seem like the perfect babysitter. I just can't wait for you to meet my son. But first, I have to give you a tour of my house."

"Mrs. Kline, if I may say, you have the most beautiful house I have ever seen," Dean complimented. Of course he was impressed with the house, but he knew compliments in interviews were the way to go.

"Oh, deary, thank you so much," Kelly almost whispered as she put her little hand on Dean's large shoulder. "Please, enter my home." She stepped aside from them allowing them to step on the beautiful small stairs that raised her porch.

By the time Dean had opened the castle-like door, he was in even more awe with the mansion. Glass and porcelain was all that flashed in his eyes. Everything looked so expensive that it made Dean feel even more broke.

Sam followed Dean and mirrored his starstruck expression. "My son, Jack, is who the ad was for. He is eight years old," Kelly said as she gently closed the delicate door. "He's out with his friend right now."

"Does his school start tomorrow, too?" Sam asked.

"Yes. He will be in second grade at the elementary school just down the road. I hope this drive wasn't long for you boys at all."

Dean faced the older woman. "No ma'am. The drive here was amazing."

"I'm glad. Please, let me show you around my home." She led the way around the house, praying internally that the boys would be able to find their ways around it.

As she led them into the massive kitchen, Dean slightly mumbled, "Son of a bitch…" It was quiet enough to where Kelly could not hear him, but Sam nudged him on the arm.

"This is the kitchen. This is where Jack usually does his school work if he has any. Once you get settled in, you are absolutely welcome to anything."

Once I get settled in? Dean stupidly thought. Kelly signaled for them to follow her once again into the living room that was bigger than their trailer home.

The room was made up of two large couches, too many comfortable couches, a glass table that was as long as the kitchen table, and coffee tables that seemed breakable by a simple touch. The TV only made the room look more golden as it stretched a solid seventy inches. Flower-filled vases rested on the ice tables and Dean felt himself walking slowly by them.

"This is the living room. Please be careful around the coffee tables. I had saved so much money for those and the last thing I want is for them to be broken," Kelly softly requested.

Dean gave her a small nod and smirk. "I will be very careful, ma'am," he spitted back her words. He knew he sounded like a peasant when he said that, even though this whole house made him feel like one.

"Usually the remotes are on the ledge in front of the TV. If they aren't, then they're shoved in the couch cushions because Jack finds that funny sometimes, but it really gets on my nerves," Kelly said with a chuckle. "Please follow me, boys."

She continued to walk around her house and the boys followed her like dogs. They had expected her to lead them up the stairs, but she refused to let their feet touch the glass stairs. Of course the stairs were glass. Everything in this house had to put the Winchester's finances to shame.

"Up the stairs and to the right are two bathrooms and Jack's bedroom. To the left is the guest bedroom that has a bed and a pullout. Castiel's bedroom is also to the left."

"I'm sorry, who's Castiel?" Dean asked with confusion.

"He's Jack's older half brother. He just recently got a job here and he's going to live here."

"How old is he?" Sam asked.

"He'll be 25 in a few weeks. He's Jack's father's son. Their father died in a car crash when Jack was a baby."

"Oh, I'm so sorry, Mrs. Kline," Dean replied with sympathy.

She let out a soft laugh. "Don't worry about it, darlings. Castiel and Jack have both adjusted to the change. I know the tour was short, but I really try to avoid going upstairs with shoes on."

The boys smiled at the woman and Sam said, "Your house is beautiful, Mrs. Kline. If Dean gets the job, I can assure you he is the cleanest person around." He gave Dean a smirk and the oldest Winchester rolled his eyes.

"I believe that, Sam. You dressed very nicely, Dean. Very appropriate for this interview, if you want to call it that," she laughed. Dean and Sam both returned her laugh nervously.

"Thank you for having us here, Mrs. Kline. I'm very interested in this job, and I hope I am able to meet Jack," Dean said with all the hope in him.

Kelly sighed and took a glance at both him and Sam. The look she had on her face expressed satisfaction. Her green eyes shone when the sun reflected on them through the windows. She was clearly the nicest woman the boys have met. Why couldn't we have a life like her's? Dean thought.

"You know, how would you feel if I told you that you got the job?"

Dean and Sam's eyes widened. "Wh-What?" Dean asked with a mixture of joy and surprise.

She chuckled lightly. "You boys are clearly the right fit for this job. I've interviewed a few other people, but you boys have been the absolute best. You dressed very appropriately and you two just scream 'babysitters' to me."

That last comment made Sam laugh at Dean because he knew that was not true whatsoever. "Well, thank you so much, Mrs. Kline. I cannot thank you enough," Dean replied. "When would you like me to start?"

"So here's the deal. My mother lives in France and she's been very sick lately. The doctors over in Paris have actually requested me to come stay with her until she's better. Honestly, I think I will be over there for a year or so. That's why I am overjoyed to finally have someone stay here with Jack. I know Castiel will be here, but he's always busy. I leave tomorrow night for Paris. I will also get you both settled in tomorrow. You two can have the guest bedroom."

That's when Dean's heart dropped. Live in this castle of a house? Is she really asking that? "Excuse me, ma'am?"

"Would you boys like to stay here? Live in my house?" she asked, praying to God that they would agree.

Sam's insides were doing front-flips and Dean couldn't even explain how he was feeling. The widest smile was forming on his face. "If you don't mind, I'm going to have a word with Sam, Mrs. Kline."

"Of course, dear."

Dean gently pulled Sam away from Kelly. "What the actual hell did you lead me to?" he mumbled.

"The best offer of your life," Sam whispered back. "Dude, she's letting you live in her mansion for a whole year. You can't pass that up. I admit, I may have already spoken to her about you and look, she likes you a lot. Don't give up the chance to help her and ourselves out."

"What did you say to her?"

"Dean, you obviously know I didn't say anything bad. She's literally giving you the job. Please take it."

Dean wanted to cry tears of joy. He couldn't believe that almost an hour ago he was stressing about finding a job and now he's finally employed. All thanks to his brother that was having a meltdown that same hour ago. He's right. I've tried so hard and this could be my only chance.

He slowly walked over to Kelly with the happiest smile. "I will take your offer, Mrs. Kline. I can't even explain to you how thankful I am for this opportunity."

"Oh trust me, Dean. I can't tell you how happy I am to find you," Kelly replied. "Also, by the time I come back, I will get you your money for college."

Dean's eyes probably didn't know how to close after today. His eyes remained wide. "You know about our-."

"Yes, darling. Sam told me all about your financial problems… and about your father," she said with every fiber of sympathy in her. Dean squeezed his eyes, trying not to show his anger about John. "Since you're helping me, I most definitely want to help you. Before you go to college, I will reward you with $100,000."

"Oh my God!" Dean slightly shouted in surprise. He couldn't believe that he was going to get $100,000 just for becoming Dad again for a whole year. "Oh… sorry. I'm just in shock that you're willing to give me that much money. Really, you don't need to."

"Please, Dean. Let me give you what I don't need," Kelly said resting her tiny hand on his arm. "Now if you don't mind, since I know tomorrow is the first day of school, you can come by here when you're done and settle in. Jack takes the bus to and from school, so pickup and dropoff for him won't be a problem for him. I'll just go over the last things tomorrow."

"That sounds great, ma'am. I can't wait to meet Jack," Dean said with excitement that was hard to control at this point.

She chuckled, "I'm glad. Just wait until you meet Castiel. You'll really like him."

What Dean didn't know was about how accurate she was about Dean liking Castiel. The oldest Winchester didn't know what was coming the next day, but he is in for a hell of a ride.