I do not own any of these characters besides Riley. Sadly.

Chapter 1

Dean watched from a distance, as Jo's smile lit up the group of friends that she was waitressing in the small town bar. Ellen had called Dean and Sam, knowing that things this year would be limited but she made a simple request. It was if they were to pass through Duluth, Minnesota anytime that they were to pick up Jo and bring her with them, until they got back to Ellen.

Sam was back at the motel waiting, or possibly sleeping. Dean didn't really know. He did know that Sam had been beating himself up over what he was going to say to Jo once he saw her again. Dean walked up to the bar trying to get Jo to notice his presence.

"Dean, what are you doing here?" Jo asked sounding a bit irritated. Jo looked at the man that she feared, he could break her so simply, their last encounter was enough to put a down in Jo's following days causing her to seem almost hopeless. She hated that.

"A favor for your mother. She wants us to bring you back to see her, when we pass through that is." Dean said thinking about the last part, Jo gave him an incredulous look. Did he really just expect her to just agree and jump in the Impala willingly.

"Yeah, right." Jo said turning and going to serve a customer with Dean right on her heels.

"Jo, I'm serious here,"

"Yeah and so am I. You should know by now that I'm not just going to jump at the offer to go on a road trip with you and Sam, So I can go see my mother for whatever reason," Jo said snapping causing the table next to her to look at the two. She walked back over to the bar to get something with Dean still with her.

"And you should know by now, that I wouldn't come here if it was an offer," Dean said a little demanding.

"Dean you don't have control over me, I am not going to go with you and Sam to be treated like a little girl, that you think is just another burden." Jo said crossing her arms, what Sam had said when he was possessed had gotten to Jo's head making her think that Dean truly did just think of her as a little sister or school girl. Dean had a confused look on his face now.

"Jo where is this coming from? Look, if you want to help us along the way. I won't say no, just as long as you agree to come see your mom." Dean watched his words around the strangers, but knew that Jo would realize what he was talking about. If she wanted to hunt with them, she could.

"Dean I can hunt on my own. It doesn't really matter that much." She says as she wipes down the bar. Dean could tell this wasn't going anywhere, he didn't know what else to do. He felt obligated to do this for Ellen.

"Jo, please." His husky voice low but loud enough for her to hear. Jo then looked up at him surprised, the look on his face was unexplainable. Just like Dean. He looked tired, and Jo knew he was out of options to offer her. There was something about his look that made Jo feel bad.

"Fine," She said letting out a sigh.

"Thank you," He said and then turning around. "You coming?" He asked.

"Now? I haven't even finished my shift,"

"Its not like you are going to get your paycheck."

"Dean, can I just meet you and Sam tommorow?" Jo asked knowing that Dean wouldn't say no, he was lucky to even get her to go with them.

"Yeah, you know what motel we're staying in?" He asked her.

"The only one in town, whats your room number?" Jo asked before he went out the door.

"14, Night Jo," He said. She nodded and he left. Jo watched as he left, and then let her eyes linger on where he just was. This felt all too familiar. Jo couldn't help but feel, like he was always turning away and the timing was always wrong. Right now she knew better.

Jo waited until the end of the night to break the news to her boss that she would be leaving. When Jo walked over to the older man with the graying beard and gray eyes she looked up at him seriously, without a smile that he knew was always there. Jo always tried to be happy for these people, whether she was or not. She didn't need people wondering what was wrong with her.

"Ricky, I have to go home. Theres a emergency with my mother and I don't know when I will be back," This wasn't a total lie, just a little exaggerated. The look on her face and the honesty in her voice was enough for Ricky to believe her.

"Well I'm gonna miss you, Jo." He says seriously, as Jo looks around.

"I'm gonna miss this, and you," She said before giving the elderly man a hug, she had grown close to him over the last few months, he was like the father figure, Jo missed most of her life.

"Tell me your address you will be at, so I can send you your paycheck," Jo nodded and grabbed a pen from behind the bar and jotted it down on a napkin. She handed it to him and gave him one more hug.

"Good luck"

"Thank you." Jo said and then turned going out of the car and over to her rust bucket of a car. It was enough to get Jo around and that was all that mattered, she drove a couple miles before coming to her apartment building.

Jo shared the apartment with a roommate, her name was Elisha and the exact opposite of Jo, but they somehow ended up becoming friends. Jo counted enough money out for this months lease and then put it in a envelope and wrote a letter saying she didn't know when she would be back, but she would send her share of the apartment for each month if she wasn't there. Jo signed the letter,and left it with the envelope of money on the table. She made her way into her room, grabbing things and stuffing them her duffel bag, filling it with important things and clothing. Lastly she grabbed her fathers old leather jacket, and laid it on top of the bag. She turned and looked around her apartment before walking out and down the stairs that lead out of the apartment. She didn't need her car, the motel was 5 minutes away. She walked letting the warm breeze blow her hair back, she knew talking to Sam was going to be awkward. Jo took a deep breath when the Impala came into her view, she walked over past the Impala and found room 14 that wasn't far away from the car.
Jo noticed the light on inside and she softly knocked on the door, to have it opened by Sam. Jo walked into the room and saw Dean passed out on his bed. Jo walked into the room setting her bag down and looking at Sam.

"Jo look, I don't want things to be awkward and I am sorry-"

"Sam don't apologize. I know it wasn't really you and I don't want things to be awkward between us either." She said to him, he nodded and smiled.

"Maybe I can get some sleep now," Sam said with a laugh.

"You were awake because of that?" Jo asked surprised,

"I couldn't stop thinking of what I would say to you,"

"Get some sleep Sam," Jo said to him meaningfully. Sam was in his boxers and t-shirt anyway, he nodded and went to the other bed laying down.

"What about you?" Sam asked looking at her with a little concern. Jo looked down at the floor, she was tired but no way was she sleeping next to Dean.

"We can share," Sam said innocently, as if he could read her mind. Jo nodded and grabbed her going into the bathroom to change. She came back out with a blue cami and plaid pj bottoms. She turned off the lights and slid in next to Sam, she turned on her side facing Dean. The moonlight lit up his face and made him look angelic, and at the same time like a little boy.

"Goodnight Jo," Sam said.

"Good night Sam," Jo said in a whisper and then watched Dean until she drifted off into sleep.