Holly walked into the dinner and grabbed her apron. It was going to be another long day for her. As she began to start the coffee, she heard someone sit down at the counter, "So are you going to spill that on me today?" Holly turned around and saw the guys from yesterday, "Because I got to tell you, it hurt like hell."

"I will do my best to keep it in the cup today." She said giving him a soft smile.

"That's too bad because I kind of liked you touching me." Dean said and realized it came out wrong when she glared at him, "You know, in a non pervert way."

"No I think you meant it how it sounded."

Holly turned away from him and grabbed a coffee cup and sat it in front of him, "So when do you get off?"

"Why would I tell you that….Dean?"

"You remembered my name. That's a good thing. I must have done something right."

"I just have a good memory but I am guessing you don't remember mine."

"Are you doubting me…Holly."

"So you do remember. I have to say I am impressed."

"Impressed enough to go out with me?" he asked and Holly looked at him.

"I don't think so." She said and walked around the counter to start refilling the salt shakers.

Dean got up from his chair and followed her, "Why not?"

"Because I know your type." She said and moved to the next table, "Besides did you go out with Amber last night?"

"No I didn't. Thank to you I had to go out and by new pants."

"Sorry about that."

"What do you mean you know my type?"

"Love em and leave em right?

Dean scuffed, "No"

Holly grabbed the last of the salt shakers and walked back over to the counter, "So you see you owe me for the coffee so you have to go out with me." Dean insisted.

"Ok I will give you your breakfast for free then."

"No thank I already ate."

"Then why are you in a dinner at 6 am." Holly asked.

"Because I knew you would be here."

"How did you know that?"

"I called and asked when you would be working again."

"Are you stalking me Dean?"

Dean looked at her and truth was he kind of thought he might be, "No I just happen to find you interesting."

"Interesting?"

"Look I don't know the right answer to this so just go out with me." He asked again.

"Answer is still no."

Dean nodded and got up, "Alright but don't think I give up so easily Holly." He said and walked out the door. She bit her lip slightly and shook her head. She knew he would be back.

Over the next five days, Dean came back everyday to ask her out and every day she said no. Part of her wanted to say yes but for some reason she didn't trust herself with him. She knew all it would take was for her to say yes once and she would be hooked.

Holly turned off the lights and locked up the doors to the dinner. It was almost eleven and the wind was cold on her as she started across the parking lot, "Hey pretty lady." She heard someone say and turned to see a tall man walking over to her.

"Hi" she said and turned around and proceeded walking to her car.

"Where are you off to on this fine evening?" he asked her and we walked closely behind.

"I really don't see how that is any of your business sir." She said and when she looked at him once more she could see he was clearly drunk, "Should I call you a cab or something? She asked. She always had a big heart and wanted to help others.

"I just thought I could go home with you." He said and grabbed her from behind, playing with her hair, "You smell so good. I could just eat you but then again maybe you want me to."

Holly closed her eyes and tried to grab her keys but the man grabbed her arm, "Why be in such a hurry? I just want to have some fun with you and I promise you will like it."

"Please….please just let me go and I swear I won't say anything about this."

"I know you wont but if I let you go then what fun would that be? I just want to her you beg for me. I have been watching for a long time now and I have just been waiting for the right moment to have you all to myself."

A tear rolled down Holly's cheek as he pushed her over to the car. She knew what was about to happen to her and it scared her more than anything. She knew if she yelled it would only make him made and the chances of anyone hearing her were slim, "Please don't do this." She begged.

"I am just going to take care of you and trust me you will love it. No open the door." He said and he pushed her up against the car.

"Hey! Something tells me she don't want to go with you buddy." Holly looked up and saw Dean walking over to the car 'thank god' she thought.

"And who the hell are you?"

"Someone who is about to kick your ass if you don't let her go and I don't like to ask twice."

The man let go of Holly and pushed her onto the ground, "I don't see how this is any of your business."

"Well I am making it my business. Obviously you have had far too much to drink and I think you need to leave before something bad happens."

The man walked closer to Dean and got up in his face, "What are you going to do if I don't leave?"

Dean smiled at him before he used his right fist to punch the guy in the stomach as his rleft fist connected with the man's jaw. The man instantly fell to the ground and Dean looked over at Holly, "I told you I was a nice guy."

Holly just looked at him, still terrifies as he went over to her, "My hero" she said and looked over at the man, "I would hate to see you when you get upset." She said and Dean started to help her up, "Ouch."

"What's wrong?"

"I scratched me knee when I fell."

"Come on I will drive you home."

"What about him?"

"He'll be fine….maybe." Dean said and walked Holly over to him car. She climbed inside the driver's side and slid over.

When Dean got inside, he closed the door and Holly looked over at him, "Thank you." She said softly.

"You don't have to thank me. I am just glad I was there."

"Why where you there anyways?"

"I was coming back to ask you out for the seventh time." He laughed, "Lucky number seven."

"After what you did tonight I think I have to say yes."

"No you don't." he said and started the car.

"What if I want to say yes?" asked Holly.

"Then I would love to take you out. Man, stop begging." He said and Holly opened her mouth and scuffed.

"You are just a little cocky aren't you Dean…I don't even know your name."

"Winchester."

"Well hi Dean Winchester. I am Holly Spencer."

She reached out her hand and he shook it. Holly looked done at their hands and noticed something. They fit perfectly together.

Holly rolled over in the bed and looked at the clock, it was two a.m and she still couldn't sleep. Maybe it was normal to think about your first love before you remarried. There was nothing wrong with her. It was just cold feet. She closed her eyes and tried her best to drift off to sleep.

One week later

Holly got off work and as always, Dean was waiting outside for her but he wasn't looking as happy as he normal did, "Hey you." He said and Holly walked up to him and kissed him on the lip.

"Are you ok Dean?"

"Yeah it's just that…well you remember the other day when I told you what my family did?

"Yeah the hunting thing which I still find a little strange."

"Well my dad called and well I have to meet up with him in the morning."

Holly's face dropped, "You're leaving?"

"I don't want to be I have to go but I will be back as soon as I can."

"You promise."

"I promise. Someone has to keep you safe." He said and cupped her face. He kissed her passionately on the lips, trying to savor the taste. This was the first time he would ever have to leave someone and truly miss them and it was strange because he had only known her two weeks.

"Do you want to go back to my place for a little while? My aunt is out of town so we could watch a movie or something."

"Sounds like a plan." He said and she got into the car and they drove to her house.

Later on that night, they were sitting on the couch and Holly was curled up next to Dean with his arm draped over her shoulder, "Hey Dean?"

"Yeah?"

"I am going to miss you." She said looking up at him, "I kind of like having you around."

"I am going to miss you too. You arent so bad yourself."

Holly looked back at the TV and bit her lip. What he did for a job scared her and she wasn't really sure if she would ever see him again so she had to make the most of his last night here.

She stood up and looked at Dean and smiled. Holly grabbed his hand and pulled him off the couch, "What are you doing?" he asked her.

"Just follow me." She said and let him into her bedroom and shut the door.

Dean turned and looked at her, "Not that I wouldn't love to do what I think we are about to do but….are you sure because we don't have to do this."

"I'm sure. After all who knows when we might see each other again?"

Holly walked over to him slowly. Her hands were shaking as she pushed the over shirt off of his shoulder. Dean reached up and started to unbuttoning her shirt, taking his time. He could tell she was a little nervous.

This was only Holly's third time at this so she was still a little new. After her mother got pregnant at fifteen by a man she didn't know and left her under they car of her aunt, she always promised herself that she would be a hundred percent sure when she slept with someone.

Holly stepped back and took her shirt off followed by her jeans as Dean did they same.

The only thing left on them was their underwear. Dean walked over to her and lifted her up and carried her over to the bed. He laid her down gently and lay on top of her. He pushed a strand of hair from her face and kissed her once more before making love to her.

Holly signed as she tossed and turned, trying to get those memories out of her head but she could. The though of her and Dean's first time made her smile. She remembered how gentle he was with her and that was the night she fell in love with him. Holly never though she would fall in love so easily but there was just something about Dean. Who knew that night would forever change her life?

One Month Later

Holly sat on her bed as her phone rang for the tenth time. It was once again Dean. She couldn't talk to him, not after what she found out the day before. He would hate her and never want to see her again and she couldn't handle that. The best thing for her to do was move on without him. That way she wouldn't get hurt.

"Holly you have company!" May yelled down the hallway.

Holly just sat there. She didn't want to see anyone. How could she have been so reckless? She heard a knock at the door and looked up, "Who is it?" she asked.

"It's Dean."

She closed her eyes causing the tear to roll down her cheek, "Go…go away Dean."

"Not until you talk to me and at least tell me what I did."

"You didn't do anything. Just please leave me alone."

"Damn it Holly just open the door." Holly wanted to open it but she couldn't. His life was busy enough right now, "Fine. Have a nice life." He said and she heard him walk away. It was long before she heard the front door slam and the car drive off.

"Holly can we talk sweetie?" May asked through the door and Holly got up and opened it, "You can't stay in here forever. You need to eat something and what did you say to that poor boy."

"May not now. I told you I just don't feel very good right." She said and walked over to her bed, picking up her teddy bear and holding it tight.

"You know you aren't fooling anyone." May said and took a seat next to her.

"I don't know what you are talking about."

"I think you do. I know the look."

Holly's tear became stronger and May just wiped them away, "What are you so afraid of Holly? You know you love him."

"I don't really know him Aunt May so why would you say I love him?"

"Because I know you Holly. You have a big heart and I always knew when the right boy came along all it would take was one kiss."

"It's not that simple. What if….what if he doesn't feel the same way."

"You have two choices here. Either listen to what your heart is telling you and talk to that boy or spend the rest of your life thinking about what could have been."

"I'm scared." Holly said and May pulled her niece into a hug.

"Everything will be ok. I know this so trust me. Call him and why you are at it you may want to mention the other thing."

Holly looked up at May and wiped her eyes, "What other thing?"

"Like I said, I know the look and falling in love is not what is scaring you right now." She said and got up off the bed, "Good night Holly."

Holly just fell back onto the bed and looked up at the ceiling. It wasn't long before she heard a knock at her window. She got up and walked over and saw Dean standing there. She opened the window, "Dean what are you doing here?"

"When have you ever known me to give up easy?" He said and climbed into her room, "Now I am not going anywhere until you tell me what's going on? We were fine two days ago."

Holly turned away from him, "I have just had something's going on the past day."

Dean walked up behind her and wrapped his arms around her, "Can you at least tell when why you have been avoiding me? Did I do or say something?"

"No"

"Then what is it?"

Holly took a deep breath and turned to him, "I need to tell you something and I don't know how."

"Ok so tell me. How bad can it be?"

"I love you." She said and watched his facial expression change.

"Wow I wasn't really expecting you to say that but….."

"You know what just forget it." Holly said and was walking toward her door when Dean stopped her.

"Hey you didn't let me finish. I just wasn't expecting you to say it first because I want to tell you that I loved you first."

There was a sparkle in her eye, "Really?"

"Yes really and I can't believe you were avoiding me because of something like this."

Holly bit her lip and walked away from him, "There's more."

"Ok so your last big secret went well so what are you worried about?"

Holly turned to him and knew she just had to get this out, "I'm pregnant."

Dean turned his head to the side, "Come again?"

"I'm pregnant Dean. I found out yesterday and I wanted to tell you then but I just couldn't."

Dean just sat down on her bed and ran his fingers though his hair, "Ok maybe that is the last thing I expected you to say."

"Dean I am so sorry about this." Holly said and sat down beside him.

Dean turned to her, "why are you apologizing? It wasn't your fault." Holly began to sob and Dean pulled her into his chest, "Please don't cry baby. Everything will be ok. I'm not going anywhere."

"What are we going to do? I can't be a mother."

"Look at me." Dean said and she looked up and him and he wiped away her tears, "You are going to be a great mother."

"You really think so?"

"I know so." He said and kissed her.

Holly was now holding her wedding band in one hand and her engagement ring in the other. Dean would always have her past but Jack had her present but the question was, who had her future?

A/N: Ok not a lot going on in the chapter but no you know how Dean and Holly got together. Hope you liked it and this had to be my longest yet. So three chapters in two days. Show me some love people. You keep reviewing and I keep posting. Thanks again for reading and adding as your favorites. You guys are great : )