Dean and Sam had got to May's house around four on Saturday to help set up for Will's party. Dean was still a little unsure of Sam's master plan to help him win Holly back but he knew it better be good. While Dean was finishing up grilling, there was a knock at the door and May got up to answer it, "Hello Robert" she said and smiled as she saw Bobby at the door, "its been to long since I had the please of laying eyes on you."

"Miss Mabel you are looking more lovely than ever." He said and kissed her on the cheek as he walked in, "Sorry if I am early. I wasn't sure what traffic would be like."

"It's perfectly fine. This just gives us more time to catch up." May said giving him a flirtatious smile, "The boys are in the back if you want to join them."

"I better go tell them I am here but I will be back." He said and winked at her.

"I will be here." She said and watched him walk off. It was no secret that May and Bobby always had eyes for each other but at their age neither remembered just how to go about doing anything about it.

When Bobby walked out, he say Dean and Sam standing in the back yard next to a flaming grill, "I swear you two idgits can take down any demon but a couple of hamburgers will be the ones to take you down." He said and the guys turned around.

"Hey Bobby." Dean said and walked over to him and gave him a look, "Did you comb your hair?'

"Shut up and tell me where my godson is."

"He is coming with Holly and Jake."

"Jack" Sam corrected and received a look from Dean, "What?"

"Thank you….Sam." he said and turned back to Bobby, "But they should be here soon."

Dean grabbed the plate of burgers and walked into the house leaving Bobby with Sam, "So I am guessing he hasn't won her back yet?"

"Yeah but we are working on it."

"Why he ever let her get away I don't know."

"I think we all know why but I plan on fixing that tonight." Sam said, patted Bobby on the shoulder and walked inside.

After Holly, Jack and Will arrived, Sam grabbed May and pulled her into the kitchen, "Ok I had a plan but I feel kind of bad about it."

"What are you talking about?"

"Well with Jack being here and all. It's kind of mean dont you think?" May looked at Sam and slapped him across the face, "Ouch!"

"Get a grip Sam. After dinner and cake, I will take care of everything." She said and walked out of the room leaving Sam rubbing his face. The woman was one tough lady.

Later on Will blew out the candle and made a wish and like every year, he never told anyone but almost everyone in the room knew what he wanted. May waited until everyone had moved into the living room before going into the kitchen a picking up the phone.

Jack was sitting next to Holly when his phone began to ring, "Hello"

"Mr. Gram I hate to bother you but Mike, uh…Williams jumped bail tonight and we need to you come in to the office."

'Who is this again?"

"Betty Ann, Mr. Stenberg's Assistant."

"Ok well where is he at?"

"He had a meeting with Mr. King and I am unable to get in touch with him and you were the next on the list."

"Ok I will be there in half an hour."

"Thank you sir."

"Who was that?" Holly asked when Jack hung up the phone.

"The office. I am sorry but I have to go take care of something. Forgive me?"

"Of course you go on." She said and gave him a quick kiss as Dean watched. Sam better have something good up him sleeve.

May hung up the phone and when she turned around she saw Bobby standing there, "Well aren't you a sneak one."

"Robert Singer, you know it's not polite to sneak up on people." May said to him.

"So doing a little matchmaking are we?"

"Yeah and what of it?"

"Nothing I am all for it. That boy has been miserable since she left."

"Glad to know you are on board Singer." She said as she patted his shoulder and walked into the living room, "Where did Jack go?" she asked Holly.

"Something came up at work and he had to go."

'That's a shame we were all having such a great time."

"Look what I found." Sam said in a happy singing voice making everyone look up at him. He was holding a small box, "Who wants to watch the best of William Dean Winchester huh?"

"Oh I do." Will said, "I love little me because I am so awesome." Will said and got up to go to the box, "There has to be like ten tape and all of me. Man you guys love me." He said and Holly smiled at him before looking back over at Dean who had an innocent look on his face. Something was up."

"Ok well we can watch a few then we have to go." She said and Sam pulled out the first tape.

"I think we have a winner. Birth Tape." He said and Will gave him a gross look.

"I don't want to see that."

"It's not what you think. You will find this funny." Sam said and smiled at Dean who glared at him, "What it is funny."

Sam popped the tape in and they all sat quietly:

Dean was holding the camera and it was pointed at Holly was breathing heavily walking toward the car, "Ok there is the mother to be looking great."

Holly gave him an evil glare, "Really Dean?" she asked him sarcastically.

"Oh baby you looked beautiful." He said and he watched her get into the car and the camera moved over to the front door, "And here come Uncle Sam." Sam was carrying a bad and was running down the steps when he tripped, "And there goes Uncle Sam. Walk it off Sammy!" Dean yelled and laughed.

"Dean hurry up!" Holly yelled from the car and the camera cut off.

Hospital

Sam was holding the camera as he walked toward Holly's Room and she was breathing frantically while Dean was sitting in the chair next to her looking at the TV, "And here is the happy couple." He said and Dean smiled and waved.

"Oh God I hate you two for doing this." Holly groaned out.

"You will thank us one day when Will is older."

"Well that day is not today so turn the damn thing off!" she yelled and Dean kissed her forehead, "Just act like its not even there."

"Just breath through it Holly." Sam said and he began breathing with her.

"Sam come here." Holly said and Sam walked with the camera over to him. Holly grabbed him by the shirt, causing him to drop the camera onto the floor, "If you don't get out of here I will take that camera and shove it up your ass. Understand?"

"Got it." He picked up the camera and turned it off.

When the Camera turned back on, Sam walked into the room and saw Holly holding Will with Dean sitting next to her, "Is it safe?" Sam asked and she smiled at him.

"Yes Sam. Say hi to your nephew." The camera moved over to the Will who was wearing a blue bonnet and sleeping.

"I was so cute. How could you stand it?" Will said as the tape cut off. He moved over to the next box and pulled out another tape, "What is Dean and Holly's Five Year anniversary trip?" he asked and Holly jumped up.

"We don't need to watch that one. You aren't on it and its boring so let's just move on." She said and grabbed it from him and threw it onto the couch.

"Yeah that's one for later." Dean winked at her and grabbed the tape off the couch, "I will just hang onto this one." He said putting it in his coat and turning to give Holly a wink. She wanted to be mad but she just couldn't when she thought about what was really on that tape.

"Hey mom what about my sixth Christmas?" Will said pulling Holly from her thoughts.

"Uh, yeah that one is fine." She said and looked over at Dean. By the way he was looking at her he had been thinking about the same thinking about.

Will's 6th Christmas

Holly was holding the camera and it was pointed at Dean and Will who were sitting by the tree as Dean handed him another gift, "Alright will show us what you got?" she said and he held up a gun, "Is that…..Dean Winchester! Is that what I think it is?"

"No…..it's just a bb gun. What harm can it do." He said as Will jumped up.

"Dad can we go outside and shoot it please please."

"Of course. That's why I got it." Dean said and got up.

"Dean wait!" Holly yelled putting down the camera and going after them.

Sam saw the camera and walked over to it, "We don't need to miss this one." He said and picked up the camera and walked outside and saw Dean and Holly and zoomed in closer.

"Dean he is six years old. Don't you think that's a little young?"

"What are you talking about? I got a real one at five and look how awesome I turned out."

"That was different."

"Holly relax, nothing bad is going to…..SON OF A BITCH!" Dean yelled and grabbed his leg. And Sam moved the camera to see Will laughing with the gun pointed.

"What were you saying Dean?" Holly said and went over to Will and took the gun.

"Walk it off Dad." Will said and the camera was shaking from Sam's laughing so hard.

"Sam cut that damn thing off and help me!" Dean said and the camera went to static.

Holly was sitting on the couch laughing so hard the tears were coming down her face, "It wasn't funny. That shit hurt." Dean said

"Yes….yes it was." Holly said as she contused to laugh.

"I still have a mark on my leg form that."

"Well maybe next time you will listen to me." Holly said and didn't realize what I came from her mouth at first.

"Next time?" Dean asked.

Holly wiped her eyes, "You know when it comes to buying Will something. Ok what's next?"

"Dad's birthday." Will said and put in the tape. Everybody made their own recording that day wishing Dean a happy birthday. It was also his last birthday before the deal.

Will

Hey Dad it's me the best thing to ever happen to you. Yeah that's me. I just want to say man you are getting old but it's ago so is the impala but like you said, things get cool as they get older and you are still a very cool dad so Happy Birthday.

Bobby

Well looks like you can drop the old joke because you are not far from me now you idgit. Happy Birthday Dean. Your Daddy would be proud of you.

Sam

Hey Dean uh well I will try not to be too sappy because that just mean I won't ever live it down once you see this so I just want you to know that you are the best big brother anyone could ask for and there is nothing I wouldn't do for you. I hope you have a Happy Birthday.

Holly sat there on the couch for a minute and she new exactly who was next and she didn't know if she could take it. Not now.

Holly

Hey sweetie it me as you can obviously see. Will wanted to do this for you so here I am and you know I hate camera. But you remember that from our anniversary a few years ago but I made it though that so here goes nothing. I Love You so much and you are a great husband and father. What else can I say but no matter what happens you will always be my hero. I love you Dean always and forever.

Holly got up from the couch and walked out the back door, "I'll go check on her." Dean said and got up.

"Hey Uncle Sam find the one of us singing karaoke" Will said and Sam smiled ay him.

Holly walked out into the back yard and looked up at the shy with tears in her eyes, "Are you ok?" Dean asked as he walked up behind her.

"What was all this Dean?" she turned and asked him.

"What are you talking about?"

"The tapes."

"Hey I didn't do that. That was all Sam's idea but why does it matter. Afraid certain feeling will show up?" he asked and leaned against the railing.

"You don't get it Dean."

"Get What Holly?"

She just sighed and tried her best to stop from crying and running over to him no matter how much deep down she wanted to. "I never stopped loving you Dean. That is not why I wanted the divorce."

"Then why did you because honestly I would love to know."

"Because you didn't love me Dean. At least not they way you use to. I was always ok with beginning the second thing that was most important to you .hell I was ok with third but Dean the thing that broke my heart the most was….was when by the end I didn't even make the list."

"How can you stand there and say that? I have done everything for you and Will."

"Like selling your soul? Was that for me or Will?"

"You know why I did that!" Dean raised his voice. She knew he had to save Sam.

"Yeah I do but guess who had to bury you Dean...that was me. I saw you ripped apart and I buried my husband who promised to be around forever. Then four months later only to have you come back from hell of all places and wait two fucking day to tell me about it. I just...Dean I couldn't do it anymore but I would be lying if I said that I didn't wish that one day you would come back for me but its two years too late Dean. I am with Jack now and he loves me and I love him. I owe it to myself to try and be happy."

Dean looked at her and he wanted to say I don't want you to be happy I want you to be with me but he could do that. He wanted her to be happy just with him. He knew he had to let her go. He owed it to her after everything she has done for him, "You're right Holly. You should be happy and if Jack is what you want then there is nothing I can do to change your mind. I was selfish and cocky. I never thought I would ever really lose you because in the past you were always there no matter what happened. We fought a lot but I was never worried because I knew that I loved you. I am sorry I never showed you but it's the truth. You were number one on my list for the first moment I saw you. Then it was Will but I guess you can understand that. I have regrets and a lot of them but you were never one of them. I just took what we had for granted and I am sorry for that. I want nothing more than for you to be happy and if that means letting you go then I am willing to do that." He said and turned and walked into the door leaving Holly standing outside in the cold with her mascara running down her face.

She walked over to her car and got inside and reached into the ash tray and pulled out her wedding band and began to cry even harder. Why did he have to say those things to her now of all times?

Holly looked down at her left hand and saw her engagement ring as she held her wedding band in the other. Getting married was supposed to be the easier decision of her life and it was the first time. Why was she now thinking the second time wasn't as easy as she though it was? She had a decision to make and it was one that would change the rest of her life. Was she meant to be with Jack or was it Dean she belonged with? She just now had to take time for herself to figure out what she truley wanted.

A/N: ok guys that was a long chapter for you. Two chapters in one day wow. Also thank you DeanWinchester GuardianAngel for helping me out with this chapter. Also we are making the contents of Dean and Holly tape a one shot on our page in the story Dude you stick like sex. Anyway please review you guys and I will work on the next one. It will be an fb of Dean and Holly in the beginning. So if you want it please review! Love you guys and thanks again for voting!