Thanks to Soar for the beta and Soar, JuliaAurelia, and Sinead-Conlan for their feedback.

Disclaimer: Still don't own,

Regret

1991

John Winchester pulled his shiny, black, classic '67 Chevy Impala into the driveway of Singer Salvage. He was just returning from a meeting with Mrs. Pratt, Dean's sixth grade teacher.

His 12 year old son had been injured on a hunt during the school year, and the broken rib hadn't seemed serious until it had punctured Dean's lung. It hadn't healed properly and Dean had ended up needing surgery, which had resulted in pneumonia. John shuddered as he recalled that they had nearly lost him a couple of times during the whole ordeal.

The whole thing had caused Dean to miss a great deal of school. He had been struggling that year to begin with, so the prolonged absence hadn't helped matters, and John had been called in for a parent teacher conference, where Mrs. Pratt had informed John that she felt it best if Dean repeated the 6th grade.

John wanted to refuse. He had friends that could easily doctor Dean's records, and John would have no problem enrolling him in the seventh grade in whatever town they settled in next, but Dean still wasn't 100 recovered, so John did not want him to spend the summer hunting.

John debated what would be a bigger blow to Dean's ego, repeating 6th grade, or going into 7th and not being able to keep up. In the end though, he had agreed to the teacher's request. Telling Dean this was going to be so much fun.

Shaking himself out of his thoughts, John got out of the car and entered the house. He went straight to the kitchen, looking for a beer.

"How'd it go?" Bobby inquired.

"About how I expected it. Mrs. Pratt feels it would be better if Dean stayed back."

"You know that it's not his..." Bobby said, quick to defend John's eldest son.

"I know it's not his fault. He just missed way too many days. It's not surprising he was held back," John agreed.

"Make sure you tell him that, Johnny," Bobby cautioned. He could tell something else was bothering his friend. "What's wrong?"

"Mrs. Pratt thinks Dean may have a learning disability. She wants to have him tested for dyslexia this summer. She thinks that's why he's been struggling all year."

"Are you going to?" Bobby asked.

"I don't know."

"Why don't you leave the boys with me for the school year? Sam has made some good friends and it would give Dean some stability. You could use this as a home base," Bobby offered gruffly.

"I did want to go after that coven," John mused aloud as he considered Bobby's offer. "It would be too dangerous to take the boys."

Maybe you should stay and support your son. Not wanting to start anything, Bobby just said, "Yeah, if they find your weak spot, Sam and Dean could be targets."

"I know," John agreed. "It makes sense, and Dean can get his tests. Mrs. Pratt said that he's really getting down on himself and starting to think he's stupid."

"He's not," Bobby said.

"I know that," John agreed. "Mary would be so disappointed in me for not noticing this. Education was important to her, and she would have caught the reason for Dean's struggles right away." John sighed. He was not looking forward to the up coming conversation with his eldest.

"He's in the yard with Sammy," Bobby said, knowing it was best to get it over with.

What John and Bobby didn't see was the young, blond haired boy that had been standing outside the kitchen door. Sammy had been thirsty and Dean had gone to get him a drink. He found his father and Bobby in the kitchen and heard the words, 'repeat 6th grade.' The words had frozen him to the spot. The problem was that the door was thick and there was a radio playing, so Dean could only hear snatches of the conversation.

'Expected it... Dean should stay back... struggling all year... Dean's tests... he's stupid... Mary would be so disappointed.'

Dean felt tears sting his eyes. Did his dad really feel that way about him? He could hear Bobby tell John that he was in the yard, so he quickly took off, so his dad wouldn't know he had been eavesdropping. He had been warned about that several times.

Dean was in a foul mood when John found him, and he wouldn't listen to a thing John had to say. John had ended up getting frustrated and yelling at Dean that repeating 6th grade was an order.

--

2005

John stepped out of the shower and quickly dried himself off. He was in a really foul mood. It had been five days since he and Sam had the big fight, and his youngest had stormed out the door and hadn't looked back. It was typical of Sam that the only order he had obeyed in the last several years, without argument, was the one that John had never meant to give.

John seriously regretted everything he had said, but in typical fashion, stubborn Winchester pride had kicked in and John wouldn't admit that he had been wrong. Then, staying true to the pattern, John's wounded pride turned to anger, taking it out on the closest source, his eldest son.

After Sam had left, Dean had become quiet, as he often did when things started piling up on him. John figured that the best way to deal with the situation was to get right back into the hunt.

They had found what looked like a typical spirit, haunting and terrorizing a town. It should have been a routine salt and burn but, of course, it didn't turn out that way.

John had put Dean in charge of the research, as he hated it even more than his eldest did, and he went to interview the victims' families. John operated on a need to know basis, and when he received a piece of information that he didn't feel was relevant to the case, he had failed to pass it on to his son. Dean, not used to questioning his father, like Sam would have done, accepted that and he quickly found a pattern that seemed to make sense and John agreed, so they went to the cemetary. Of course, that little piece of information was vital, and things quickly went south when John and Dean realized that they were digging up the wrong grave.

Fortunately, they both escaped with only minor injuries. John had some cuts and bruises and Dean had a nasty gash on his arm that was going to require stitches.

They returned to the motel, with John berating Dean the whole way. When they got back to their room, being the eldest, John called dibs on the shower and when his father came out, Dean took his own turn, hoping that his father hadn't used up all the hot water.

While his son was showering, John went looking for the first aid kit so he could suture Dean's arm. The last time he remembered seeing it, was when Dean had stitched up Sam's leg, when he had been swiped by a black dog.

Spotting his son's duffle bag on the bed, John opened it and pulled out the suture kit. Dean's bag had been perched on the edge of the bed and when John set it back down, it rolled off. A few of Dean's shirts fell out, as well as a small box that John had seen on occasion. When John had asked his son what was in it, Dean had replied that it was stuff he needed and refused to say anymore. John, not thinking it was important, had let it go.

When the box had landed, its lid had popped open, spilling its contents. John tried not to look as he picked it up, but his curiousity got the better of him. There were several photographs of the Winchesters and Bobby, and even one of Mary. John put that one away quickly. There was also Sam's acceptance letter to Stanford. John put that away in a hurry as well, surprised that Dean had kept it. There was a small notebook that contained women's phone numbers and John smiled at that. John also smiled when he saw the Purple Heart that he had received in Vietnam. John remembered giving it to Dean after he had beaten the pneumonia that almost claimed his life. He remembered the smile Dean had given him after he handed it to his son. He saw a few report cards, and was surprised that Dean had kept them. He had the last thing in his hand when he heard a voice behind him.

"What the hell are you doing?" the voice demanded.

--

Dean finished his shower, looking forward to a cold beer and a hot bacon cheeseburger. All thoughts of food flew out of his head, though, when he saw his father going through his box. He was immediately angry at his father for violating his privacy.

"What the hell are you doing?"

He watched as his father turned around and looked at him sheepishly. John, at least, had the good grace to look embarrassed. "It's not what it looks like, Dean. I was looking for the first aid kit and it fell out."

Dean quickly closed the gap between himself and his father. He wanted his box back. Dean realized that his father hadn't looked at the envelope in his hand yet, he and really wanted to keep it that way.

"Just give it back," he requested.

"Here," John said handing it over, and Dean froze in mid stretch when he saw his father glance at the front of the envelope.

--

John looked down and saw the logo in the corner that said Massachusetts Institute of Technology. It was an even bigger shock when he saw that the letter had been addressed to his eldest son.

"What the hell is this?'

"Dad, I..." Dean started and then stopped, not knowing what to say.

"You were going to leave your brother?" John snapped. "You got so upset when Sam left and you were going to do the same thing."

"I wasn't, dad. I wasn't going..."

"Why? Didn't get in?" John said harshly.

Dean tried to bury the hurt that washed over him. "No," he said. "I just... My guidance counsellor suggested it. He kept bugging me. I did it to get him off my back," Dean said and his eyes dropped toward the ground as if the pea green carpet was the most interesting thing he had ever seen.

John knew that there was much more to the story. Dean wouldn't make eye contract which was one of his tells. "Did you want to go?" he asked.

"No, dad. I swear," Dean insisted as he finally raised his eyes to John's. "I just wanted to um… I just did it for fun."

"Why MIT?" John asked curiously, his anger abating slightly in the face of Dean's earnestness.

"You always said go big or go home. I figured if I was going to apply, why not go for the top," Dean said.

"So this was a joke?"

"Yes sir," Dean said, desperately hoping that his father believed him and would drop the subject.

"Why would you keep a rejection letter?" John said unthinkingly.

"Did you read it?" Dean asked.

"No," John admitted.

"Why would you automatically assume I didn't get in?" Dean said trying to keep the hurt out of his voice.

John didn't miss it. Did that mean Dean got accepted? "You got in?"

"I uh, um… I don't know," Dean said softly.

John took a second look at the envelope in his hand. That's when he realized that it had never been opened. "How come you never opened it?" John's curiousity was growing.

"No intention of going, so why bother," Dean said with a shrug.

"I'll get rid of it then," John said as he walked over to the garbage can and held the envelope over it.

"No," Dean cried. "It's mine, give it back."

Dean suddenly sounded so young to John's ears. He really wanted to know why his son was so upset over this. He was starting to regret his earlier words, as it occured to him that they might have had something to do with Dean's current mood. Contrary to popular belief, John hated it when his boys were hurting.

John pulled the letter back, but he still refused to return it. "Tell me what this is about, Dean."

"I told you," Dean said firmly.

"I want the truth," John said trying to soften his tone, but keeping it firm at the same time.

"I guess I just wanted to prove..." Dean stopped abruptly, his face suddenly losing all expression. "I did it for fun," he reiterated.

John frowned. "Prove what, Dean?"

"Nothing," Dean insisted. "I'm hungry. Are you hungry? I can go get us some food."

"You're not changing the subject. What did you want to prove, Dean?" John asked again.

"I told you… nothing. Can't you just leave it alone?"

"No," John said stubbornly. "What did you feel you needed to prove and to who? I want an answer and it's an order, Dean."

Dean sighed in resignation. "I, uh, wanted, um yo... Nothing," Dean tried and eyed the door, mentally calculating his odds of escape.

"Me," John said in surprise. "What did you have to prove to me? Talk to me. What is it about this letter?"

"Please, dad, don't. Leave it alone." Dean tried to bolt past his father, but John quickly grabbed him.

"Tell me what's going on."

"I... I just… it's nothing."

"Dean, it's a simple question."

That was the wrong thing to say. "What? Am I too stupid to answer it? Is that what you're saying?" Dean snapped.

That was the last thing John had been expecting. "What...What are you talking about?" John stammered.

Dean cut him off, he couldn't help himself. "You think I'm stupid. I heard you."

"Dean, what the hell are you talking about? Is that what this letter was about?" John asked as the pieces fit together for him. "You thought it would prove to me that you weren't stupid. I never thought that. Why would you think that?"

"I heard you," Dean said sadly, all fight draining out of him. "I heard you tell Bobby after my teacher told you I should repeat 6th grade."

"Dean, I never said you were stupid."

"You told Bobby you weren't surprised I was struggling with my tests because I was stupid and you..." Dean paused, trying to force his emotions back down. "You said that mom would be so disappointed in me because she was a teacher."

John was floored by that admission. "I never said that," John replied feeling awful. Dean must have overheard parts of the conversation he had had with Bobby years ago and misinterpreted it.

"Stop lying. You did," Dean said. He was mad at himself for losing control and it was starting to creep into his tone.

"You didn't hear the whole conversation, son," John replied gently and in disbelief that Dean had been carrying that around with him for the last 13 years. "I told Bobby that I wasn't surprised you were held back because of the amount of time you missed, and that your teacher thought you were struggling with your tests because you had a learning disability, and she was concerned that youwere starting to think you were stupid."

"But you were mad at me for failing. You dumped me at Bobby's," Dean accused.

"I didn't dump you at Bobby's. You still weren't fully recovered. I wanted you to stay in one school until you caught up and I was going after a witches' coven. I knew you and your brother would be safe at Bobby's. About your mother..." John paused. "When I said she would be disappointed, I never said she would be disappointed in you. She would have been disappointed in me for not taking your education seriously, and paying attention to the fact that you were struggling. She would have caught your dyslexia right away. You never had to prove to me that you were smart, Dean. I know that."

"Why did you automatically assume I didn't get in then?"

John really didn't have an answer to that. "I guess it was just easier to assume you didn't, not because I didn't think you were capable, but because you didn't leave."

Dean could clearly hear the words 'Like Sammy.'

I would never leave you and Sammy. "I wouldn't have gone, dad, even then," Dean said.

"I know. Forgive me?"

"Can I remind you of this in the future if I screw up?" Dean asked with an evil grin.

"No," John said firmly. "This never happed. Can I ask you one more thing?"

"No, but I know you're going to anyway, so go ahead," Dean sighed.

"How come you never opened this?" John said gesturing to the envelope.

"In case they said no, I didn't want to disappoint you again," Dean said timidly and lowered his gaze.

John shook his head. "You couldn't ever do that, Dean," John said softly. "Want to see what it says?"

"No," Dean said quickly and reached for it. "I'd rather not know."

"Can I look?" John asked.

"I..." Dean wasn't sure how to phrase his request. He didn't want his dad to open the envelope.

"Okay, I'll make you a deal. Let me hold on to it and when you're ready, we'll open it," John offered.

Dean didn't really want to because he had a feeling that his dad would open it when he wasn't around, but he couldn't say no to his dad. "Okay," he said reluctantly.

John had every intention of opening the letter when Dean left to go pick up dinner, but for some reason, he found he couldn't. He knew that Dean didn't want him to and he had already hurt his son enough.

--

John kept that promise for the next three and a half years. Until the night he sat in the cab of his truck and watched Dean enter Sam's apartment building. He knew that he had hurt his son again by disappearing, but he had to, to keep him safe. He had hoped that Dean would go to Stanford and get Sam.

As he watched his eldest disappear from view, he reached over and grabbed the MIT envelope out of his dash, he had never had it far from him since he'd taken possession of it. For reasons he couldn't explain, he couldn't resist any longer, so he opened the letter and read it.

His chest constricted as he laid Dean's letter on the seat next to the copy of Sam's that he had, and he put his keys in the ignition and pulled away. His thoughts were on what might have been. The life his boys could have had, should have had. The life his boys deserved, but would probably never have.

--

Dear Mr. Winchester,

Thank you for your application to the Massachusetts Instituteof Technology. We are pleased to inform you of your acceptance into the mechanical engineering program for the fall semester.

Your final acceptance is conditional upon the receipt of your final high school transcript, showing successful completion of your current course load.

Please send confirmationof your desire to attend and if you are seeking housing on campus, as soon as possible, since space is limited.

If you have any questions, please feel free to contact the admissions office at 1-800-555-5865.

Thank you for making MIT your school of choice and we look forward to having you as a student next fall.

Sincerely

Derek Fitzsimmons

Executive Director

MIT Admissions.

A/N: Please remember to read and review. Even one makes me happy.