This is part of my Bobby shouldn't be killed off set. Bobby should live long and proud or I'm going after someone with a pitchfork. Comment if you support a living Bobby.
Bobby Singer never had children life had torn his wife away from him before he had the chance. It would seem a bit cliché but she was the only woman Bobby would really love. So when a couple of years went by Bobby had never found another woman to take his interest and then John Winchester showed up with two little boys in tow.
So after a few years if you asked Bobby if he had sons he could still say no. Or he could say yes cause in way Sam and Dean Winchester were his sons.
Sam and Dean were grown men. They'd seen hell more times then they wanted to. They'd lost each other over a dozen times more then they'd ever wanted to. They'd never had a real home as boys. Their father had dragged them from hunt to hunt, state to state, from one end of the country to another.
Sam and Dean Winchester never truly got to be boys growing up and it showed in their mindless bits of banter and silly wrestling fights they had.
Bobby Singer who'd known these two since they were five and one was the closest thing to home they ever had and Bobby was the closest thing to a father they ever had. True they had a father growing up but to him his sons were more like soldiers and it showed. Bobby saw it many times when John was speaking to Dean the boy stood tall with a straight back as his father talked.
Dean always answered "Yes sir." or "No Sir."
John had a habit of leaving them while they were growing up in different motels to go on a hunt. Dean was always told to look after his little brother. Even though they were two energetic little demons Bobby would rather face them then the ones with black eyes. He loved those boys like they were his own.
So many times when John was close enough he would show up with a shy drawn back look asking to leave the boys and Bobby would accept. Those kids had wormed their way into his heart. The Bobby had tried to so hard to freeze after the loss of his wife. That didn't happen.
So years went by things happened and it would be years before Bobby saw either boy again. Last he'd seen Sam the boy had been seventeen and a gangly youth as tall as his brother with no more baby fat to speak of. Dean was a grown man now at twenty-one. They hadn't seen it but Bobby and John had a falling out like no other. He had the gun cocked and everything.
Something about Sam trying to do the best to could to get into a good college. John didn't want him to go. That was it for Bobby. Any father should be proud that his son would try so hard to go to a good college, have some bit of normalcy in his life. But no John Winchester was a son of bitch and a pain in the ass and that was the last time her saw him.
But when he saw the boys again he couldn't believe what he saw. Sam at 22 was back on the road with his brother looking for their father after just losing his girlfriend. He was taller then Dean now and the two were all business.
They left with the promise of returning and when they did they were somber faced and grieving for their father.
Now they had a chance to relax a bit and that was always a good thing. The apocalypse was over Sam had his soul and Dean had his brother and Bobby had his boys back under his roof where they could enjoy some normalcy in their lives.
"Get off me you idiot." Was followed by a loud crash in the other room followed by laughing. They were wrestling again something they didn't get to do much when they were boys. So Bobby allowed it for a few moments. It was a tickle fight and Sam was losing badly.
"You boys go get washed up for dinner." The old hunter had told them.
Dean got off his brother but fell over when Sam grabbed his ankle pulling him to the floor and jetting ahead of him.
"Idjits."
When they came back down stairs wet in various places Bobby didn't see two grown men. He was two boys ages 12 and 8 about to sit down to dinner. If they ever needed it he would be there for them with open arms and some bit of normalcy in their lives of killing supernatural creatures, saving lives and living on the road.
"Thanks Bobby." The two chorused.
"You're welcome boys."
So did Bobby Singer have children?
Answer: Yes.