Destiel One-shots

Bobby Singer

Bobby Singer may not have been the Winchester's biological father, but he knew a lot more about them then John did.

Bobby was the first person Dean came out to, when he was only fifteen. Bobby accepted him immediately, unlike John.

But Dean cared more about John's opinion at that time, and was crushed. He didn't even tell Sam, for he was so ashamed. The moose didn't find out until Dean died, and Bobby had secretly told him. 

Bobby Singer was the only person there to witness Dean and Castiel's first meeting, and he knew the look in the Winchester boy's eyes after he found out Castiel wasn't a threat.

Bobby Singer knew Dean had a crush before Dean himself knew. 

And Bobby, although he didn't know squat about angels, he could tell a little piece of Castiel was pining for Dean, even if he wasn't supposed to.

Bobby secretly asked Crowley about it, and the king of hell did admit that it was a growing piece of gossip amongst the afterlife.

Bobby was the first person who shipped Destiel, even before Sam did.

Bobby was the one who'd sigh every time they'd stare at each other, wishing Dean would grow a pair and make a move. He never had a problem flirting with girls- why was this any different?

Bobby thought that maybe, if he had been Dean's real father, the boy might've felt more confident with himself. But he couldn't change that.

Bobby was the one who, in that split second after Cas was exploded as the apocalypse went down, was furious that Dean would never be able to find any happiness with the angel. Imagine his relief when Cas came back, good as new.

Bobby Singer knew how badly Dean and Castiel were in love with each other, and how much seeing Dean with Lisa hurt the angel.

Bobby Singer would have quiet talks with Cas about Dean, sharing funny stories, and explaining to the angel why Dean didn't talk about his feelings.

Bobby Singer also had talks with Dean, when Sam was out of the room. Those talks were the only time Dean felt he could really be himself.

When the Leviathans were released, and Dean pulled Cas's coat out of the water, Bobby saw how heartbroken the Winchester was. He later saw the relief in his eyes when Cas came back.

Bobby Singer died, wishing he could've done more to nudge the boys together.

When he came back as a spirit,  Bobby told Dean everything. Everything he'd been thinking, everything he knew Dean and Castiel could be.

Dean listened, but only acted in the bare minimum way he could.

When Dean told Cas he needed him, Castiel knew what he really meant, because Bobby Singer had told him.

When Cas said he loved them all, he was telling the truth, but he and Dean both knew the words were meant just for Dean. Dean knew because of what Bobby had told him. 

Sometimes, Cas would go up to heaven, and let Bobby watch what was going on with the boys. He liked that. He liked knowing how they were doing, making sure they were okay.

But the angels were a bit concerned about Bobby Singer on the day that Castiel and Dean Winchester got married.

The dead hunter was screaming and freaking out for hours afterwards. According to another human source, Bobby wasn't panicking. He was fangirling, for his ship had sailed.

Bobby Singer was the first to ship Destiel. 

And maybe, just maybe, he's the reason it finally sailed.