He had a habit of getting into quite the sticky situations, especially when he wasn’t with Sam.

Dean was not his best when he wasn’t hunting with his brother. Them constantly having fights and nagging all the time would bring anger onto Deans mind, causing him to slip up faster than a demon during interrogation.

It was his fault, really. He knew he should have waited for Bobby to call with the proper way to kill whatever he was after, which happen to be an amped up werewolf.

Dean knew he was fucked the second his gun with the silver bullets got knocked from his hand and slid all the way across the room. Oh, he knew he was extra fucked. But, due to Deans scatter brain he didn’t think to get any sort of backup weapon.

He suffered a good beating and a long drawn out endless battle that unfortunately ended with him being flown across the room into the wall.

His eyes slowly opened, coughing. Dean was dizzy and disoriented as he slowly tried to sit up to look around.

To his amazement, the fuckin’ asshole werewolf was knocked to the ground and dead with none other than you standing above the body holding your pistol.

“Jesus—…” He muttered, his eyes scanning you up and down before he leaned back against the wall with a heavy sigh. “Thanks, I owe you one…”

Hell yeah he does.