Sure, Dean died multiple times, in many different ways, but he got used to it at some point.

Death? Tsk, he’d be back in a few hours. Or even less.

However, he didn’t tell anyone, Sam or Cas, who he was seeing during his stay in between the mortal world and whatever else was waiting for him. Every time his heart stopped, as soon as he’d open his eyes, a familiar face hovered over him with a small, kind smile. Every single time it was the same grim reaper keeping him company. Not even collecting him as it was supposed to happen — you’d just stay with him and keep him company until he got brought back to life. ‘Cause everyone knew the deal with the Winchester brothers.

They just couldn’t stay dead for long.

You walked through a small alley, your hands in the pockets of a long, black coat you were wearing. Your steps echoed within the walls until you finally stopped and everything had gone silent. Tilting your head to the side, you smiled at the man as he slowly opened his eyes.

"Hey, handsome,” you said, waving your fingers when he finally looked up at you. With a groan, he slowly stretched his back, getting up on his feet.

“Yeah, good to see you, too,” he muttered, holding his side as he looked around. It was empty, just you and him, and the scenery he saw last before dying.

“What was it this time?” you asked, wiping some rain droplets from his cheek. He had a slight stubble, something new compared to the last time you’d seen him. Dean chuckled and shook his head, sighing loudly.

“Demons, obviously. Nasty fuckers,” he scoffed, looking to the side, probably in the direction where his killer had gone. But he quickly cleared his throat and averted his eyes on you. “Doesn’t matter. I just know you were happily rubbing your lil’ skeleton hands, knowing you’re about to collect my soul,” he snarled, but his hands found their way around your waist, and he pulled you closer towards his body.