30+ Days of Team Free Will Imagines

Day Six

Prompt: Imagine being someone who was really important to Dean, but went missing and was found dead before the Pilot in Season One, and whome Dean occasionally mentions as "somebody he knew who used to..." Sam finally asks him who you were and Dean goes quiet because he still misses the shit outta you.

Tags: Female!Reader, Psychic!Reader, Reader/Dean Winchester, Dead!Reader

Note: Y/B= Your Birthdate

......

"Why don't blind people go skydiving?"

"Why?"

"Because it scares the crap out of the dog!"

Dean laughs, head thrown back against the cheap motel couch. "Aw, man," he sighs, taking a swig of his eggnog and gazing across the room at the frankly pathetic tree Sam put up, decorated with air fresheners and bobbers. "There was somebody I knew who used to..." he trails off, suddenly caught up in a memory.

Sam nudges him, knocking his brother out of memory lane. "Used to what, Dean?" he asks.

"Oh, they used to tell this joke," Dean says, trying to act as if he hadn't just zoned out. "All the time, actually, so everyone knew it already. It goes like this: a grasshopper walks into a bar. The bartender says, 'Hey, we've got a drink named after you.' The grasshopper is confused and says, 'You have a drink named Steve?'"

Sam cracks up. "I wish I could've met them," he says when he's calmed down. "They sound like a riot."

"Yeah," Dean says softly. "They were."

XXXXXX

Dean doesn't mention this "somebody he used to know" often, but he always gets very quiet after he does. Sam isn't blind or stupid. He notices. It's hard not to.

It bothers Sam, in a way. After all, he's know the man his whole life. He knows everything there is to know about Dean- at least, he thought he did. Now, he's not so sure.

Every time Dean mentions this somebody, Sam wants to ask. Who are they? What happened to them? But it never feels right. Someday, though, he'll ask.

Someday.

XXXXXX

The next time Dean mentions the somebody, Sam decides to just go for it.

"Dean?" he says, pulling his brother from his thoughts.

"Yeah?"

"You always talk about this person you used to know. Who are they?"

Dean is very quiet for a long time, only the sound of the Impala's engine breaking the silence.

"Y/N," he says finally.

"Was she a hunter?"

Dean shakes his head. "No. She was a psychic. Not just any psychic, either. She was up there with Missouri and Pamela. Hunters came to her for help on hunts, but she never fought. She was so gentle. Wouldn't hurt a fly, really."

"What happened to her?"

His brother shakes his head. "You don't want to know."

"Tell me, please."

"She's dead, Sam. What else is there to say?"

Sam studies Dean a moment before saying, "You loved her."

Dean bites his lip and says, very quiet, "Yes."

XXXXXX

"Do you have to go?" you ask, clinging to the man. Your sweet Southern drawl is more prominent in response to your distress.