Supernatural Oneshots | ✓

The Art of Breaking It {Dean}

Prompt inspiration: 642 Tiny Things to Write About by The San Francisco Writers' Grotto

Prompt: Write about a time you broke: a bone, a heart, the law, a promise.

Summary/prompt change: There are four main things you could break that are actually important. Dean Winchester knows too much about all of them.

"So, Mr. Winchester," you said, filling up Dean's cup. Truth or Dare with the Winchesters? Talk about interesting. Especially with some alcohol in them. They're more willing to be honest when they're drunk. "Truth? Or dare?"

"Truth." Dean said with a laugh. "I know where dare's going to get me with you."

"Smart boy," you said. You tilted your head to the side, carefully considering. "How many of the four have you broken, and what were the situations in which you broke them?"

Well, it was a good way to get to know them–you'd met the Winchester boys two days ago in a bar. You and Dean started talking, and next thing you know you're in their shitty motel room on the floor between the beds, a few bottles of cheap whiskey and tequila and three cups between you.

"The four?" Dean asked. "What are the four? Four what?"

"You've never heard of the four?" You sipped your drink and set your cup down on the stained carpet. "The four are like, the main four things that are breakable that actually matter. They're a bone, the law, a promise, and a heart."

Sam cringed. "That sounds fitting."

Dean let out a sigh and set down his cup. "How many and what happened, right?" You nodded, and he scratched the back of his neck. "And if I've done it multiple times?"

You were taken aback, but you tried to recover. "Um, then you say the most important one? I don't know. I've never heard of anyone doing any of the things multiple times."

"Well, let's see. I've broken my collar bone a few times. Can't exactly remember how, but it hurts like a bitch. I've broken the law more times than I can count, but there was one time Sammy and I posed as Homeland Security that really would've gotten us into trouble."

You let out a low whistle. "Homeland Security? Man, you guys better hope nobody ever puts warrants out for your arrests, with records of things like that."

Dean shrugged. "Never got caught. What were the other two?"

"A promise and a heart."

"Right. Well, I promised myself I'd never go back to the house Mom died in. Did that."

You tilted your head to the side. "Your mom died?"

"In my nursery." Sam said. "Fire."

You cringed. "Sorry."

"It was a long time ago." Dean said. "And I've moved on."

You could tell that it was still a sore topic, no matter what he said, but you didn't say anything. "Okay. And a heart?"

"Too many." Dean said. "But I can think of one that's going to happen very soon." His eyes were heavy on you, and maybe it was the alcohol, but you swore he looked a little regretful. He took a swig of his drink and looked at Sam. "Truth or dare?"

"Um..." Sam looked between you and Dean. "Dare?"

Dean nodded. "Okay. Get out."

"I–what?"

"Go. There's your dare. See you later."

Sam stood up, still looking confused. He half-walked-half-stumbled from the room, the door slamming shut behind him.

"Well," you said. "That was rude."

Dean shrugged. "He's got the keys. He'll fall asleep out there." He suddenly didn't look so drunk. "I'm really going to hate leaving here." His eyes kept darting down to your lips.

"You could always stay." Was it hot in there, or was it just him? No, that was wrong. It was supposed to be or was it just you, but you technically weren't wrong...

Dean shook his head. "I can't. Thanks for the offer, though." He took a deep breath. "You're into me, aren't you? Tell me that I haven't been reading you totally wrong." It sounded like a plea.

"You haven't been." You said. "And I would assume you're asking either because you're going to let me down gently, or you're going to try and push a little farther than this awkward eye contact bullshit."

"Smart girl," he said. "Truth or dare?"

"Really, Dean? I–"

"One or the other, sweetheart."

You glared at him. "Dare."

Dean swallowed hard. He licked his lips like he was trying to put off talking for as long as he could. "Give me tonight?"

"Sam's going to kill you."

"I don't care."

"He's going to kill me, too."

Dean shook his head. "Nah. He's too nice for that." He leaned forward and pressed his lips to yours.

The problem was that Dean Winchester's prediction during that game was completely accurate. Less than a week later, he and his brother fled town. And when they did, they left you and a cracked heart behind.