#reader gender unspecified

His laugh was a little uncomfortable and he glanced back down at his book. “We both know that’s not true. Out of the two of us, who hasn’t been addicted to demon blood?”  You felt a pang in your heart for him and decided to deflect back toward lighter conversation. “Did you just call me perfect?” you joked. His eyes met yours again and they were soft. It sent a zip of electricity up your spine. “Something like that.” You felt your cheeks growing warm with a blush and had to tear your eyes away from him. “I’m trying to work over here, Winchester. If you keep distracting me we will never get anything done.” He laughed easily. “Alright. But promise you’ll tell me as soon as you need a break so I know when it’s alright for me to compliment you again.”

*instantly changes it to something neutral*

Reader gender: unspecified “Are you insane?” you asked him in a flabbergasted whisper. “You’re literally the Devil!” “That’s exactly why it would be so incredible! Come oooon! You don’t belong in this group of deadbeats! Think about it. Just you and me. World domination. And, I promise, a lot of really delicious sex.” He bit his bottom lip and may no effort to hide the look he gave you up and down. You scoffed at him and crossed your arms over your chest. “The only reason we are working with you is because we have no other choice. So, I would suggest you stop daydreaming and start trying to give a shit about something that actually matters.” You started to walk away but spun around just a few steps from him. “And those deadbeats? They’re my family. I hope you’ll remember that.” Happy Supporting Character Saturday!!

reader gender: unspecified Dean was talking with Cas, brainstorming the next step in their plan to avert disaster when a dreamy expression crossed his face and his blue eyes suddenly focused on something over Dean’s shoulder. The Winchesters knew, of course, that you would be there, but Cas had no idea. He thought you were still across the country, so the sight of you sent his heart soaring and lifted his spirits. He didn’t hear a word Dean had said. The angel’s face lit with a smile and you couldn’t help grinning at him. He pushed around Dean, carelessly bumping into him as he crossed the space to get to you. “Y/N.” He was shaking his head a little in disbelief. “It’s so wonderful to see you. I thought--I thought you were away until next month.” You shrugged a little bashfully and felt too shy to continue to hold his eyes, so you stared down at your feet. “Well, that just felt too long...” “It did,” Cas eagerly agreed. “It really did.”

“You wanna talk about it? You’ve just been... I don’t know--defeated lately. It’s not like you,” you said. Dean sighed heavily and finally looked over at you, meeting your eyes for the first time since you sat down. “It’s just... everything. Sometimes I feel like all these fights,” he shook his head, “I don’t know. You finish one and there is always another one. And another one. And another. And we have managed so far to scrape by and somehow pull off some kind of win but we can’t do that forever. At some point, we’ll lose. It just feels futile. And I’m just tired.” “You’re right. There is always another fight. But the important thing is that we do fight. We can’t just give in. Think of all the people you’ve saved. Hold onto that.” He sighed again, but this time it was less weighty. And eventually he nodded. “You’re right. Of course you’re right.” You nudged him a little with your elbow. “I usually am.”