To celebrate Labor Day, I've written an imagine featuring a bunch of different cast members. I hope you enjoy!

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"Hey Bobby?" You tapped the older hunter on the shoulder. He turned from talking to Ellen and smiled.
"What do you need kiddo?" It was what Bobby called you since you were ten years old. That was sixteen years ago.
"Where did you put the rest of the red plastic cups?" Ash had taken the last one just as you were about to pour yourself a beer. 
"They're in the cabinet above the fridge. Got it?" You nodded.
"Thanks Bobby." He went back to his conversation with Ellen. They were talking about some hunt they had done together a few years ago. You walked into the house and weaved your way through the rooms until you got to the kitchen. 

Bobby, Sam, Dean, and yourself had decided to have a barbecue at Bobby's to celebrate Labor Day this year. As hunters, you worked harder than most and deserved at least one day off. You'd invited everyone from the roadhouse as well as a few angels, including Cas, Gabriel, and Balthazar. There was also a few hunters that you didn't know too well but who were great friends with Bobby. It was nice to meet all of the new people. 

Dean and Cas were sitting at the kitchen table talking about everything except hunting. When I walked in, they looked up from their conversation and waved. "Hello (Y/N)." Cas greeted. "Would you like to join in on our conversation?" 
"I would, but I have to get these outside and grab myself a beer." You told him. 
"Here. You can have mine. And Cas'll take care of the cups." Sure enough, Cas took the cups, disappeared for two seconds, then reappeared. "Problem solved."
"Thanks guys. So, what are we talking about?" You asked them. 
"We were just talking about how much we appreciate having a day off. It's not very often that we don't have to worry about monsters, demons, and dick angels. Might as well make the most of it." Cas gave Dean a look when he described angels as dicks, but then went back to his normal self.
"You should go find my brothers. They're probably outside. They wanted to hang out with you earlier, but you were talking to Jo."
"Alright. See ya later!"

Sure enough, you found Gabriel and Balthazar with Sam, Jo, Rufus, and Garth. "Hey guys! Enjoying yourselves?" You greeted the group. Gabriel popped the lollipop out of his mouth and held it up.
"Yup!" He said. Balthazar took the candy out of his brother's hand. 
"You sure know how to throw a party." You never got tired of his accent. 
"Yeah, well, Dean and Bobby helped." 
"Don't forget about me!" Sam yelled from the opposite side of the circle. 
"Oh, and Sam, too."

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Later that night, you all sat in lawn chairs scattered around a bonfire. You watched the reflection of the flames in everyone's eyes as they talked among themselves. Nothing could ruin your good mood tonight. This was your family, and it felt like the greatest thing in the world to see them all so care-free, even if it was just for one night.