Castiel, Dean, Sam, and You were undercover at a 1800's themed event. They split up into pairs, Dean and Cas, Sam and you, they all go over the plan again and agree to meet back at the same spot in ten

Dean:"Okay so me and Cas will go check the front area, Sam and You will check towards the back. Sound like a plan?"

Cas:His arms are crossed, he's hand on his chin, he nods

Sam:"Sounds good to me."

Dean:"Good, let's go."

After that everyone went with their pair