Huntercorp Dean not meeting Cas is a crime actually
He has Negative Charm by the way, the oppostie of how Dean is full of it - so his flirting game is abysmal. He's full of cheesy cringey one-liners that literally never work on anyone, but they go so wildly over Cas's head that they get his attention anyway and end up kind of working.
Cas walks in and Huntercorp Dean is like, "HELLO. Who is this???"
Regular Dean is immediately bristling. He recognises that tone and the way he's leaning back in his seat, clearly checking Cas out. "That's Castiel, he's an Angel."
"I'll say. Every time he looks at me I feel like I'm in Heaven."
Cas voice "Actually you can't get to Heaven from here..."
"Well they must be missing an angel cause you're right here."
"Ah. None of the other angels miss me. In fact I think they're quite glad I'm gone."
Huntercorp Dean winks. "Well you can stay here with me then, cause you're definitely answering all of my prayers right now."
"You're praying to me? I can't hear you." Cas goes a little bashful. "And that's nice of you to say, Dean. You know I try to be around as much as I can."
Now full of enthusiasm because his lines are WORKING Huntercorp Dean continues flirting with Cas with 0 awareness of how bad he is at it while Cas continues to be equal parts confused and endeared.
Meanwhile Regular Dean has his head in his hands wishing a portal would open up and take the other Dean away again.
