“He's a beautiful baby?”?
Sam levels Dean with a glare. "THAT'S what you're going with? We've spent all this time trying to get you two to bond, and the only thing that can come out of your mouth is 'he's a beautiful baby'?"
From his seat at the map table, Jack beams. "Thank you, Dean."
Dean shoots Jack finger guns, "You betcha, kid."
Sam runs a hand through his hair. "Jack, he's being facetious."
Jack's brows knit. "...what?"
Cas enters the room, "It means he's being sarcastic."
Dean glares at Cas, "NOW you understand that?"
Cas sits next to Jack. "You are a very handsome boy, Jack. But don't rely on Dean to tell you that." Cas puts the plate he's holding in front of Jack, gesturing to the sandwich. "Here."
Dean frowns at the sandwich. "I shoulda thought of that."
"Is this you trying to like," Sam waves a hand, "win Cas over? Or do you really feel different about Jack?"
Dean has the decency to splutter. "What?"
"You're not using bonding with Jack as a vehicle to confess to Cas, are you?"
Dean fixes Sam with an incredulous look. "How do you come to these conclusions?"
Jack takes a bite of the sandwich, talking with his mouth full, beaming. "Cas knows how you feel, Dean."
Dean flaps his lips, and Cas coughs into his hand.
"Dean," Cas starts. "I appreciate you attempting to further your relationship with Jack. But please do it for his sake, not mine."
Dean throws his hands up. "I am! Jesus!"
Jack frowns. "Jesus is not here."
Dean pinches the bridge of his nose, closing his eyes. "Everyone just--stop." He turns his attention to Jack, who is blinking owlishly at him, and oh. His head is tilted. Just like Cas's. "Jack, I don't hate you. I really am tryna be better for you, ok?"
Jack sets his sandwich down and claps his hands free of crumbs, before standing and walking over to Dean. He smiles and wraps the man up in a tight hug, Dean whuffing in surprise and awkwardly holding him in return.
"I love all of you," Jack says. "You too, Dean."
Dean swallows, looking up at the ceiling. Cas has the fondest of smiles on his lips and Sam pulls out his phone to sneak a pic--when Jack pulls away Dean offers a smile and gently knuckles his chin.
"Good, kiddo. Welcome to Team Free Will, 2.0."