Do you think Chuck ever sits up there and is just like, “Freaking really, guys?” And then he sighs and takes a sip of his whiskey and shouts down from the fluffy clouds above:
“Was the ‘raising him from perdition, leaving your grace imprinted on his freaking skin’ not a clear enough sign that maybe, just maybe, I think this is the one for you?
No? When you rebelled against Heaven and you did it all for him and I didn’t immediately smite your feathery butt, that not a sign?
How about all the times you died, Cas? OR, OR you know, killed yourself, and I brought you back! Back to him! He’s the first person you come to and the first person you see as you regain sense of your angel-ness, and THAT’S not a clue, REALLY?
And Dean! Dean! You’re charging through Purgatory, screaming for your angel, and you find him on the banks of ‘the river’, cleansing himself, purifying himself in my waters, you find him like that and it never occurs to you that I’m doing my best to get you guys together?
Not even as you see him in your dreams, in the night, on the road, in the bathroom? Really?”
And then, because he can’t freaking take it anymore, Chuck starts going for the real obvious…
“Oh dear me! The Impala’s got a flat tire! And it’s just the two of you, cause Sam ‘lost’ his computer charger back at the motel! And, oh boy, it seems to be getting hotter out here doesn’t it? Oh look, Cas! It’s so hot that Dean has to take his shirt off, because changing a tire is hard, hard work, and it makes him sweaty…”
“Oh, oh no, there’s seems to be a HUGE thunderstorm on the horizon! Thank goodness you two found that deserted log cabin…Oh, opps! No power! Guess you’ll have to start a roaring fire… Hey… lookie there, whiskey! And two glasses! And, man, that bear skin rug you didn’t notice before is startin’ to look real inviting, isn’t it?”
And then, Dean and Cas just sit awkwardly on the couch together, close, but not close enough to touch, stealing glances at one another in the fire light, but not moving…
And Chuck is just like, “Ugh. Fine. Don’t fall in love, get laid, get married, be happy together forever ‘cause you’re totally soul mates. I DON’T CARE! I DON’T CARE AT ALL! … I’m going to find a puppy for Sam.”