Fucking Winchesters. Fuck this one Winchester in particular.

He's run across some notoriously stubborn humans before during his long tenure, that much is true. People who, for whatever reason, resisted Fate's touch. Made excuses such as "I don't deserve to be happy", "She'd never be interested in me anyway", "I don't have time for romance". Even stupider bullshit like "I'm not gay!"

And granted, there's never been an angel in the mix before. When he first got this assignment, he thought it was a joke. A prank being pulled by one of the higher-ups. One of those tasks set with the explicit purpose of serving as a test of some kind. Either to see if he could actually pull it off, or to see how soon he caught on to the joke.

Then he watched and saw how the two interacted with each other. And even without an arrow's touch, he could see that this relationship was meant to be. It could even progress naturally on its own, it they would both just get over themselves and give in.

But no. They had to make this difficult. Resist every step of the way. What should have been a milk run has turned into hours of tedious overtime. He doesn't get paid enough for this shit. In fact, he doesn't get paid at all.

Friggin' dumbasses.

He's thought about a love potion, but that isn't fair. Not just considering the ethics of the matter. For one thing, that shit doesn't last. Wears off pretty quickly. For another, if that's the route he took, the entire scenario would be wiped clean by the higher-ups. He wouldn't be surprised if they took it a step further and ret-conned their entire history together.

So that idea's out, before it even begins. He's tried the whole "put them in mortal danger until they're forced to reveal their true feelings before they die" scenario, dozens of times. It never took. Well. It sorta-but-not-really happened that one time, when the angel had been struck with the Lance of Michael, and he blurted out an "I love you" to the entire Winchester clan. That obviously doesn't count.

And Dean has yet to say the words, to anyone other than blood family.

This job is impossible.

He may just have to resort to an arrow after all. He doesn't like it; it's inelegant and more than a bit messy. More effective than a potion, though, since it pierces the heart of the matter instead of just skimming across the surface. He'd much rather let nature take its course, with a nudge here and there toward the right direction. But if he waits for that,they all just might be waiting forever.

Angels might have forever, but humans don't.

Humans don't...

That's when the lightbulb clicks on. And he notices something that has been on the edge of his awareness for a while now, and yet subconsciously blind to.

To be fair, he's never had to guide an angel toward love before. At least, that's the excuse he gives himself.

He should have been quicker, though. This is his job, after all. To think quickly on his feet, come up with solutions off the cuff. Maybe this was the test. If he pulls it off, maybe he'll get a promotion.

Unlikely, but still. Doing the right thing should be done for its own sake, after all.

Castiel's soul is beautiful. It shouldn't be possible, but it's there. A faint, slowly growing ember. He's been entwined with humans for so long and so intimately that once it took root, it wasn't questioned because it felt so right. The matchmaker never even batted an eye at its presence, because it just belonged. It took up residence like a guest and not like an invader, and then just stayed. Unnoticeable because it blended in with everyone else the angel was in contact with.

But now that it's there, and so firmly entrenched, something's gotta give. Because unless one is a Nephilim, angel grace and human soul can't co-exist. At least not in the long run.

So the matchmaker does what he can to nurture that ember and fan it into a flame. He sprinkles fairy dust on it (primitive, but effective). He contrives one-on-one situations that could be construed as romantic, hoping to feed that flame even more. (It's difficult, given there are so many people hanging around these days, but he manages). When Jack enters the picture, it provides even more grist for the mill, because if acting as a surrogate parent doesn't enhance the angel's humanity, nothing will.

Then comes the day when an actual, conscious decision needs to be made. Castiel makes it. He makes the choice that the matchmaker knew he would. Or hoped, anyway.

It's Valentine's Day, and two human men sit in a cafe, eating pie. They've just completed a hunt, and they're both oblivious to the trappings of the holiday that surround them - red and pink decorations of all kinds, banners, cards, balloons. It all goes unnoticed. It's almost midnight anyway, day almost over with.

"See? Told you you're just as useful without your angel juice. You're a hunter, same as you've always been."

Castiel squints at Dean as he scoops up another piece of pie. He puts it in his mouth and chews thoughtfully. He has the same mannerisms that he's always had, looks at Dean the same way he always has. They're still Cas and Dean.

And yet.

Castiel lowers his eyes for a second, then looks up through his lashes. "Tell me, Dean," he asks calmly, in his signature gravelly voice. "If I were to ask you out on a date, would you accept?"

Dean blinks. His mouth slowly curves up, until it forms a full-bodied grin.

"Dude. I thought you'd never ask."

Two tables away, Cupid sits with his back to them. He's nursing a coffee, black. And he smiles.