2016's Cas POV

I…am not quite sure what is happening.

Dean seemed almost nervous when the evening started—awkwardly pausing during the middle of conversations and rocking his seat back and forth on two legs until I finally put my hand on the chair to stop him. When I raised an eyebrow in question, he mumbled something and ducked my gaze.

However, once he got some drinks into him—quite a few more drinks that he'd usually indulge in on a night like this—his behavior seemed to change in the opposite direction. A woman stopped by our table and mentioned that my striped tie brought out my eyes—but Dean seemed very adamant that I looked better in the solid blue one. He smiled a little sloppily when I told him I would wear it more often.

By the time another hour had passed, he'd also mentioned that the way I throw angel blades is "really fuckin' cool" and that he misses how messed up my hair used to be; then, to demonstrate the point, he ruffles his fingers through it. The touch is…surprisingly nice and I try not to lean into it.

I know I should stop him. If he remembers all this in the morning, he's going to be embarrassed and that could very easily tip over into anger when we've just reconciled. But he's rarely ever bright and free like this, not even when he's drunk, and it makes it hard to worry about tomorrow's problems.

I glance at the younger Dean. He seems uncomfortable. That, more than anything, has me questioning what I'm doing.

However, just as I open my mouth to offer to heal the older Dean sober, he announces he is going to the bathroom. "Yeah, me too," the past version says, scrambling out of his seat.

Sam flashes them a look of concern as they go, so apparently, I am not the only one who has noticed something off.

"Do you think that Dean is OK?" I ask him over the clink of glasses and the cheers and groans of people winning and losing at pool.

Sam's fingers twitch briefly around his beer bottle. "Seems fine to me," he says, casually, before taking a swig. He doesn't look at me when he says it.

Suspicion rises in me, like oil floating to the surface of water. Of course, there's a reason Dean is acting like this—and not because he suddenly wants to.

Abruptly, I stand, knocking my chair back a little harder than I intended. I don't have the excuses humans do for leaving a situation they find awkward—no need to use the bathroom or get a breath of fresh air. I can't even claim tiredness—so I just say, "I'm going outside" and then do.

I'm guessing Sam watches me leave the same way that he watched the Deans—but I dismiss the thought as irrelevant.

For now, it's just me, a couple of smokers, and the orange-yellow halo cast by the neon signs.

As an angel, there was a time in my eternal existence when I would automatically turn my head towards the heavens when I felt in need of answers. Instead, I find myself distracted by a pair of fuzzy dice that are hanging from the mirror of a nearby pickup truck. If Dean is any indication, a person's car is often an extension of their personality and I wonder what the owner of these dice thinks of when he or she catches sight of them swinging.

15 minutes pass before he comes after me—and it is almost with regret that I let the twisted, half-formed feeling that drove me outside loosen. Forgiveness is a virtue. And yet, sometimes, I question the speed with which I forgive Dean Winchester just because he looks regretful.

"Heya, Cas," he murmurs, one hand in his pocket.

"Hello, Dean."

The neon buzzes.

"Sorry about tonight," Dean admits at last, with a half-smile that reminds me of the half-moon overhead.

"What part do you feel sorry for?" I ask, genuinely curious.

He blinks at me, surprised.

Then, he takes another minute to think it over. "Would it be bad if I said I don't know? It sorta depends on how this next part plays out."

It's an honest answer—and one I am in a unique position to sympathize with. After all, I once apologized to Dean for keeping my secret alliance from Crowley hidden from him; it was only after the Leviathans poisoned me from the inside out that I was sorry to have made the alliance in the first place. "Tell me when you know then."

A silence stretches between us, but rather than becoming more tense, we relax into it. Dean comes to stand more firmly beside me with our backs to the bar's brick wall. He smells like leather and the color teal and vaguely like the beeswax lotion I gave him that he only sometimes admits to using.

"I talked to Mini Me," Dean says, a few moments after the smokers have crushed their dead buds into the ground with their boots and departed. I nod to let him know that I'm listening. "It's weird to be on this end of things. Like, I keep telling him 'this is your future' without realizing I sound like all those other douchebags who've told me to shut up and play my role."

It's an idea I hadn't considered either. "I…suppose by one interpretation, we are doing the work of God here. Making sure the Apocalypse stays on course—just our version of the Apocalypse, not the Bible's."

"Exactly! And, I cussed God out back in 2008—and for most of the years after. I couldn't understand why he allowed all that stuff to happen—the earthquakes and the plagues. Why Sam of all people had to jump into the Pit or lose his soul. I yelled at Him every single time you exploded on me. And even when he brought me or Sam or you back, I was still angry because he knew what was coming and let us die in the first place."

"And that Dean in there…" he continues, jerking his thumb backward. "He's gonna have all the same questions that I did. And just like me, he's the kind to say 'screw destiny' every chance he gets. We keep debating whether we should let him and Bobby change the past-"

"But when does anyone let a Winchester do anything?" I finish the thought for him.

I will admit that the plan—to give past Dean information about the future, hope he shares it with his Castiel, pray his Castiel accepts his role as a fallen angel and wipes Dean's memory while also staying true to the course laid out for him—has only become more complicated and grasping with time. But that's not all that's going on here.

"You want him to do it differently," I announce into the still night air.

Dean scrubs the back of his head, where his short hair meets the nape of his neck. "Yeah," he breathes.

"What changed your mind?"

He turns towards me and our shoulders inadvertently brush in the process. "I've done a lot of things I regret, Cas…but…more than that…" He closes his eyes. "God, this is gonna sound like a fuckin' cliché, but there's a lot of stuff I haven't gotten to do—experiences…with people—I've never gotten to have. He might."

I have to consciously remind my grace to pump my borrowed heart. Dean wants…what? …A family? Of course, there must be a part of him that longs for more than what Sam and I could give him—and he deserves it, too. But the thought of undoing

"Whatever missed opportunities you think you've had…" I begin quietly. "What stops you from pursuing them now?"

He opens his eyes and—I'm taken aback. I don't think I've ever seen him look like this. His walls are down. If an angel wanted to possess him right now, they might not even need a verbal 'yes' to do so and it's clear—to some extent—that that is what he is doing—inviting me in, inviting me to see. But see what?

"I don't know if I can, Cas," he whispers. "Maybe I'm too old, maybe I've lost too much, or gotten too used to playing it safe-"

"You never play it safe."

"I do," he insists, lifting his hand up almost as if he were going to smooth his fingers through my hair again. I exhale sharply and he abruptly stops. Curls his fingers in towards his palm. Drops his arm back down to his sides. "With some things, I do."

"Come on," he motions to me, pushing off the wall and gesturing back into the bar. "Before they send a search party after us."

I follow him automatically, my mind sifting through the conversation we just had for whatever meaning I've overlooked.

"Cas?" he says, as he holds the door open for me.

"Yes, Dean?"

"The blue tie really does look good on you, man. Sorry I never told you before."