Things were slowly, slowly stabilizing. Chuck had been gone about three months by now, and they were beginning to unclench. Cas had been returned from The Empty, Jack had figured out a way to make the world self-sufficient enough that for the most part, he could be with his family as well, and the Winchesters, well, the Winchesters were still sorting out their own post-Chuck lives, what they honestly wanted their futures to look like. At least now they had all the time to figure that sort of thing out.

When Jack comes to them, sheepish and maybe a little uncertain, holding out a flier to a local theater, they all exhale. "Yeah, sure, kid," Dean finally settles on, backing up the encouragement Cas and Sam had already given him. "What do you need from us?"

Rides to and fro, and a lot of support, ended up being the gist of it. Jack knew how to drive on old, abandoned country roads, but actual driving in town with other people on the road with him was a little beyond him, so whoever was available would drop him off, sometimes they'd stay, sometimes they'd do some stocking up in town for whatever the bunker might be running low on at the time. Jack was thrilled, either way.

Then one day he came with another flier. Try outs, this one read. "They suggested I give it a go," he says with a hopeful grin, eyes flickering between the three of them. "Even though I'm untrained, they're impressed by how hard I work backstage and just wanna give me a chance."

Dean, Sam and Cas exchange glances before turning back to him. "That's fantastic, Jack," Sam offers. "Anything you need, just let us know. A scene partner, or- or anything!"

Dean bites his tongue at the sarcastic comment welling up there and clears his throat. "Yeah, man, just... whatever. We're here for you."

Cas smiles at his son. "I'm proud of you, Jack."

Jack grins at them, relieved and happy to have their support and blessing after everything he's done that used to make spending time with humans a non-starter. Now with his powers under control, and everything running smoothly, he trusts himself more, and so does his family. It's an incredible feeling.

-x

The try out comes and goes and the next time they see Jack, he's nervous and uncertain, biting his nails, pacing around the main halls of the bunker. "It's gonna be ok, kid," Dean tells him from where he's cleaning out the guns. "If it doesn't work out here, there'll be other tryouts. Maybe get you some formal acting classes, if you want. That might help, right?"

His eyes light up. "Can we do that? Really?"

Dean chuckles softly. "Sure, kid, why not? You did save the world in the grandest scale possible, might as well get something out of it."

Jack shakes his head. "I've gotten plenty out of it already," he says softly, and Dean's movements still as he gapes at the kid's bright smile.

"Oh," he mumbles. "I mean, yeah me too, but... You know what I meant."

Jack chuckles. "I do, Dean. Yes." Instead of pacing some more, he opts to sit and watch Dean, always in awe of how fluid and concise his movements are when it comes to this particular habit.

-x

A couple days later, the theater calls. "I... I have a small role," Jack says in awe, staring at his phone. "It only has a couple of lines, but I'll be in the background for most of the play." His eyes gleam. "I'm in a play!"

There's a snag, though, when Jack's informed everyone in the play only gets two comped tickets. "But... I have four people I want to invite..." he says quietly, Sam having to quickly interject.

"Give the comped seats to Cas and Dean, Eileen and I will be happy to pay our own way," he tells Jack with a smile. "It can be a real actual date for us. Don't worry about it, Jack. You're not excluding anyone, I promise. We understand."

Jack looks a little calmer at this and smiles. "Thank you, Sam. I hope you have fun on your date, then!"

"I'm sure we will," Eileen says cheerfully, leaning in to kiss Sam.

Dean freezes when Jack thrusts the comped tickets at him later that night, his eyes widening. "Oh, hey, kid, this is it, huh?" he finally says, finding his voice after a couple nervous swallows. "You didn't wanna give these to Sam and Eileen, or...?"

"Nope! They said they're gonna buy their own tickets, make it a date night or something. I wanted to give these to you and Castiel." He beams, not noticing the blush spreading along Dean's face.

"That... that's real nice of you, kiddo. We... uh, we're really lookin' forward to this," he says, tapping the tickets against the war room table in front of him.

"Me too!" Jack exclaims, dropping down into the chair across from Dean, already talking rapidly about his role, and the behind the scenes activity to get things done before the day of.

It's overwhelming, especially for someone who never got to do many extracurriculars in or out of school, but Dean listens intently anyway, eventually looking up to find Cas leaning against the doorway, watching them with a fond look on his face.

Dean makes a face at him and discreetly motions him in, so Cas quietly shuffles over to settle in next to Dean and the both of them listen to Jack discussing his new passion, exchanging glances before their hands find each other under the table and Dean squeezes Cas' fingers lightly, lips twitching up into a soft smile.

-x

Jack is very busy leading up to the play- there are fittings, and rehearsals, and general cast things, it results in a lot of drives back and forth. Dean sighs after another drop off for another rehearsal, dropping down next to Cas on their bed. "This kid's gonna be the death of me," he groans.

Cas chuckles and sets his book aside, hovering over Dean and pressing a lingering kiss to his shoulder. "I won't let him be," he promises, lips shifting to rest on his neck.

"Hm," Dean grunts in approval, although he makes no move to chase Cas when he moves away, too sleepy to even lift his head. "Play sounds like it's comin' along nicely at least," he mumbles.

"You stayed for rehearsal?" Cas asks softly, resting his cheek against Dean's back.

"A few minutes," he admits. "Knew the kid said not to spoil it for ourselves, but eh, ya know. Wanted to make sure everything looked on the up and up."

Cas sighs. Peppers more kisses along his spine. "I love you, Dean," he breathes into his skin.

Dean reaches out and clumsily pats Cas on the side, rubbing over his ribs lightly. "Me too, Cas," he sighs out, half-asleep. "Me too."

-x

The next day is opening night and the bunker is busier than usual as Jack gets ready, Cas and Sam trying to help him while Dean gives the Impala a tune up and Eileen does some research to pass the time. When it's finally time to leave, Jack is a bundle of nervous excitement and Dean claps him fondly on the back. "Just don't upchuck in Baby before we get there," he tells him with a smirk and Sam rolls his eyes.

"I won't!" Jack promises.

The ride into town somehow takes forever and goes by in a blink and before any of them is really ready, they're at the theater, Sam and Eileen off getting a drink and scoping out seats while Dean and Cas take a final few moments with Jack before he has to go behind the curtain to prepare with the rest of the play.

"I hope I do well," Jack murmurs, eyes bright with anxiety and hope.

"You will," Cas tells him, squeezing his arm. "I have no doubt."

"Just go back there and have a kickass time," Dean tells him. "Try to relax. You'll kill it either way, kid. Maybe afterwards, we can all go get ice cream or something."

"Thank you, I'd like that a lot," he tells them both, turning sharply when his name is called out. "Oops, that's my cue, I've gotta go!" He faces them for one more moment, Cas smiling proudly back at him. Before he can turn to dash off to answer his summons, Dean points at him.

"Hey, kid, break a leg, huh?"

Jack laughs a little and turns, rushing backstage. "Yes, hello, I'm here-"

His voice fades away into the other general cacophony and Dean sighs. "Well, Cas, guess it's time for us to find a seat, huh-"

But when he turns, Cas is staring at him with wide, angered eyes, his lips drawn into a tight, little frown, his skin looking almost sickly and grey in the faint lighting overhead.

"Cas?" he asks, thrown by this sudden change in mood. "What-"

Before he can finish speaking, Cas shakes his head angrily and pushes past him roughly into the auditorium, leaving Dean to gape after him. "'s wrong," he mumbles, confused. "What in the fuck..."

It gets worse when he goes inside. Cas has moved to sit on the other side of Eileen and Sam and Dean has no choice but to sit next to his brother, Cas diligently keeping his eyes straight ahead and ignoring him throughout the waiting period for the show to begin. Dean can barely focus on the play itself, trying to figure out what happened, or working to catch Cas' eye, something. Anything. He has no idea what's going on with the play itself, only notices when intermission starts, but that proves to be pointless as well. As soon as the lights are lifted, Cas is up and gone, Eileen and Sam casting perplexed looks at Dean.

"Ok, what did you do?" Sam finally asks, frowning at how Dean's gaze trails after Cas uncertainly, his face pale, tense.

"Honestly?" Dean mumbles, shaking his head. "I've got no damned clue, Sammy." It hurts, that Cas is so very mad at him right now, and for a reason he's not even sure of. Especially when they'd all come here to have a fun, quiet evening spent supporting Jack.

He thinks maybe, after the play, he'll have a chance to snag him, figure this out, but no, the instant it's over and the curtains have been drawn in front of the bowing line of performers, Cas is up, and gone once more. Dean stands numbly, watching him walk purposely through the crowd towards the stage door, where he knocks and clearly asks for Jack who joins him a few moments later, the two of them talking quietly before heading for the exit.

Before Dean can even find the words, Sam is speaking up. "Hey, Cas, where are you guys going? The car-"

Cas' eyes almost look like they used to, bright and glowing with rage, and Dean feels himself shrivel up and die a little, because he really thought he'd never see that kind of anger from the man again. "We are not interested in a ride, we will walk, thank you." And he guides Jack with a hand on his back to the doors, and out.

Sam gapes at Dean. "What the hell did you do?" he breathes in awe.

"I don't- nohing!" Dean cries back, throwing his arms out in frustration. "I... don't think..." His head is beginning to ache with the stress, and guilt, and a dozen other emotions he's drowning in right now. God I need a drink. "Look, just..." He tosses the Impala's keys at him. "I'm staying for awhile. Just... catch up with them and... get them home safely, huh?"

Sam catches the keys, his face softening into concern. "Dean-"

"Just go, Sammy. I'll be fine." Dean turns away from them and Sam exhales roughly behind him.

"Alright, Dean. Just... call if you need anything, alright? I'll... I'll be there."

Dean nods, clipped. They both know he won't. He stands with his hands curled into fists in his pockets until he hears Sam and Eileen leave, hoping that Cas' pride and stubbornness won't lead him into fighting Sam on driving them back to the bunker. It's a hell of a walk all the way out there in the middle of nowhere.

Once he's sure the Impala's gone, he slams out of the theater doors and breathes in the evening air before trudging down the sidewalk, his shoulders slumping as he goes. There is a promising enough looking bar down the street, with his name on it.

-x

Sam waits until they arrive back at the Bunker, Eileen giving Sam a quick kiss before disappearing into the kitchen to make snacks with Jack. He realizes they'd forgotten to take the kid out for ice cream like Dean had suggested, and sighs tiredly, turning his gaze onto Cas. "Alright, what's wrong?" he asks, still shocked by the level of tired anger exuding from the man's very pores. "Cas, c'mon, talk to me. What'd Dean do now?" He tries to sound lighthearted about it, but Cas immediately glowers at him and he backs off. "Ok, ok. Whatever he did was serious. Jeez, man, we were only gone for a couple minutes, and Jack seems ok, so what... what am I missing here?"

Cas closes his eyes and sits down with his fingers clasped together, eyes locked on his hands as he searches for the words to describe his actions, what led to them. "I truly thought after Chuck was defeated that we were turning a corner," he says quietly. "That your brother was... himself, again. That Chuck's influence had faded, and the Dean I knew the best was back. Especially when it came to Jack."

Sam nods, frowning. "Dean's really been trying with Jack, and- and with you too, lately. Unless I'm seeing things wrong?"

Cas exhales, squeezing his hands together in his lap. "Well, I must be as well, then, because I thought the same thing, until... until tonight."

Sam grimaces, sits down next to him. "Ok, man, tell me what happened tonight. Maybe I can help. Somehow."

Cas closes his eyes. "I'm unsure if anyone can, but... very well." He looks so distressed and sad when he turns to look at Sam that it's a struggle not to look away from those dark, pained eyes.

Christ, Sam thinks. Is this anything like what he looked like the night the Empty took him? No wonder Dean could barely function afterwards. He shakes his head and forces himself to focus on Cas as he tries to explain.

"Your brother..." Cas sighs, rubs his hand over his face for a moment before dropping his hand back into his lap. "Jack was about to go backstage to prepare, and Dean... Dean told him to injure himself. Just like that, apropos of nothing. I thought- I truly, honestly thought he was done wishing harm on Jack, but it was so precise what he told him to do-"

Sam freezes as Cas' words register, then lets out a strangled noise, his face twisting into such a rapidly changing wave of emotions that Cas can't pinpoint exactly what's going on with him.

"Sa- Sam?" he asks, wondering if there's some sort of spell or curse inflicting his friend right now, looking him over worriedly.

"Holy shit, Cas," Sam finally chokes out, realization dawning on him. "Was it... like, 'break a leg' or something along those lines?"

"Yes," Cas mumbles, surprised Sam guessed it right off. Does Dean say it often, that Sam could guess it so easily? How have I missed tha-

"Cas!" Sam exclaims and Cas realizes he'd probably been trying to get his attention for a few moments if the impatient twist of his lips are any indication. "Listen, it's... it's a kind of tradition, alright? What people say to performers before they hit the stage. It's silly, really, but superstition has it that telling someone good luck would probably jinx the play and its performers and cause bad things to happen, so they say 'break a leg!' instead. It's just ironic, I guess."

Cas stares at him for a long, long moment. "Are... are you joking?"

"No," Sam shakes his head. "Here." He googles it on his phone and hands it over to Cas, who frowns at the top most results before handing it back, shaking his head slowly. They sit there in tense silence, simply staring at each other for long, disbelieving moments.

"OH, oh, no," Cas gasps, suddenly scrambling to his feet. "Dean. I was so horrible to him. And he's still out there, I have to- I need to find him-" He's already rushing for the stairs, dawning horror crossing his face.

"Whoa, hey!" Sam finally calls out to him, brain catching up with the last few minutes and spurring him into motion. "Wait, wait, take these-" He passes over the Impala's keys as soon as he gets close enough to Cas, watching him close his trembling fingers around the smooth metal. "It's gonna be fine, man. He'll understand once you explain it to him."

Cas wavers at the stairs and breathes out. "I sincerely hope so," he says, quickly leaving.

Sam knuckles at his eyes and shakes his head. "God, I hope so too," he mumbles, grimacing as he walks back into the library, a wry grin crossing his face. Never a dull moment.

-x

There are only so many places Dean frequents, and the options are even slimmer in this part of town, so Cas stops outside of the bar nearest to the theater and bites his lip, staring up at it. He grimaces as he gets out of the car, wind creeping under his trenchcoat as he heads inside. It's dark and loud inside, people and music and just a general cacophony of sounds, but none of it really bothers him as soon as he catches a glimpse of familiar leather in the corner, slumped over a glass full of amber liquid.

He's still stealthy, works his way through the crowd as easy as butter, and soon finds himself sitting next to Dean, examining what of him he can see from this angle. He's not drunk, but he's so lost in his thoughts that he hasn't noticed anything going on around him. Not a good look for any hunter, and Cas feels even lower that he knows he was the root cause of the despondency on Dean's face. Finally, he breaks, leans forward and rests a hand on Dean's shoulder, squeezing. "Dean," he says into the man's ear.

Dean jerks, then squints over at him. "Cas?" he mumbles, wiping at his face with his sleeve. "What... what are you doing here?" He laughs, sounding a little manic and a lot broken. "You here to officially tell me it's over? Gonna take the kid and find somewhere else to live?" He swipes a finger over the rim of his glass and twists another gaze at Cas. "I don't blame ya, honestly. Dunno why it took this long."

"I'm not sure what you mean, Dean," Cas says softly and Dean huffs out a laugh, the sound grating and ugly in comparison to his usual bright, beautiful chortles that has always made Cas feel in ways he can't find the words for even after all of this time.

"Ah, c'mon, man," he shrugs, eyes suspiciously bright even in this poor lighting. "I told you, I'm no good in relationships. I'm too clingy, I ain't good with talking about my feelings, I have no idea what to do to make things special, or romantic, or whatever. Mix it with everything else, and it's just amazin' we made it past the first day."

Cas closes his eyes and leans in, bumping his shoulder with Dean's. "All of that is a two way street, Dean," he says quietly, is rewarded by Dean's lips twitching at his proper usage of the phrase. "And we are working on all of that, you are getting better addressing your feelings by the day, and I've never been bothered by you being ... 'clingy'..." He sighs and stares at his hands for a moment, aware by the look still lingering on Dean's face that he has only helped a little. "I never meant to make you feel this way," he says softly, wishing now that he hadn't ignored the bartender's offer to bring him a drink, needing something in-hand to work out these nerves with while he tries to explain himself. "It... Sam told me..."

"Told you what, Cas?" And god, he sounds so exhausted, pensive, as if he's just waiting for Cas to give up and go.

"The origin of 'Break a leg'." He turns, and he watches as emotions cross Dean's face, before he finally settles with a look of bitter amusement.

"Oh," he breathes out, hanging his head a little. "You thought I... You thought I was being sincere when I said that. Christ." He shakes his head, a rueful grin crossing his face. "Damn, man, I really fucked up, huh, if you thought I'd just up and say that to the kid for no good reason." He returns his focus back to the drink before him and Cas stares at him sadly.

"Not recently," Cas says quietly. "But during Chuck, there were... were moments..."

"I understand," Dean responds just as softly. "I was... I was cruel to both you and Jack a lot, especially towards the end. I guess I can't blame you for thinking it was just me falling back on old ways." He sighs, staring into the liquid, and barely sees out of the corner of his eye when Cas shakes his head roughly.

"No, that's wrong," he says. "I should've known better than to immediately jump to the worst case scenario, because this is just you, without Chuck's influence, actively working to be better. For Sam, for me, for Jack, for everyone else we know. I see the effort you've put in, that you continue to put in. I should've asked you what you meant when you said that, instead of automatically assuming... this."

Dean shrugs. "Sometimes logic ain't going to touch things like this, Cas. I get it. If someone had said or done half of the things to Sam that I did to Jack, I'd probably not even leave them breathing."

Cas sighs. "Perhaps, but I did quite a number of things that were similarly harmful to Sam and I'm still here."

"That was all in the past though," Dean protests. "It doesn't really-" He stops short, seeing the small smile Cas is giving him, and exhales. "Ah. Alright. I see what you did there."

"None of us are without blame in one way or another," Cas says quietly. "It's that we see it, and accept it, and work to be better, that makes this life we're building post-Chuck all work as well it does."

Dean hums quietly, still swirling his drink around slowly. "Guess neither of us really got to enjoy the play tonight." He sighs. "Do you know anything that happened in the damn thing?"

Cas shakes his head, and Dean laughs, then sighs, groaning into his hands. "Perhaps we... should try going to it again tomorrow night," he suggests after a moment. "If you would like. Have... have our own date night."

Dean blinks, looking over at Cas with a soft grin. "Sounds like a great idea, Cas." Feeling so much lighter since first walking in here, Dean pushes his drink away to signal he's done and slides off of the stool. "C'mon, I wanna get outta here," he says quietly, pressing his shoulder to Cas' as he tosses some money onto the bar. "You ready?"

Cas nods, settling in close to him as they walk outside. When Dean's eyes rest on the Impala, Cas holds the keys out to him, and their fingers brush against each other at the transfer.

Dean smiles at him, his free hand coming up to rest against Cas' jaw before he kisses him, slow and soft. "C'mon, maybe we can stop and get ice cream for Jack on the way."

"I'd like that," Cas agrees, hovering close to Dean, not wanting to move away, even for the few moments it'd take him to get into the car. "Dean, I-"

"No more apologizing," Dean interrupts, pressing close and kissing him again, in the deep, thorough way that he knows always flusters Cas and quiets his thoughts for at least a minute or two. He cards his fingers through Cas' hair, holding him close until easing away, both feeling the loss of it when he does. "Rain check on this until we get home. Alright?" He pulls back with a wink and Cas swallows hard.

"Of course, Dean," he agrees softly, warmth suffusing him at the word home. Only then does he find it in himself to break away to go to the car, the promise of ice cream with his family and later with Dean the encouragement he needs to keep moving.