If all goes well, this should be the last time Castiel has to sneak into this godforsaken office building. It was never truly a nice place, but it's really gone to shit over the last decade and a half. This is where most of the Hunters were staying when Castiel first joined the gang, and every time he comes back, he's struck by some bittersweet memories.

With the three envelopes in one hand and a roll of duct tape in the other, he climbs the stairs in the darkness. At least there's still a little sun coming in through the windows. It doesn't do a damn thing to illuminate the staircase, but at least the rooms themselves have some light.

He's almost finished climbing the second staircase when he hears a noise on the third floor and he freezes. He wasn't expecting anyone to be here. The Hunters had stopped using this place on the regular before Castiel had even left, though for the most part, other gangs stayed away from it just in case. He'd assumed it was still considered Hunter territory if this is where Dean had decided to meet, but if that had been the case, he would have expected it to stay empty.

He pauses for a few seconds, weighing his options. He could tape the letters to the wall on the second floor and just hope that if Dean comes by again, he sees them there. He could leave and come back later when the third floor will hopefully be empty. Or he could head to the third floor anyway just to see what's going on.

The last option had been more of a sarcastic take on the situation, but when he realizes the sounds he hears from above appear to be sobs, he actually starts to take that one seriously. He has absolutely no idea what to expect and he knows he won't be a welcome surprise, but maybe if whoever up there is a Hunter, they can tell Dean about these letters when they get the chance. And if it's not a Hunter, as long as they're not in another gang, he can probably just leave the letters here anyway.

Castiel puts the roll of duct tape and the three envelopes in his left hand so he can hold his gun in his right. He keeps it down by his side and he climbs the rest of the stairs. He doesn't want to come off as a threat, but he doesn't want to walk into this unarmed, either. He finishes climbing the stairs and...

"Jack?" Castiel slips his gun back into his holster. He's pretty confident he won't be needing it.

Jack's head snaps up to reveal his tear-stained face. "Castiel?" He immediately wipes his eyes, as if that will do anything to hide the fact that he's been crying. "What are you doing here?"

"Oh, I..." He holds up the envelopes for a few seconds. That's really the last thing on his mind right now, so he puts them back down by his side. "What's wrong?"

Jack sniffles. "Nothing. I'm --" He forces a very obviously fake smile. "I'm fine."

CastieI frowns. He's very much not fine, but Castiel has a lot of experience pretending to be, too, and he doesn't want to push. He doesn't want to do nothing, though, either. After a brief moment of deliberation, he decides the best response is probably just, "Well, if you decide you're not fine — or even if you are — and you want to talk, I'd be more than willing to lend an ear."

Jack hesitates. "Dean told me to be careful what I say to you."

CastieI waves that off. "Don't let Dean's paranoia fool you. If I wanted you in jail, you'd be there already."

"Oh." Jack thinks about that for a moment. "I guess you have a point."

CastieI gives him a small smile. "So if you want to talk, I've got nowhere to be. If you just want me to leave, that's fine, too."

Jack takes a minute to think it over. Finally, he asks, "Do you promise you won't tell anyone?"

"I promise," Castiel replies.

"Especially Dean," Jack adds quickly.

CastieI cocks his head to the side. He wasn't exactly expecting a response of "Pinky promise?" like he would have given as a toddler, but this is arguably just as surprising. The Hunters are — or were, at least, once upon a time — a family. CastieI had assumed he'd want to shield this from the cops, but from Dean, too? What could be so bad that even Dean can't know?

But he still says, "Of course," no questions asked. If he won't say it to Dean, the honorary dad of the gang, he must not have a lot of options. Castiel doesn't want to let him down.

"Okay, um..." Jack clasps his hands in his lap and drops his gaze.

CastieI sits down across from him with his legs crossed. He lays the envelopes and the roll of duct tape on the floor behind him. He wants Jack to know he has his full attention.

"I mean..." Jack sighs. "I just really, really miss Alex." With that, he breaks down crying again.

Castiel looks around uncomfortably. Had this been, say, Charlie, he would have pulled her into a hug and whispered quiet reassurances until she felt better. He's not sure that's a good idea with Jack. Castiel may feel like he knows the kid, but he has to remember that the feeling isn't mutual. He doesn't want to be that weird great-aunt-twice-removed at the family reunion that you haven't seen since you were three weeks old but she insists you're basically best friends.

Fortunately for him, Jack keeps talking, and he doesn't have to figure out what to do anymore.

"And I can't talk about it to anyone because everyone knows it's all my fault and what right do I have to complain, you know?"

"Jack," Castiel says quietly, and the boy reluctantly raises his gaze to meet his. "You don't have to mourn alone. I promise, people care. Your dad told me himself — err, wrote to me — just before I saw you last time that he was worried about you because you weren't talking about it. He would like nothing more than to help you deal with this."

Jack sniffles. "Really?"

CastieI nods. "You're a good kid, Jack, and there are so many people who love you. It doesn't matter what you think you've done or how responsible you think you are. You can always count on your family to be there for you." Castiel learned that firsthand.

"Thanks," Jack says, and the corners of his lips turn up for the briefest moment. "But this isn't a case of misplaced blame or anything. It really was my fault."

"Really?" Castiel cocks an eyebrow skeptically. "Did you pull the trigger?"

Jack shakes his head. "We were just at the mall. The fro-yo shop always has free samples and they're so much more satisfying than the actual-size cups. It was all my idea — go in through the mall employee entrance, grab a couple samples, and head out the way we came.

"But there were two Vamps outside when we left and Alex tried to stop us — she recognized them 'cause that kidnapped her a few years after you left but she made it back eventually — but Claire and I were already outside and the Vamps saw us and the Vamps saw her and I guess in hindsight it was too late to leave but I said we should go back where we'd come from and Claire said we should just shoot them and run but we spent too long arguing that —"

"Okay, Jack..." Castiel puts a hand on his shoulder. "Take a deep breath. You sound like you're about to pass out."

Jack nods and does as he's told. Castiel waits for a moment to make sure the kid is okay before he takes his hand back. He's pretty sure Jack had only taken two breaths the entire time he was explaining what happened and it's entirely possible he would have seen the boy's face turning blue if there had been any more light in the room.

Now that there's oxygen in his lungs, Jack continues, "The Vamps came over and they were, like, harassing us, which was fine, I guess. Annoying, but fine. But they kept saying they were gonna bring Alex back, and she kept saying no, that she was happy with us, and things escalated really fast and they —" He squeezes his eyes shut and swallows hard. "They shot her. In the chest. Said they'd rather lose her to the devil than the Hunters. And I just keep thinking, if I hadn't wanted that fro-yo so much, if I hadn't fought with Claire about what to do, Alex would still be here."

Castiel is fully aware that this is only one side of the story and that it may just be a classic case of an unreliable narrator, but from what Jack says, it really does sound like the Vamps started it. And, though he doesn't say it, it also sounds like he and Claire finished it — there were two other dead bodies on the scene, and Castiel hopes to god it was the Vamps. After what they did to Alex, they deserved it.

Unless there's something Jack isn't telling him — and he has a hard time believing that; this sounded like a full confession to him — it really doesn't sound like Jack's fault. He's not sure he expects to be able to convince him of that, but it's worth a try.

"But did you pull the trigger on her?" Castiel asks, a repeat of her earlier question.

"Well, no, but I —"

"Did you hand the Vamp a gun and ask him to shoot her?" Castiel continues.

"No, but —"

"Did you grab her by the waist and hold her out in front of you like a human shield?"

The corners of Jack's mouth twitch up just a little at that. "No."

"Did you throw her at them like a baseball to distract them so you could take off running?" CastieI asks.

That one earns a real smile, and though he's clearly still upset, he seems to find that concept at least a little amusing.

"Then it wasn't your fault," Castiel says. "You just wanted some fro-yo. You had no idea anything else was going to happen and there was nothing you could have done. Don't be too hard on yourself. It's hard enough to mourn a friend without feeling guilty about it."

Jack wipes the tears from his eyes. "I wish you'd never left. You're like a fountain of wisdom."

Castiel chuckles. "Well, that's what I'm here for now." He knows what Jack is feeling, at least in regards to wishing he had someone to talk to. CastieI was in the same boat when he was 16, and though he knew that he could always talk to his brothers, sometimes he just knew it wouldn't help. There was always one person he could always count on to make him feel better, though. "Any wisdom I have, Dean probably has too. You can always talk to him, too." They're a lot more alike than Castiel cares to admit.

"No, I can't," Jack says.

Of course you can, Castiel wants to tell him. Everyone can always talk to Dean. He's practically the Hunters' therapist but without the soul-searching advice. But this isn't the same gang he left all those years ago. It was easy when it was just a bunch of lost kids. Leadership roles aside, everyone was equal. Castiel has no idea how things may have changed now that Dean is old enough to be some of these kids' dad. Maybe Jack has a valid reason not to want to talk to him.

So instead, Castiel asks, "Why can't you talk to him?"

"Because," Jack says, "he told me a few days ago that he was proud of me for dealing so well. I can't just tell him that he's wrong."

"Why not?" CastieI asks, and it really is a genuine question. He doesn't think Jack is wrong or dramatic. He's genuinely curious.

"Because..." Jack sighs. "I just don't want him to be disappointed in me."

Ah, that would make sense. Castiel's response is simple, and he hopes his tone conveys his sincerity when he says, "He won't be."

"You don't know that."

A small smile grows on his lips. He feels bad — it must look like a strange reaction to Jack — but he can't help it. Jack has absolutely no idea how wrong he is.

"Hey Jack," he says, "if I tell you a story, do you promise not to tell Dean that I told you?" It seems only fair, given that Castiel made the same promise for him. The difference is that Jack is afraid that Dean would be disappointed if word got out; CastieI is half-convinced he'd end up with a bullet through the head.

"I guess," Jack says warily.

"I've known Dean since we were younger than you are now," Castiel begins. "I didn't see the beginning of the Hunters, but I did see a lot of the firsts. I actually remember the first time a Hunter died.

"I think we were about your age, Dean and I, and we were just sitting around drinking beers or whatever because it was the middle of the night and none of us wanted to go to sleep. And one of the other Hunters came running into the room in tears, and all she could say was, 'Anael's dead.' Apparently the two of them had gone out to bribe their way into a pack of cigarettes and they got jumped on the way back. Only one of them got away; Anael..." He trails off. He'd rather not think about what happened to her.

"Dean barely knew her," Castiel says. "She'd only been there for a couple months and she spent most of her time with her friends, not with us. And do you know what Dean did when he heard that this girl he barely knew died?"

"What?" Jack asks.

"He cried like a little bitch."

Admittedly, this is a poor summary of how Dean responded, but in the technical sense, it's not untrue. His bluntness earns a small smile from Jack, and that alone is enough to assure Castiel that he's done a good job with this story. Now he just has to make his point.

"Dean didn't say he's proud of you because he thinks that's how you should be acting and how you should be coping," Castiel says. "He said it because he's surprised that you are because he knows damn well that he wouldn't be doing as well as you're pretending you are. There's no shame in admitting that you're mourning. He'll understand."

Jack sniffles. "Are you sure you're not making this up to make me feel better? Because that doesn't sound like Dean."

"Well, he's seen a lot of shit since then," Castiel says. "He's had time to adapt. But he knows firsthand how hard it is to lose someone, and he knows what it's like to feel like you could have done something about it. You don't have to worry about disappointing him, I promise."

Jack gives him a small smile. "Thank you. I think I really needed to hear that."

"You're welcome," Castiel says.

"I don't know how I managed before you came back," Jack adds. "You really know just what to say."

Castiel frowns. "I'm not really 'back,' you know."

"Well, yeah," Jack says, "you're still a cop or whatever, but you're around now. That's enough for me."

CastieI sighs. He didn't realize Jack thought this was anything more than a brief back-and-forth with Dean before he went back to his ordinary life like nothing ever happened. He feels bad, getting the kid's hopes up like this. He should probably clear things up instead of just disappearing with no warning like he did the first time.

"I'm not going to be around after today," Castiel tells him. "I actually wasn't planning on 'being around' today. I was just going to leave something here for Dean and that was going to be it."

"Oh." Jack frowns. "Well, that's okay, I guess. I'm glad I at least got to see you again."

"I am, too," Castiel says. "Seeing you all grown up has been the highlight of these last few weeks. If I thought I could keep in touch without putting the rest of my life in jeopardy, I promise, I would." He pats him on the leg. "You're a good kid. I'm really gonna miss you."

"I'm gonna miss you, too," Jack says.

Castiel reaches back for the letters he brought with him. It really feels like they've reached their final goodbye, and he doesn't want to drag it out any longer than he has to. He finds himself hesitating, though. Jack means a lot to him, and it seems the feeling is mutual. As much as Castiel wants to stay out of this gang stuff, he can't bring himself to leave Jack in the dust like this. Even with Lucifer, Gabriel, and Dean around, it still feels like he's just leaving the kid all on his own. He can't do that.

"Do you want my phone number or my address or something in case you need to reach me?" he asks. "Not, like, every day, but if there's an emergency or you have another day like today or...?"

Jack hesitates. "I don't know. Dean might get mad. I mean, he likes you, but he doesn't really want me talking to you like this. You know, 'cause you're a cop."

"That's fair," Castiel says. He'd assumed as much. Dean doesn't seem to think he's very trustworthy, and he can't say he blames the guy. "If you don't want to risk Dean getting mad, that's totally fine, but if you think you can keep it a secret, I'll give it to you anyway. It's up to you."

Jack thinks that over for a few moments. Finally, he says, "Can you write it in the notes app on my phone? No one's gonna go through all my phone notes."

"Sure," Castiel says. Whatever works for him.

Jack takes out his phone and, after tapping a few times, hands it to him. He's in the middle of an existing note, which Castiel supposes makes sense. That's an easy way to hide it. Castiel types his phone number and his address with no other context, then hands the phone back.

"And Jack," Castiel says, "if you ever decide that you don't want to be a Hunter, come find me. I can help you get out. Just don't tell anyone or Dean might kill me." He says that last part with a small smile just so Jack doesn't actually think it might be a death sentence. Maybe if someone else was trying to help the Hunters out of the gang he might resort to violence, but he wouldn't hurt Castiel over something like that. Probably.

"I don't think I will," Jack says, "but I'll remember that just in case. Thank you."

"Any time," Castiel says. "I should probably get going, but can I ask you a favor?"

Jack just nods.

Castiel grabs the three envelopes he came here with and holds them out to him. "When you head back -- whenever that is; don't rush on my account -- can you give these to your dad, your uncle, and Dean?"

"What are they?" Jack asks, then adds a quick, "if you're comfortable telling me."

Castiel hadn't been planning on telling him, but he asked so politely that he feels like he has to give him some sort of answer. "The ones for your dad and uncle are just responses to the ones they wrote for me. The one for Dean is..." How does he phrase this? "It's a heads-up." A warning, more accurately, though that sounds more ominous than he'd been going for.

"Oh." Jack pauses. "Do you want to tell him in person? I know where he is."

"I don't think Dean wants me any closer to Hunter territory than I am right now," Castiel says. If he was welcome, Dean would have invited him. As it stands now, he thinks he'd have to rejoin the Hunters for an invitation.

"I don't think he'd care," Jack says. "As long as you don't turn us in, it's all good, right?"

"I don't know if Dean will see it that way," Castiel says.

"You just told me not to worry him," Jack reminds him. "You should stop worrying about him, too."

Castiel scoffs. "These are two completely different situa--"

"Please?" Jack interrupts. "'Cause otherwise I'll have to go back alone and I don't want to."

Castiel hesitates, but, after much deliberation, Jack's puppy eyes seal the deal and he sighs. "Alright, I guess I can walk you back."

Jack beams. "Yay! Let's go!"