"You seen old man North anywhere?"

The elf simply shakes its little head at him, causing the flying sprite to raise his eyebrow in curiosity. That was odd; North was always working, even on other holidays. It was how he had been able to keep up his hefty work schedule every year. For the old man not be here supervising things was very strange to the winter fae. It annoyed him.

After all, how could he mess with the strict spirit when he wasn't even around to witness it? It would be no fun, Jack Frost reasoned, to mess with his stuff if that was the case.

After flying past the elf, being sure to send a chill breeze its way to show his displeasure, Jack made his way to the old man's chambers. He was surprised to find the door unlocked; though he could have easily frozen the lock and shattered it to make his own way in. The old fae was pretty good at keeping his personal effects secure—a particular incident between the pair where Frost had messed up his lists one year—making him more wary of who he let into his room. That was one of the more controlled forms of mischief the winter sprite had visited to the Father of Christmas. He had been hoping to do so again this year, after having planned the scenario out in his head to perfection.

Yet, as he floated lazily around the room, something struck him as this not being the best time to do so. Maybe it was because the blue eyed fae had noticed the absence of North's prominently displayed scimitars over his soot covered fireplace. He usually kept them right over a particular spot; and never wore them himself unless something huge was going on. Jack knew that much from the last time the old man had had to clean up trouble; being quite content to sit on the sidelines himself and watch as he always did. It didn't really concern him what the Guardians were doing, unless of course he could find some entertainment from it. That had always been Frost's primary goal; to find as much excitement and fun in this life as possible. He knew though, that that was simply a ruse—a way for him to hide and mask the emptiness and loneliness he felt inside.

After becoming a spirit, he soon realized that most normal people couldn't perceive him; they could not see or hear him, as if he had never existed in the first place. It had been a huge shock to the fun loving farm boy, who had always been so exuberant and friendly while he was alive.

Not to say anything about his poor human family, who mourned his death while the poor fae could only watch; unable to do anything to comfort them. His poor sister had been a wreck, and the sight had nearly wrenched his heart in two. Jack had run then, flew away with tears in his ice blue eyes until he found a place that offered him the solace he needed.

That had been centuries ago, however—a long enough time that Jack had found a coping mechanism for his sorrow. Though he still could not deny the pain that was in his heart, threatening to overwhelm his small frame if he let his guard down. So he had adopted a persona of sorts; the fun loving, somewhat crass trickster who annoyed most of the older spirits that he came across. A brief smile crossed his face as he remembered a particular nasty prank he had pulled one Easter, sending a large blizzard across most of the Human World that celebrated the holiday. Much to the chagrin of one large, easily angered rabbit, who soon had caught up with him and nearly literally gave him an earful.

A small sigh escapes his cold lips then, his eyes once again focusing on the empty space with worry. If the old man had thought to take his swords with him, then this possibly was a serious situation. Or, maybe an opportunity to have some fun, Jack hoped. Either way, it certainly seemed interesting to the spirit. After looking around the room one more time, and finding nothing of interest, the fae quickly leaves, gliding through the air with a renewed curiosity. He was going to find old man North, and see what exactly he was up to. It certainly was better than waiting for the old man to return. His mind made up, the spirit left the workshop, understanding that he would find no more clues or help there as to where the Father of Christmas had scurried off to…

He could see nothing. Pitch black darkness engulfed him, dragging him under almost like quicksand of a sort, threatening to swallow him whole. Trying to command his limbs to move did nothing; they were as tightly bound as the rest of his lanky frame. Part of him was curious; where exactly was he? He understood it wasn't a good place, his emotionally exhausted brain barely able to piece together the events that had led up to this.

Part of him honestly wanted to give up, to simply lie there and let the darkness take him. After all, what could he do now? From what that thing had told him, it was planning to take over his dominion, as well as the world his formidable opponent had come from. The red clothed man had him surely beat; and the fellows he was working with didn't seem any less powerful. Was it even possible to cover the entire world in darkness? He didn't know, and a part of him was wondering if he even cared anymore. He wasn't able to help his friend, his town, or the citizens who thought so highly of him. He had failed them utterly, and that thought made his chest ache anew. What kind of a king was he, then? As if to scold him, he heard a loud voice echo in his mind, a flash of memory that had escaped him; an encounter that he had only recently remembered. He allows the thought to take him, quite content to drift off into his memories for the time being, seeing as there was nothing else he could do currently to fix his situation...

He only put a skeletal hand to his chin in thought, sockets closed in contemplation as he tried to think of anything, something to say. Movement made him turn his skull towards the sound, his sockets catching the form of a much smaller figure right next to him. They weren't paying him much attention, their profile downcast as they simply stared at their drooping feet. The sight made something in his chest ache as he saw the sadness in their eyes, tears beginning to line their pale cheeks, a frown slowly starting to make its way across his own face. Then again, after what they had been through tonight, he certainly couldn't blame them for feeling out of sorts. He wanted to say something to try and make them feel better, but honestly wasn't too sure what would work.

The ruler of Halloween Town most certainly understood what was happening with his quiet companion. Loneliness was not a foreign concept to the master of terror. Having no one to really talk to, aside from his faithful dog Zero, was a painful thing. A dog couldn't really talk back and give advice after all, no matter how well the ghost listened to Jack's mutterings. Being alone with your thoughts, day in and day out, was dangerous. He knew what it was like to have no one to confide in, no one to really listen to your problems. To need a friend to talk to...Yes, Jack understood that feeling very well.

Despite being the leader of Halloween Town, beloved by most of his citizens, The Pumpkin King didn't really count them among his friends. They admired him sure, gave him praise and adoration, but that wasn't friendship; it was flattery, empty words and something he certainly had grown tired of. They didn't make the time to know him, understand him; only seeing the facade he presented them and taking it as his real self. He wanted someone who would try and take the time to get to know him, the real him. Not that he could ever let anyone into his heart, he felt, given the status and influence he held. He didn't want to burden the townspeople with his problems, and if they saw him in such a state, their own good cheer would most definitely suffer. That wouldn't do, so the leader of All Hallows' Eve often suffered alone in his manor, not wanting anyone to see his pain.

This human had definitely made a much better start than most of the citizens in town; and the Pumpkin King could easily tell if someone was being genuine or not. They had easily proven their sincerity earlier that night, after the small 'adventure' that had ended up with the pair of them staring up at the night sky right now.

Well, that was after they had overcome their initial terror; said Master of Fright using his tricks to elicit a wail of pure distress from their tiny form after he had spotted them walking in the woods. Yet they had not run off after the initial shock, simply scanning him with downcast eyes that lacked the light he was so familiar with seeing in most human's gazes. He had been quite confused himself as to why they hadn't run off at the sight of him, dark and foreboding as he appeared this Halloween night under the canopy of trees and starlight. Most normal humans would have run off screaming; yet after their initial encounter the small thing had just simply stood there, staring up into his empty sockets with an expression he was quite familiar with. Not terror...but something worse; something he often saw in his own empty sockets whenever he gazed at his own skull, when he was alone and let his jovial persona fade. Hopelessness. Despair. Emptiness. Numbness. There were quite a few names for the emotion that he saw on their dull pupils, but he was accustomed with all of its variations.

And it was certainly the cause now of the small droplets of tears that ran down their face. Their expression hadn't changed much since, though he had noticed it brighten a few times the more they had talked throughout the night. It was usually when he spoke that they had started to listen more intently, yet Jack was somewhat wary about telling them too much about himself. That wariness lessened however, as the human quietly, shyly, asked him questions about things, and not the usual questions he was so used to getting. He honestly forgot most of his own replies, so focused on listening to someone ask him of things he'd much rather talk about than Halloween, to be honest. It was refreshing to the skeleton, and so he gave as much information as he was able.

'So...wh—what do you do when you're not out terrifying people? That can't be all you do, yeah? I mean…'

The next phrase is uttered under their breath, their head turned downwards towards the ground as their steps slowed.

'Well...Maybe I shouldn't say anything…'

He urges them to continue with a sincere smile, watching as they fidget with their hands for a few moments before speaking again.

'Ah, well—you're practically the face of Halloween, yeah? Doesn't...Doesn't it get boring doing the same thing, day in and day out? I know I'd probably get bored of it sooner or later, doing it 365 days a year.'

'Shakespeare, hmm? I've read most of his stuff, sadly I'm too dense to get it. I kinda enjoyed it though...You ever hear of a guy named Poe? I think he's got some good stuff, myself.'

'Oh! That's great!!—ah, well...I mean, it's quite something...I suppose…'

The back and forth of questions and answers continued, Jack even asking a few of his own, now honestly intrigued by this human. They answered—hesitantly, as if they were worried about boring him, their words quieter than when they had been asking him about himself. Which intrigued the skeleton; why the sudden shift in mood? He simply watched as their expression changed, eyes darting about as they tried their best to keep pace with him. It was the same attitude they had adopted before; when they had been called out by the other humans.

'Oh...well, I—I don't really...do much...I'm kinda boring, plain, y'know?'

'Why?...w-well, you just seemed—ah, never mind...It's nothing…'

He hears them mutter the next part under their breath, thanks to his great hearing from years of creeping about, listening for sounds. Their next words shock him, his sockets widening for a fraction of a second as he feels something in his rib cage start to constrict.

'...Poor guy is probably just lonely. I can get that, sure...The pain there, I can feel it as if it was my own, almost—that empty expression in his sockets...Hmmmm…'

A laugh escapes their lips then, mirthless and downcast as they put a hand to their chin in thought.

'Sorry...I just—mmmm—I don't know…'

They turn to him then, wearing a too wide smile that he knew was faked. He had used the same trick himself various times, and was pretty adept at noticing it even if the face sporting it was covered with skin.

'It's nothing...Don't mind me, heh. My head—it gets too full—too many ideas, running around...Have to let some of em out, or else I get headaches.'

'You ever get like that? Like...something inside you—I can't—I can't explain it well…'

"Well, well, well, what have we here? Jack, so kind of you to come right to me!"

He could only blink his sockets in utter surprise at that familiar baritone, the cruel tone jolting him out of his reverie. Jack knew he hadn't killed the sack of bugs; something in his ribs had told him that wasn't the last he would see of Oogie. Yet to encounter him so soon had the skeleton a bit off balance. There was little he could do but watch the sack loom over him, it's holes that were its eyes narrowing as they took in his bound form. He felt small, crawling things fall onto his skull; skittering and making his bones itch as they moved around.

"What a perfect Halloween treat that shadow gave me! You interrupted my game with the little human; it has been so long since I had a living victim! You spoiled my fun, Jack, and for that...well...it looks like you'll have to take their place!"

He didn't respond to the threat. The almighty Pumpkin King simply lay there, numb to what was happening in front of him. He barely flinched when the sack of bugs grabbed him by the front of his jacket, roughly pulling him to his feet and holding him in place. If that was the price he had to pay, for causing the death of his only friend, then so be it, he reasoned. It was only fair. Only fair that he be subjected to the same awful torture that had cost her her young life.

'Don't lay there all depressed, man! You're the Pumpkin King; Jack Skellington! If anyone can do it, you certainly can! Even if you messed up, you can still get back out there and do it again! Better than before, even. You're simply amazing, the way you can bounce back like that! I wish I could…'

As if to call him out on his melancholic thoughts, a voice echoed in his skull then, loud and piercing. It seemed to break through the depressing haze the skeleton found himself in, and he would have smiled if he still had the energy for it. Even after her death, she was still helping him more than she ever knew. He understood however, that he could do very little right now. Bound with a magic that surpassed his own, and weary from the strain of the last few hours, Jack knew that watching and waiting for the right opening was the best thing he could hope for. So he would subject himself to Oogie's games—partly to alleviate his own guilt—and break free when an opportunity presented itself. The sack of bugs had seemed to notice his change in demeanor then, his shaking appendage grabbing the lanky skeleton by his torn dress shirt as his holes for eyes set on the latter's empty sockets.

"What's so funny, pumpkin puss!? I'm going to enjoy turning you into dust!"