Two Dearest Friends


A story where the Christmas incident never happens, and Jack and Sally find their happiness on their own. Jack Skellington, the Pumpkin King of Halloween Town, meets Sally, a ragdoll created by Dr. Finklestein. A friendship blossoms between them as he introduces her to the world outside of her tower. Sally is falling for him as their relationship grows into something more, and Jack finds the same is happening to him.

Romance / Drama
Age Rating:

A Tour

A pair of small black heels trace the side of the metallic floor. A ragdoll sits on the bed placed to the side of the room. She is tall and wears a stitched, multicolored dress made out of spare cloth. Her hair is made of red yarn and comes all the way to her lower back. Her skin consists of blue cloth that is stitched accordingly along her body. Long, black eyelashes are attached to the ends of her eyelids and adds a feminine touch to the doll.

Sally Finklestein looks down and observes the nuts and bolts mounted to the floor. Her room is fairly empty, save for a desk that contains her sewing machine and a closet to the side, filled with all of her creations. A bright line shines through the bars placed on her window and provides several rays of the pumpkin sun.

The light catches her attention. She goes to the window to watch the busy scene of the streets beneath the tower. Many monsters and creatures are walking on the sidewalks, varying from simple witches to grotesque beings. They are all citizens of Halloween Town and were to fulfill their duty of scaring the living. At least - that’s what she knew.

From afar, she can see the Skellington Manor. The mansion that towers over all of Halloween Town. It is residency to the King. One she has never set foot in, but can see the King’s observatory from her own window. Some nights she would watch the tall man pace around in that room for hours.


The ragdoll sits up in her bed. She clasps her hands in her lap and looks to the door attentively. The Doctor’s wheelchair buzzes as he makes his way up the ramps. She hears the heavy lock come off and he soon comes in.

Doctor Finklestein is her creator and the town’s mad scientist. He has a large bowl-like head with nuts and screws holding it in place. He is able to remove it off its hinge and just to scratch at his brain. It is bad habit of his, but Sally says very little about it. He always wears his usual lab coat and white pants, for he is not able to leave his wheelchair.

“I want you to be on your best behavior today, you hear me?” He asks. His voice is raspy and she flinches at the sound of it.

“Yes, Doctor.”

“And you promise not to be bothersome to Jack, correct?”

“Yes, Doctor.”

“-You know what that means, right?” His glasses shimmer. “No pestering him about questions, no speaking unless you’re spoken to, and you are to keep your manners in order. If you do not follow these rules, you will not be seeing him again. Do you understand me?”

Sally gives him another nod. He sighs and leaves the room, quickly wheeling himself out of sight. He purposefully leaves her door open but she isn’t brave enough to leave. She was afraid of being scolded for coming out to soon, or doing something wrong like she had last time.

She only gets up when she hears him calling for her. The ragdoll hangs onto the side of the rail to keep herself steady. Walking was such a trouble. She makes her way down into the main room and finds the Doctor waiting impatiently at the bottom. Beside him is a tall skeleton, who is smiling at her expectantly.

The skeleton is wearing a pinstriped suit that compliments his skinny body. A bat bow tie is placed around his neck with its wings spread out to his shoulders. A wide, stitched smile spreads across his skull. He is the king of Halloween Town, Jack Skellington.

His eye sockets meet with her black pupils for a few seconds. The skeleton leans down to whisper something to the Doctor. Wanting to know what’s he’s saying, Sally heads down the ramp at a faster rate. She nearly stumbles over and catches herself at the last second. The Doctor leans forward angrily while the tall figure eyes her with worry.

“Careful!” Finklestein exclaims. “I just sewed you together! Please, Sally, keep your footing in front of company.”

The ragdoll tenses. She corrects her posture as directed and makes her way down. She heads towards the two and gives the tall man a respectful curtsy. She lifts up the ends of her dress and bows awkwardly. She still isn’t accustomed to greeting anyone.

She says, “Your highness....”

“Please, Sally.” He motions for her to stand. “Just call me Jack.”

She looks down at the ground shamefully. “I’m sorry...”

“You better be.” The Doctor snaps. “Now let’s head into the kitchen, shall we?”

Jack lets the Doctor go ahead and faces her, giving the ragdoll a smile. He turns back around and follows into the kitchen, ushering Sally to follow behind them and keep her pace. He must notice her struggles with walking.

In the kitchen, Igor is brewing tea and has a plate of cookies. The Doctor gives his assistant a pleased look and turns around to glare at his creation. Sally distances herself from the King as he takes a seat at the head of the table. Finklestein makes no move of protest for his spot and settles at the other side.

Jack takes one of the cookies off from the plate and bites it down in one go. Sally looks and finds Igor fidgeting with his hands in the background, eagerly waiting for a response from the important man.

“Very delicious!” He compliments. “It feels like it’s been forever since I’ve had spider berry cookies...”

Igor seems satisfied and takes the kettle off from the stove. He fills the glasses around the table with tea. She quietly thanks him when he fills hers and returns it on the stove. Finklestein discreetly hands him one of his biscuits from under the table and the assistant is all too happy to chew it down. Sally, meanwhile, wraps her hand around her cup and stares at the liquid inside quietly.

“I apologize for coming so late, Doctor. I meant to make an arrangement earlier, but things just came up and all.” Jack tells him.

To Sally’s surprise, he waves it off. “It’s no trouble, my boy. I know how busy you are, and we are grateful you came as it is.”

The skeleton turns his attention to her. “I hope you can forgive me, too, Sally. The whole point of me coming was to welcome you to Halloween Town.”

She looks up from her cup of tea in surprise. Never in a million of years would she have assumed the King was here for her. She is unconsciously left to gawk at him, at a loss for words, until she hears Finklestein clear his throat at her lack of answer. A sign that she would be scolded for this later.

“-Yes, well, I’m sure she forgives you. I wanted to speak to you about next year’s project if you have the time?”

“How splendid! Unfortunately, I can’t do that today. I have an arrangement with Sally today, if you haven’t forgotten.”

She had been deflated in her chair until she hears the mention of her name, to which she perks up. An arrangement? The Doctor never mentioned such a thing. She turns to him and finds Finklestein choking on a piece of a cookie. He punches his chest and coughs loudly.

"Yes, well - ah, you see....I’m afraid I am going to have to cancel that. Sally is a very busy girl; she cooks and cleans for us. And as you can see, this place is very dusty today -”

Jack holds up a large hand to stop the Doctor mid-sentence. He falls silent at his act of authority. She watches the two with her jaw agape. She has never seen him act such a way around anyone, as HE was the one who usually had the upper hand with people. It, to say at the least.

“I’d much rather hear from Sally herself, if you don’t mind.”

She goes quiet at the sudden attention, the gaze of her creator and her King making her hunch her shoulders. She notices the scowl on Finklestein’s face and quietly ponders on what to say. She would not to say something wrong - that would surely leave her a punishment - but, then again, she shouldn’t leave Jack hanging. He was waiting for her answer-

“I’m afraid that she cannot go.”

There is a small amount of spite that leaves his voice, most likely angered by the lack of her response. Again. The two of them look over and find the Doctor fiddling with his cup’s handle. He notices the attention and clears his throat, avoiding the King’s eye sockets.

“I respect that you care for everyone in the town, but Sally here is just....not ready.”

“Not ready?” He repeats.

“I created her only 2 months ago. I want to have her study the basics of living before she can go out into town. I need about a year for her until she is able to come outside.”

Jack’s smile fades as he thinks of what to say. Sally finds herself both embarrassed and angry at the Doctor’s response. She could have prevented this by simply saying something - but at the same time, it wasn’t any of his right to decide FOR her. She could never argue with him, but Jack could. Finklestein was only a commoner compared to him, right?

“Pardon me for saying this, Doctor...But that was the most ridiculous thing I’ve heard.”

“Excuse me?”

“If you really want Sally here to understand the aspects of Halloween Town, you must bring her outside so she knows what she’s dealing with. This isn’t the human world, you know. Some of the creatures here are far too ecstatic and she needs to understand that they can scare her at any time. The books you’re making her read are far too outdated with these times.”

He looks over at her for a moment, adding: “-And from what it sounds, Sally must be clever if she’s already cooking and cleaning. Surely she must be ready to meet the other townspeople by now?”

The ragdoll is breathless, gawking at his words. The three of them sit in silence as the tension lingers about the room. Sally fidgets with her cup until she brings up the courage to speak.

“I....I think I’m ready, Doctor...If Jack thinks I can, then maybe I could-”

“You may take her.” Finklestein ignores her. “But I do NOT want my creation outside of this tower for too long.”

Jack grins at this information and stands in his chair. He nearly hits his skull at the low ceiling but ducks before he can. “-Glad I could get through to you, Doctor. I assure you that she will be in safe hands, and that she will return as soon as we are done.”

The skeleton makes his way around the table to offer a hand to her. The ragdoll looks for Finklestein’s approval and finds that his gaze is nowhere near hers. She accepts Jack’s hand as he helps her stand in an instant. The force causes her to almost lose her balance but his grip tightens to support her.

The ragdoll clutches onto him as he leads her out from the kitchen. She finds herself stumbling on the way, relying on Jack’s arm more than anything in the world, but as soon as she looks up, she is in Halloween Town.

The first step they need to take is getting down the stairs. Which is not a problem if you weren’t Sally. She’s only been up them once, and even then she had the Doctor’s wheelchair to balance on. All she has now was the King’s hand that was getting farther away from her as the seconds came by. She grabbed for it out of panic and used it to help her down. She finds him looking at her curiously, and removes her hand before he can say anything.

There is a blush forming on her cheeks. She recognized this feeling - embarrassment. She already failed to talk to Jack two times now. He must be thinking very poorly of her. And the Doctor...oh, dear. She was sure she’d get an earful from him when she came back. A voice drags her from her thoughts before she they get any deeper.

“Thank you. For coming with me.”

She turns to him and bows her head. “Th-thank you for having me.”

Her eyes slowly creep over to his figure. The way he walks is intriguing. His long legs enable him to take much farther steps than hers, yet he was able to keep with her slow pace easily. He catches her staring and she quickly looks away, pretending to be interested in the wall beside her.

“I don’t know what Finklestein has told you before, but Halloween Town is not as bad as he may make it out to be. Many of the people here are friendly and will be happy to meet you, I assure.”

She fidgets with her hands. She was so nervous and didn’t know where to begin. She spent so long staring at his house that she almost forgot he was real. His presence made her leaves tingle and her mind race. He was much more elegant and attractive than she’d have ever imagined. His voice was angelic, his smile was contagious, and something about the way he moved just...fascinated her.

“I hope it’s not rude to say, but you are awfully shy.”

She blushes at the term and looks away. “The Doctor told me not to speak unless spoken to.”

“Yes, while those are good manners, you shouldn’t be afraid of talking to me. Ask as many questions as you want and I will answer them as best as I can. Alright?”

She nods without even thinking. The Doctor told her otherwise -- that she shouldn’t be curious with businesses that weren’t hers, and it was rude to be, but Jack seems alright with it. Perhaps...maybe....she could-

“I am very sorry, by the way.” He says. He notices his abruptness and clarifies. “For what happened, when we met. I apologize you were in that situation. If I’d have known-”

“Oh, no, it’s perfectly alright,” She assures. He must be talking about her getting taken by those children and threatened by that...scary man. While the incident still shakes her, she was still grateful he rescued her when he did.

They suddenly approach a gate, which open the moment Jack steps towards it. Sally follows behind and gasps at the sight of the town’s marketplace. So many monsters are walking around and there ware dozens of shops and stands. From afar she can see the town’s famous fountain.

Some people begin to call out for Jack. She doesn’t even realize it until he starts to lead her through the crowds, acknowledging them briefly as they pass by. Once they are out of the way, the skeleton let out a sigh of relief.

“Sorry about that, Sally. It gets really crowded in the middle of the day! I really should have considered that and rescheduled...”

“Oh, no, it’s fine.” The words she means to think accidentally come out of her mouth. “I’m so glad to be away. This is the first time I’ve left the tower...”

She slaps her hand over her mouth in surprise. Jack, however, has already heard it, and is tilting his skull curiously at her.

“Is it? How peculiar. I’d...have thought the Doctor would let you out by now.” He pinches his lips together. “Why doesn’t he?” He notices her surprised expression. “If you don’t mind me asking, of course...”

“I....he....” Her voice falters and she closes her eyes. When she opens them, she finds Jack frowning at her. He decides to change the topic and rests a hand on her shoulder, gently turning the two of them so they were facing the shops again.

“You cook for Finklestein, is that correct?” She nods. “You might want to give that one shop in the middle a visit. It sells all kinds of spices and ingredients. But between you and me, you can get the same stuff very easily for no cost in the graveyard.”

They both continue. Sally doesn’t realize how close an eye Jack is keeping on her. Her body seems very feeble; it would be very easy to have her swept away in the crowd. And even he knows that it would take her awhile to recover from a fall. Without a word, he takes her arm and politely leads her through, glancing every so often just to make sure she is still with him.

It doesn’t take long before she succumbs to the monsters pushing against her. When he feels her start to fall, he takes a grip of her hand, but finds that it comes off completely. Against his instincts, he jumps, and lets the arm fall to the ground. A child kicks it, which sends it into the crowd. He finds Sally on the ground right behind him, and leans down to help her back up.

“Oh, dear...” Jack exclaims. “Are you okay? I’m very, very sorry-”

“Help me look for it! Please?”

She goes on her knees to desperately search about the floor. He notices the leaves escaping the hole in her arm. He ducks down and starts to gather the ones that had fallen, all before he spots a patch of blue. He picks it up and finds the hand waving at him in return.

Numbly, he turns back to her. “I’ve got your arm...”

“Oh! Thank you!”

She takes it from him and sits on a nearby bench. He watches as she takes some thread from her dress pocket and a needle from behind her ear. Then, she stitches her arm back on, knots the end of the thread, and returns the items back in their proper place.

When she looks up, she finds him eying her rather curiously. His hand was on top of his mouth, looking as if he was contemplating something. She looks away from him, feeling her hair cover her face. That may be as well - she was incredibly embarrassed...she lost her arm in front of her King!

“I...I’m sorry...” She apologizes.

“No need to be sorry.” He shakes his skull. “It’s just...”

He takes a seat next to her and observes her arm. She blushes as his fingers trail over her stitches and rubs her cheek shyly. Was he really...touching her? This was the first time anyone besides the Doctor has laid a finger on her. His hand is so warm, and incredibly bigger than hers. She watches as he slowly lets go, his look full of wonder and interest.

“That’s an amazing talent you have”

“Talent?” She repeats. “You...think it’s a talent?”

“Of course! You can do all sorts of things with dismembered limbs.” His smile grows, and she finds some sort of childish excitement in his eye sockets. He calms himself down before she can see more. “Never mind. We should be-”


A loud voice suddenly pierces everyone’s ears. The skeleton and ragdoll turn around. They find someone running towards them, their face obscured by the overwhelming amount of things that they are holding. Jack helps Sally from her seat and leads her towards the figure. He motions down the papers and reveals the Mayor’s stressed face from behind them.

“Jack, there you are!” He exclaims. “I’ve been looking for you ALL MORNING! We were supposed to go over the plans for the Pumpkin Pa-”

The Mayor stops when his eyes land on Sally. She brushes her hair behind her shoulder shyly. She’s only seen this man once before - she couldn’t quite remember his name. Though, the big badge on his chest helps her remember. He takes a step forward and bows politely.

“Hello there, Sally Finklestein!” He tips his hat. “I haven’t seen you in awhile.”

“Yes...I have not seen you, either.” She replies awkwardly. Jack notices the tension and coughs to get Mayor’s attention again.

“We were just about to head to the Graveyard. If you don’t mind, Mayor, I could really-”

“Jack, I need you to help me sort out the plans for this year! It’s urgent, and I need your signature for some very important documents!”

He places a hand on his pelvis and swipes one of the papers out from his hands impatiently. “Aren’t these the same plans as last year’s?”

“No! We’ve got suggestions on carving cats instead of bats! I could really use your help!”

The skeleton places a hand on his skull and exhales sharply. With defeat, he returns the paper and replies, “I’ll meet you in the Town Hall.”

The Mayor, satisfied with this response, runs into the direction of the Town Hall. The two of them watch as he slams the doors on his way in. Jack lets out a stressed sigh and tugs at his suit. She takes a bashful step towards him, struggling with letting the words out of her mouth. This would be the first time she’s spoken on her own.

“I...don’t mind coming with you...” She confesses.

“You really should.” Jack shakes his skull and smiles. “The Town Hall wasn’t apart of my plans. And I really don’t want to bore you.”

“It’s fine, your high-...I mean Jack. I’ll just wait until you’re done.”

She gives him a patient smile, to which he returns. He mutters an ‘alright’ and starts leading her there. When they approach the stairs, Sally freezes in her tracks. Oh, why did she agree to this? She’s going to trip and lose a leg and embarrass herself in front of Jack again...

“I see you have a problem with stairs.”

She glances up and finds him in front of her again. He’s wearing a patient smile and is offering her his arm. “-If you need help, I can gladly be of assistance.”

She bits her lip and eyes his arm worriedly. “ sure?”

“But of course. It’s my duty as a gentleman.”

She hesitates, wondering just how to take his arm. It wasn’t out of desperation like last time - he was inviting her. And she’s never had anyone do that before. She moves her hand uncertainly to it. Jack notices and slowly guides it through the space, resting her arm in his. His smile encourages her, and with his help, she climbs up the stairs with no problem.

He removes his arm from hers as they reach the top. He opens the door and politely holds it open for her. She blushes again and ducks her head as she enters inside. Within two steps, she was already mesmerized by what she saw. There is a big stage in the center of the room, shielded by a black curtain. There were many rows of empty seats in front of it and she can hear monsters moving around upstairs.

Jack places a hand on her back and ushers her to the side. She realizes how many people are in there and is thankful he moved her when he did. He leans down in front of her and gets her attention. Something beats in her chest being in such close proximity to him.

“Now, Sally, I don’t know how long I’m going to be gone, but I promise I’ll be back. In the meantime, feel free to look around and make some friends. If anyone asks, tell them you’re here with me. Is that okay?”

It really wasn’t. This was her first time outside of the tower, which would mean this would also be her first time making...what was it? Friends? Regardless, she nods. The King dismisses himself from her and disappears up the stairs. He leaves the ragdoll on her own, who eyes her surroundings wearily. She recognizes the feeling boiling in her stomach, the swelling of her chest and the uneasiness that’s crawling up her back.

She is scared.
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