AN: Hey there everybody, I'm back! Sorry I've haven't posted in a while. Kinda been crazy, but I hope to have more stories coming soon—especially since the plot bunnies started wearing ninja masks. Anyway, this is just another story intertwined into my NBC series. I got the idea after Valentine's Day. Sorry, it's kinda late, but I hope you all enjoy. Just remember to leave a review, please.

I want to say a special thanks to Werejaguar of Halloween Town, CosmicHorse, and my friend KC for helping me with character lines. Cosmic and KC really helped filling in for both Al and Kat, as well as other characters. And Werejaguar, thank you so much for editing this thing. Who knows how many mistakes I'd have if you didn't spot the "helpful" autocorrected edits.

Disclaimer: As always, I don't own Nightmare Before Christmas. That belongs to Tim Burton. I want to thank CosmicHorse for helping put the cover image (characters made on Azaleas Dolls) together with a background I found online.

Nightmares of Matchmaking

Chapter 1: An Unexpected Request

It was a quiet afternoon in Halloween Town. All around town ghouls and creatures were taking a day for themselves. The previous day had been spent in celebration of Valentine's Day. The decorations had been taken down, but there were still hints of red and black confetti caught in-between the cobblestones. Everyone in town had enjoyed the party despite the theme being a bit unusual for the Halloween citizens. However, they had managed to take their own spin on the holiday for the party.

Instead of pink and red heart cutouts hung everywhere, the townsfolk used real hearts as decorations. The Witch Shop was even selling candied hearts and all spiderwebs had been specially woven to incorporate little hearts into their designs, while the jack-o-lanterns that lined all over town were lit with red candles. There were all kinds of treats too: fried tarantulas, scorpions in red heart-shaped lollipops, chocolate covered beetles, and other wicked creepy goodies. And much like the New Year's party, everyone had dressed in midnight black or blood-red colors. It had been a fun night but now everyone had seem to decide today would be spent relaxing at home.

Up at Skellington Manor, Jack and Sally were sitting in the living room enjoying the quiet afternoon. They had decided to take advantage of the rare moment of peace and enjoy an afternoon to themselves. They had also gone to the party, but had slipped away early to enjoy a more romantic setting at home.

At the moment, Jack was reading aloud from a book, The Complete Tales and Poems of Edgar Allan Poe. Sally was nestled close to his side with her head laying against his shoulder. Her eyes were closed and a warm smile graced her face. She was not asleep but listening to Jack as he read, his melodious voice relaxing her. Zero was listening close by as well. He was curled up on his bed but unlike Sally, he was fast asleep. Jack turned the page and began to read the next line.

"There were arabesque figures with unsuited limbs and appointments. There were delirious fancies such as the madman fashions. There was much of the beautiful, much of the wanton, much of the bizarre, something of the terrible, and not a little of that which might have excited disgust. To and fro in the seven chambers there stalked, in fact, a multitude of dreams. And these — the dreams — writhed in and about, taking hue from the rooms, and causing the wild music of the orchestra to seem as the echo of their steps. And, anon, there strikes the ebony clock which stands in the hall of the velvet. And then, for a moment, all is still, and all is silent save the voice of the clock. The dreams are stiff-frozen as they stand. But the echoes of the chime die away—they have endured but an instant—and a light, half-subdued laughter floats after them as they depart. And now again the music swells, and the dreams live, and writhe to and fro more merrily than ever, taking hue from the many-tinted windows through which stream the rays from the tripods. But to the chamber which lies most westwardly of the seven, there are now none of the maskers who venture; for the night is waning away; and there flows a ruddier light through the blood-colored panes; and the blackness of the sable drapery appals; and to him whose foot falls upon the sable carpet, there comes from the near clock of ebony a muffled peal more solemnly emphatic than any which reaches their ears who indulge in the more remote gaieties of the other apartments."

Suddenly, there was a knock at the door. Jack looked up from the page wondering who it could be. He was about to get up to investigate when a soft murmur drew his attention to his fiancé. "Jack, what's going on?" Sally asked. She sat back against the couch rubbing her eyes.

"Someone's at the door," Jack replied. He leaned forward to set the book on the coffin table and stood up. "I'll only be a moment. Sorry to wake you, Sally."

"Hmm? Oh, you didn't wake me," she assured him, her eyes still closed. "I wasn't asleep. I was just caught up in listening to you read. I could listen to your voice for hours, Jack."

Jack chuckled and kissed her forehead. "I won't be long."

When he opened the door Jack was not prepared for who was standing on the other side. "Valentine?" he asked, quite surprised.

Indeed, the leader of Valentine Town stood right outside the Pumpkin King's door. He was still sporting a grey tux, pink vest, and rose-tinted glasses. However, his usual proper attire was slightly askew. His shirt and vest seemed rumpled and his chestnut hair looked as though he recently rolled out of bed. Even his beard seemed a little shaggy. Jack was confused. The few times he had met with the Holiday Leader he had known Valentine for keeping up a calm, logical appearance. As Jack looked closer, he could see the deep, dark circles under Valentine's tired eyes, making them look even darker gray, like an approaching storm cloud. Something had to be wrong.

"Is everything all right?" Jack asked, quite concerned now.

Valentine removed his glasses and rubbed his eyes with his other hand. "Terribly sorry to intrude upon you, Jack, but I am in need of your assistance," he explained. There was a gruffness to his voice when he spoke.

Jack held open the door. "Please, come inside."

"Thank you." Valentine replaced his glasses and stepped into Skellington Manor. Jack led him to the living room where Sally was waiting. She was surprised to see Valentine, but before she could ask any questions, Jack was leading the other man to one of the more comfortable chairs in the house. Seeing how exhausted he was, Sally slipped into the kitchen to make some herbal tea. While she was busy, Jack sat down on the couch across from Valentine. He noted his friend seemed more relaxed, but there was still much tension in Valentine's posture.

"Valentine, you know you are always welcome here," Jack began, "though I confess, I'm a bit worried. I hope nothing is wrong, but has something happened in your town?"

"No, no." Valentine shook his head. "I can assure you that my holiday is fine and well. The events of yesterday were one of our highest success rates by far."

It was then Sally returned with a fresh pot of pumpkin spice tea. She set the tray on the table before pouring a cup, and handing it to Valentine. "Thank you, my dear."

"My pleasure," Sally replied, filling two more cups. "Sir, if nothing is wrong with your holiday, then what seems to be troubling you?"

Valentine's demeanor then changed from tired to a more angered expression. "It's that moronic imbecile, Eros," he stated through gritted teeth.

"Eros? Whatever could be the matter with him?" Jack inquired. He took a cup of tea and waited for Sally to join him on the couch.

Valentine sighed. "Jack, you must understand that while I am in charge of caring for my holiday, that is only part of my work. Each holiday is unique in it's own way, but there are certain exceptions." He moved to place his cup on the tray before continuing. "Now, the holidays for Easter and Thanksgiving only need a few months to plan for their events. Even Sam spends his days testing new fireworks when there's been no significant political change. Then there are the other holidays. Patrick tends to people who remember what he did for Ireland, while also keeping close tabs on the people who tend to overindulge on his holiday. Afterwards, he usually spends his time to his studies. And you, my friend, must spend your days testing new ways in which to cause fear without harming anyone."

"Of course," Jack replied. "We would never intentionally hurt anyone. That was one of the reasons I had Oogie Boogie banished in the past."

"And I am glad that creature is no longer a threat," Valentine stated. "However, you are still able to take time for yourself until it becomes necessary to prepare your holiday, if I am not mistaken?"

"Well, yes…"

"Now, think of Nicholas and I," Valentine continued. "You might think our holidays run in a similar manor as the others, but there is a slight difference. You see, while the elves work year-round making toys, Nicholas must use that time monitoring the children's behavior. It is his job to ensure that children receive gifts, but while he cannot play favorites, he must also not award insubordinate behavior. Understand?"

"I think I do," Sally replied. "He wants to make the children happy, but he cannot encourage bad behavior by giving them whatever they want."

"Correct," Valentine replied. "So you see, his job requires more than simply gifting the entire world with presents."

Jack took a nervous sip with his tea. What Valentine was telling them about the other Holiday Leaders' job only brought about the guilt he felt about trying to take over Christmas. Oh, he had read in the books he had "borrowed" about the famed Naughty and Nice list, but he had not really put that part into practice during his own sleigh ride. Seeing this, Sally placed a comforting hand over Jack's. The sight of his engagement ring on her finger calmed Jack's nerves. It was a subtle reminder that Santa had forgiven him, and that it was all in the past.

Still, Jack was puzzled by what all this had to do with Valentine's current distress.

Taking another sip from his cup, Valentine went on with his story. "Now, as you know, Valentine's Day is a day for those to express their feelings to those they care about. Over the years, as with any other holiday, mine has been subjected to commercialism. That is part of the reason I employed Eros, to take the responsibility of the vulgar excuse for over glorified commercialized views on love. The boy loves the spotlight anyway," he clarified.

"But like Nicholas, I too have another aspect to my duties as leader of my holiday. You see, before all this nonsense with cards, chocolate candies and bouquets of roses, it was my duty to see to the happiness of couples. A job I take seriously to this very day. Once the excitement of my holiday ends, it is up to me to spend the rest of the year ensuring that same love and happiness remains balanced. As Nicholas monitors the behavior of children, I look at the hearts of every person around the world. I see their true selves and use that to put them on the path to finding their happy life. Now, sometimes I must be cruel but it is only to ensure that love is not taken for granted. This is where Eros and I differ. That fool would take an arsenal of those poisoned arrows of his and turn the whole world into a mess by pairing up anyone he thought would make a suitable couple."

Jack and Sally were silent for a moment. They had no idea there was so much work the other holidays had to endure.

"It sounds as though you have a lot on your plate," Jack finally stated. "I understand your concerns for your holiday, but I'm afraid I still don't understand. Has Eros done something that has upset your balance somehow? You mentioned he can be rather, uh, spirited, but…"

"Believe me, Jack, I wish he was his flamboyant self. It would be far more tolerable than this infantile state he has so graciously bestowed since last night," Valentine interrupted. "I swear, he is driving me beyond my tolerance of his infernal shenanigans. If I had remained any longer in my world with that irksome brawling scold, I would have…" He was pinching the bridge of his nose, trying to keep himself from another outburst. "Forgive me. I'm not one to be angered easily, but this time I am losing my patience with that boy."

"What has Eros done?" Sally asked, hoping she was not prying too much.

Valentine sighed. "For the last century Eros has taken it upon himself to challenge the more stubborn mortals reluctant to fall in love," he began to explain, though it pained him to talk about it. "Every year he choses one person he deems desperate for love, and focuses his energy to making their fantasies into reality."

"That doesn't sound too bad," Jack commented.

"Normally, I would agree with you, but last night the fool ran into a snare. You see, it was the first in a long time someone was able to resist his arrow."

"What do you mean?" Jack asked.

"The details of the incident are unknown to me," Valentine replied. "Eros refuses to speak of it, but apparently it does not keep him from acting like a spoil child that does not get his own way. Even his wife is unable to console him, though she has only made matters worse by coddling him."

Taking a cleansing breath, Valentine stood up from his chair to formally address the Pumpkin King. "Jack, the reason I have come here today is to ask for your help," he stated.

Jack stood, Sally following right beside him. "Valentine, I'd be honored, but what could I do to help?" he asked.

"It's not just you, Jack," Valentine added, turning to gesture to Sally. "I require the assistance of both you and your fiancé to aide me in this matter."

"Me?" Sally asked.

Valentine nodded. "My hope is to cure Eros by bringing you both to my town," he suggested. "While a constant annoyance to my work, I do require Eros' power to ensure a balance in my world. If he continues in his current state, I fear my holiday will be thrown into chaos. He won't listen to me, but I would hope he would listen to you."

"We appreciate the offer, Valentine, but how can we help?" Jack asked. It was not that he was unwilling. On the contrary, he was excited for the chance to visit Valentine Town. He still remembered his first trip to Christmas Town and recalled the experience of all the new sights and sounds. He could only imagine how wonderful a town must be that celebrated love. Though he knew it would be less macabre than what he might picture. And he would be going with Sally, his dearest friend and soon-to-be wife. It was perfect! Yet he still did not understand what he and Sally might be able to do to help out. After all, this was a bit out of their element.

"As you may recall Eros tends to have a rather abrasive personality when around young ladies, especially those on the cusp of love or around those engaged to be wed," Valentine stated, adjusting his glasses. "My hope is that by seeing you and Ms. Sally together, possibly with some discussion toward your upcoming nuptials, that he might revert back to his rather usual vivacious self. If there is one thing I know Eros loves more than playing matchmaker, it is that he adores planning a wedding."

"Is that so?" Sally cast a nervous look toward Jack and spotted the same apprehension on his face. It had been over a month since they announced their engagement, but they had not gotten much done towards planning it. Sure, they had a few helpful ideas from their friends, but there was still much they had yet to get around to.

Jack extended his sincerest apologies. "Valentine, while we appreciate you came to us for help, I fear we would not be able to do much. Sally and I haven't exactly done much planning for the wedding, I'm afraid."

"It's true," Sally added. "We haven't even picked a date."

"That's all the better," Valentine replied, starting to become a bit more enthusiastic. "With so little planning, and the amount of time you've been engaged, Eros is sure to snap out of his doldrums to assist you."

"Well…" Jack hesitated. He looked to Sally for her opinion. She looked as apprehensive as he felt. However, Valentine was in trouble and needed their help. She gave him a nod.

"Alright Valentine, we're both in."