It was a pleasant February afternoon in the town of Ponyville. It was Friday the day before Hearts and Hooves day and three little fillies were excitedly talking amongst themselves as they walked along the streets of Ponyville.
“I can’t believe Miss Cheerliee gave us the afternoon off just so she could get ready for her romantic weekend getaway with my brother,” Apple Bloom said.
“I think it’s sweet,” Sweetie Belle squeed. “Do you have any idea what our sisters are doing tomorrow?”
“Apparently they’re going on a couple’s trip with Rainbow Dash and Twilight to Las Pegasus,”
“Aww, Rainbow Dash is going out of town? I was hoping she could show me some new tricks this weekend,” Scootaloo whined.
“You can ask Rainbow Dash to teach you some new tricks anytime Scoots. Hearts and Hooves only comes once a year,” Apple Bloom said.
“I guess,” Scootaloo grumbled kicking up some dirt with her hoof.
“Hey Scootaloo,” Sweetie called.
“Yea, Sweetie?”
“I just had a thought. Is your Dad doing anything for Hearts and Hooves day?”
“My Dad?”
“Yea, he’s been living in Ponyville for almost a year now. I was just wondering if he had a special somepony or a pony he was interested in.”
Scootaloo stopped and rubbed her chin, “You know I don’t know.”
“You don’t know if your Dad is interested in anypony?” Apple Bloom asked.
“Well it’s not really something we talk about,” Scootaloo shrugged.
“Maybe he’s gay,” Sweetie blurted out.
“He could be,” Scootaloo shrugged. “It wouldn’t matter if he was. Why are you girls so interested in my Dads love life anyway?”
“How can you not be? I mean there’s always a chance that if he is seeing somepony than that pony has the potential to become your new Mom or Dad,” Apple Bloom answered.
“Well when you put it that way I guess you have a point,” Scootaloo mused.
“Hey Dad are you home?” Scootaloo called closing the door behind her. She glanced around her modernly decorated living room, and was once again relieved that the Stallion that adopted her didn’t have weird taste in decor like she originally thought he would.
“I’m in the kitchen,” a gruff sounding Stallion answered.
Scootaloo followed the voice into the kitchen. She was greeted with the sight of a dark grey unicorn stallion with a thick black mane and a glowing red horn sitting at the kitchen table going over some papers. He glanced up with his deep red eyes and smiled at Scootaloo. His fangs glistened in the afternoon light that came in through a nearby window. “You're home early today Scootaloo,” Sombra said.
“Miss Cheerliee let us out early so she could get ready for her Hearts and Hooves day trip with Big Mac.”
“I see,” he said turning his attention back to his paperwork.
“Hey Dad?”
“Hmm,” Sombra hummed.
“Do you have any plans for Hearts and Hooves Day?”
“Nope,” he simply answered.
Scootaloo stood in her kitchen trying to figure out how she should word her next question. After a few seconds she just shrugged and decided to be blunt about it, “Hey Dad is there anypony in town that you have a crush on?”
Sombra paused. He took his gaze from his paperwork and onto his adoptive daughter, “Come again?”
“Is there anypony in town that you have a crush on?” Scootaloo repeated.
Sombra just sat there mouth slightly ajar. After a minute he realized he had just been sitting there. He quickly closed his mouth and uttered, “Umm, why do you ask?”
“Well my friends and I were talking about Hearts and Hooves day and Sweetie asked if you were doing anything for it. I said I didn’t know and then they asked if you even had a special somepony and I didn’t know that either. So they asked if you had a crush on Anypony and I…”
“And you didn’t know that either,” Sombra interrupted.
“Uh huh,” Scootaloo nodded.
Sombra pushed himself against the back of his chair tipping it on its back legs and rocking back and forth for a few seconds, “To answer your question,” he began putting his chair back on all fours, “Is no I don’t have a special somepony that you don’t know about,” he chuckled. “Also no there isn’t a pony I’m currently interested in,” he added.
“Why?”
“Well I really haven’t been looking.”
“Why?”
“I’ve been too busy honestly. Running an evil organization bent on conquering Equestria isn’t easy you know and well there’s also raising you. That takes up a lot of my time as well.”
“I’m stopping you from meeting chicks?” Scootaloo asked frowning a bit.
“No no no,” Sombra said magically tousling Scootaloo’s mane to reassure her. “In fact you would probably help in me getting a marefriend. Nothing wins the heart of a mare than a single father with a cute kid,” Sombra chuckled.
“So the only reason you’re single is because you just haven’t had time to find one?”
“More or less”
“Okay, I think I understand, Scootaloo said scratching her chin and nodding slowly. “Hey Dad is it okay if I go hangout with my friends?”
“Sure, just be safe and make sure your back before dark,” Sombra replied turning his attention back to his paperwork.
“I will be,” and with that Scootaloo was off.
“So Mr. Sombra isn’t interested in any mare in town?” Sweetie asked in disbelief sitting in her usual spot in the Cutie Mark Crusader club house.
“So he is gay!” Apple Bloom exclaimed.
“I don’t think he is. He says he just hasn’t been looking. He’s been busy. Trying to take over Equestria isn’t easy you know,” Scootaloo explained.
“I reckon it isn't,” Apple Bloom nodded.
Suddenly Sweetie jumped up in excitement, “Ohh Oh Oh I just had an idea!” she exclaimed jumping up and down with a big grin on her face.
“Alright just calm down and tell us what it is. You’re beginning to shake the tree house,” Scootaloo told her.
“Well Mr. Sombra says he doesn’t have time to find a special somepony right?”
"Yea that’s what he said.”
“So why don’t we find one for him!”
“You’re not suggesting we try matchmaking again are you?”
“Yea, it didn’t work out to well the last time. Big Mac still doesn’t trust me sometimes,” Apple Bloom pouted.
“But this time we will not relay on performance enhancing drugs,” Sweetie smiled.
“Well I suppose it wouldn’t hurt to try again,” Apple Bloom relented with an eager grin.
“Why not? I’m game,” Scootaloo added with a grin as well.
Sweetie smiled and they all shouted, “CUTIE MARK CRUSADERS MATCHMAKERS YEA!!!”
Sombra sighed and relaxed into his living room couch. He had just gone over and approved the budget for the next fiscal year of the Equestrian League of Evil. His eyes hurt, his head hurt, and he was tired. A teapot went off in the kitchen. His horn light up and a few seconds later a teacup full of water and a teabag came floating towards him. He grabbed the cup and dunk the bag a few times before levitating it away in to a nearby trash can. He brought the cup to his lips and right before he took a sip a knock on his front door echoed throughout the house. He groaned and placed his tea on a nearby end table.
“Coming,” he shouted as the knocking echoed again. He opened the door and was greeted by a pale blue unicorn mare with a blue and white mane grinning at him.
“Hiya”, she said eyeing him up and down. “Wow, they were telling the truth. You are quite the looker,” she smirked letting herself in.
“Umm, who are you?”
“Me? Well my name is Minuette but you can call me Colgate,” she purred.
“Uhh, haven’t I’ve seen you around town before,” he stuttered slowly backing away from the mare and her predatory gaze.
“Perhaps,” she advanced. “I am the town’s resident dentist and I think you’re overdue for a checkup!” she pounced onto Sombra pinning him on his back. She smiled down on him as she summoned a toothbrush from thin air, “You know you have a lot of tarter build up on those fangs of yours,” she whispered into his ear in a husky voice. Suddenly she was encased in a red aura and flung out the door followed by the door slamming.
“What the hell was that,” Sombra panted out. He got up off the floor just as another set of knocking came upon his door. He tentatively approached it and grabbed the handle. He opened the door just a crack and peered through. Satisfied that it wasn’t the blue unicorn trying to get back in, he opened it all the way and regarded the plum colored earth pony on the other side, “Can I help you?”
“No I’m here to help you stud, the names Punch. Berry Punch,” she said with a lopsided smile and a wink. She stumbled through the doorway and Sombra realized that she was swaying a bit and her eyes had a semi glazed look. “Three little birdies told me you were available,” she stated attempting to swagger further into the house, but her uneven swaying was making it hard. She faltered and Sombra reached over to steady her.
“Are you al-” he recoiled from the pungent stench that wafted off her. “My Celestial women you reek!” he covered his nose and backed away.
“What you don’t like the smell of hair of the dog?”
“I don’t drink.”
Berry’s eye started to twitch, “Sorry it’s not going to work out. It’s not me it’s you,” and she bolted out of the door as fast as her legs could take her.
Sombra stood there and watched her go, until a grey blur flew in and collide with him.
“Alright I’ll get right to the point,” the pegasus mare that pinned him down began. “My name is Derpy, I’m a single mother, and I have a medical condition that makes it hard for me to focus my eyesight.”
“Uhh, nice to meet you Derpy,” Sombra said trying not to stare at the off centered eye that was clearly the cause of Derpy’s eyesight problem.
“I’m tired of the dating scene with all its little games. I need to know where this is going to go now. Dinky needs a daddy,” she said pulling a little unicorn foal off of her back.
The little unicorn filly looked down at Sombra with its little golden eyes gleaming and asked, “Are you going to be my new daddy?”
“No,” he deadpanned.
“NO!” Derpy exclaimed pulling Dinky away and placing her back on her back. “What do you mean no? Am I not good enough for you? Is the lowly clumsy Pegasus Derpy not good enough for the former king Sombra!” she spat into his face.
“Lady I don’t even know you!” he defended activating his horn and levitating Derpy off him so he could get up. “Now will you please leave my house?” he asked releasing her from his magic.
“Fine, I’ll go. You know why?”
“Cause I asked you?”
“No, it’s because I’m a strong independent mare that don’t need no stallion!” she bellowed.
“You don’t need no stallion, mommy!” Dinky echoed. As Derpy turned around and trotted out the door.
Sombra followed and closed the door behind her. He leaned against the door and sighed, “Why do I have the feeling that Scootaloo and her friends are behind all these crazy mares coming here.” Another knock resonated on the door and Sombra steeled himself before opening. On the other side was Princess Luna in all her splendor and upon her face she wore a cheap plastic Nightmare Moon mask.
“Oh Nightmare! Do come in,” Sombra said stepping to the side to let her enter.
Princess Luna gave a muffled, “Thank you,” and walked in.
“So what do I owe this pleasure?” Sombra asked closing the door. “Did I forget that we had a meeting tonight?”
“No, I was just passing through town and I thought I’d pay you a visit,” she replied.
“I see. Would you like anything to drink?”
“No no, I don’t plan on staying long. I just wanted to know if you had any plans for tomorrow.”
“Tomorrow?” Sombra asked tilting his head.
“Yes, I wanted to see if you might be interested in joining me for dinner tomorrow night,” Luna nervously blushed behind her mask.
“As in a date?”
Luna didn’t reply she only quickly nodded her increasingly blushing face.
Sombra staggered back a little and gave her an uneasy looking smile, “I’m sorry Nightmare. I…I uh… didn’t know you thought of me that way. Umm,” he scratched the back of his head and sat down. “I’m sorry. I don’t feel the same way,” he said fiddling with his hooves in an apprehensive manner. “I also think it would be bad for two colleagues such as ourselves to become even semi-romantically involved. So I’m going to have to decline. Sorry,” he finished refusing to look into the eye holes of Princess Luna’s mask.
Luna said nothing. She only stood there staring at the ground. After a few minutes she sighed and looked up at Sombra. “It’s alright,” she said with hurt clearly visible in her voice.
Sombra winced at the sound.
“I’m sorry if I made things awkward between us…I…should go. I’ll see you at work on Monday.” She weakly smiled behind her mask.
“Yea, I’ll get the door,” he said going back to the door and opening it for her.
“I hope you have a good night Sombra,” she said walking out.
“You too Nightmare,” he replied watching her walk away from the house. He stared at her flanks and sighed, “Why couldn't she be Princess Luna? Now there’s a mare I wouldn't mind going out with,” he mused. “Damn work is going to be awkward Monday,” he added. Sombra once again closed his front door, but not even before he was able to take one step away from it. Another knock thudded against it. Sombra rolled his eyes and opened the door.
On the other side stood the resident party pony Pinkie Pie, she smiled and batted her big blue eyes at him, “Hey Sombry you free this-”
He interrupted, “Pinkie this isn’t that kind of fic. Who do you think is writing this Harmony Charmer?” and with that he closed the door on her and locked it. He sighed again and turned around only to be surprised by a dark grey pegasus stallion with a silver Mohawk for a mane that was leaning against the door frame to his kitchen.
“Hey,” the stallion smiled.
“How did you get in here?” Sombra demanded.
“Through the backdoor, which incidentally is where I’m trying-”
The stallion never got a chance to finish his statement because Sombra decided to blast him (and a good portion of his roof) out of his house. Sombra watched as the Pegasus made a hectic arc through the sky before he was able to stabilize himself and fly off far away from Sombra’s house. Sombra sighed once again before going back to the couch and sitting down. He levitated his forgotten tea over and took a sip.
“Cold,” he grimaced.
Less than an hour later Scootaloo came trotting into the house. She paused after closing the door and began to wonder where the newly formed hole in the ceiling had come from. In her musing she was completely unaware of her Dad sitting on the couch sipping a steaming cup of tea.
Sombra put his cup down and cleared his throat to alert her to his presence.
Scootaloo jumped and turned to her Dad, “Oh hi Dad,” she said showing no trace of her previous startlement.
“Scootaloo did you and your friends have anything to do with those mares that visit me this afternoon?” he asked with no amusement in his voice.
Scootaloo looked away and ran a hoof through her mane, “Uhh…maybe.”
He took a deep breath and let it out, “I’m not mad Scootaloo,” he reassured her. “I just want to know why.”
“Well,” she blushed embarrassed. “You said you’ve been too busy to worry about things like finding a special somepony. So my friends and I thought we would try to help you, and try our hoof at matchmaking cutie marks,” she chuckled.
He shook his head, “Scootaloo, I appreciate the gesture but if I want to find a special somepony I’ll find her on my own. I never was one for blind dates especially when they just barge into the house uninvited.”
“Yea, when we didn't get our cutie marks we kind of figured things didn't go as planned.”
“Indeed, now where did you find those mares anyway?”
“At that singles bar outside town, you know the Desperate Pony. It’s really busy this time of year.”
“I’d imagine. The way they were acting it’s no surprise why they’re still single,” he rolled his eyes before asking, “Why did you send that stallion?”
“That was Sweetie. She thought it be good to send one in case you were gay.”
He simply nodded his head in understanding.
“Does this mean I’m not in trouble?” she sheepishly asked.
“No you are. You’re not allowed to talk about Rainbow Dash for the next two days and that hole in the roof is coming out of your allowance.”
“But Daaaaad,” Scootaloo whined.
“No buts young lady, you made things really awkward between me and Nightmare by sending her here. You know?
“Auntie Nightmare came here?” Scootaloo asked confused. “She wasn’t at the bar.”
“…Things are really going to be awkward at work on Monday now,” Sombra mumbled.
“What was that Dad?”
“Nothing, it’s time for dinner.”
In the late hours of the night Sombra sat on his couch, waiting.
A soft knock came onto his front door and he quickly got up and opened it. On the other side was a small pony, completely covered in a trench coat. The only thing visible was a camera slung around his neck.
“You got it?” Sombra asked.
The small pony simple reached into his coat and pulled out an envelope.
Sombra smiled and levitated some bits into one the pony’s coat pockets and took the envelope. “Pleasure doing business with you,” he said softly closing the door. Sombra returned to his couch and opened the parcel. He pulled out a photo. A photo of a mint colored unicorn with a minty white mane and a lyre cutie mark. He rubbed a hoof against the photo and mumbled, “One day my Minty Goddess. One day.”