Duskfall closed the door behind her and threw every warding spell she knew around the room. Not even Discord could be allowed to know what was about to go on inside that room.

Duskfall had just returned from her date with Flash Sentry and it had gone…poorly. Flash was a fine date and a nice guy, but he was painfully boring to someone with Twilight’s disposition. Any partner for her would either have to be able to somewhat keep up with her mind or offer support for her emotionally. Ideally it would be both, but Duskfall wasn’t looking for miracles.

So with stacks of parchment and many bottles of ink, Duskfall began to contemplate everyone she knew and who would maybe make a good match for Tom or Twilight.

Big Mac: Rumors he’s dating Cheerilee, but those are unconfirmed and unlikely. Applejack probably would’ve said something. Big Mac was nice and a stallion of few words, but the words he did have been surprisingly wise. Someone like that could definitely help keep Twilight grounded. Twilight found Big Mac attractive, just about every straight and bi mare did. He would also almost certainly be supportive of Twilight when duty called and she had to go halfway around the world. However, any relationship with Big Mac would certainly mean some farm work and that left the question of if the Twilight Sparkle who spent long nights reading or researching would be able to handle farm life.

The Doctor: Why the hell would I set up Twilight with that jerk? Even if he were looking for a casual romance, Twilight is likely a few centuries too young. He’s certainly capable of matching Twilight’s intellect and he’s always been shown as willing to teach, which is a big plus for an info-vore like Twilight. If I had the time to cultivate a relationship with The Doctor before setting up him and Twilight on a date maybe, but I don’t so there’s one more candidate off the list.

Blueblood: Fuck No.

Pharynx: Seems to have a thing for Rainbow. His brother Thorax likewise has a thing for Fluttershy. I don’t even know how Changelings deal with romance and the like. I think it’s best to put Changelings in general on the backburner until I have more information.

Discord: I am now really appreciating how badly skewed the male/female ratio is in Equestria. Good thing Twi is bi. Any relationship with Discord would probably involve a lot of kinky transformation stuff; a big plus for some people, but Discord doesn’t have the emotional IQ for any serious romantic relationship.

Cheerilee: Rumors of dating Big Mac unconfirmed and unlikely. My originals had little direct contact with Cheerilee, but word on the street is that she’s kind, nurturing, and strict but not harsh. She’s also a teacher, which is a big plus for both Tom and Twilight. Cheerilee won’t be winning any beauty pageants, but she isn’t homely either. She’s a solid 6 on just about anyone’s attractiveness meter, which speaks to the strength of her general appeal as opposed to one stand out feature attracting a certain crowd. I’ll have to do a little more personal observation, but I think I could easily set up Cheerilee with a date for either of my originals and they’d be perfectly happy.

The Elements: I could go over each of them individually, but they all share a common issue: Twilight would probably freak out over either Tom or herself dating one of her closest friends. This is a shame. Tom has expressed interest in Fluttershy and I’m sure if I could convince Twilight and Rainbow or Pinkie to go on a date she’d have fun at least. Applejack runs into the same problem of farm life as her brother and Rarity I fear would stretch herself too thin if she tried to juggle a serious romance with everything else in her life.

Cloud Kicker: Athletically attractive in a similar way to Rainbow Dash, Cloud Kicker has a reputation as a party animal. Between herself and her best friend Berry Punch, it’s rumored they’ve laid over 90% of Ponyville…including the Changelings. She’s a strong candidate for helping me in my own sexual experimentation.

Berry Punch: High functioning alcoholic. Instant turn off for Tom. From what I’ve observed of her Berry Punch doesn’t take anything seriously except her daughter Ruby Pinch. She doesn’t seem like the type to be tied down to a formal relationship. I’m not entirely sure how comfortable I’d be banging a mom. Neither of my originals had MILF fantasies and I didn’t grow one myself.

Derpy Hooves: The Doctor’s current ‘companion’. Utterly devoted to her daughters Dinky and Amethyst Star, known in the Hooves household by the nickname Sparkler, no one is quite sure who the father of either filly is. Digging through some old photos I discovered that Derpy and The Doctor have been around each other for years. He probably knows the identity of the father or fathers. If I really want to go conspiracy theorist, maybe they’re The Doctor’s spawn or maybe he even loomed them! Ha! Nah, that’s just too silly to be true… then again most would consider me to be too silly to be true…

Coco Pommel: A precious cinnamon roll who I inherited a strong desire to protecc from Tom and Twilight. Really, Coco is just too sweet. I could probably spend days just basking in her presence without the need to say a word. If I could fix up a date with either Tom or Twilight, I can easily see them devoting every waking moment to making Coco feel like a princess.

Moon Dancer: Moon Dancer needs support right now, not romance. That likely won’t change before it’s time for me to go.

Luna: No one is exactly sure of the nature of Luna and Chrysalis’ relationship. No one has been brave enough to ask. Luna is definitely a 10/10 in the looks department, but I wonder if she carries too much of a burden of her past for anyone not at least a couple of centuries old to be able to deal with. The same likely applies to Chrysalis, which is probably why they’re so good for each other, even if they aren’t actually dating.

Sunset Shimmer: I’d have to be really sneaky if I wanted to set up a date with her for Tom or Twilight. It’d probably be worth it though. She’s attractive, driven, and intelligent. That ticks off a lot of boxes for Tom. Twilight too, if she’d admit it to herself. I think either of them would be quite the power couple with Sunset if they took the plunge. On a completely unrelated note, that leather jacket she likes to wear is so hot.

Celestia: No. Just no. Twilight entertained a minor crush on her when she was younger, but I can’t see any attempted relationship with Celestia ending well. Too much baggage and too used to be in control for either Tom or Twilight. Strangely, I could easily see someone like Fluttershy working out a good romantic relationship with Celestia.

Twinkleshine, Lemon Hearts, and Minuette: Don’t know them well enough to make a call either way. Twilight has gotten closer to them over the past months, but they’re all still busy with their own lives.

Lyra and Bon Bon: I wonder how serious they were being with their flirting? I should ask them.

Lyra and Bonnie were just sitting down for a late lunch when there came a knock on the door. Lyra went to open the door and on the other side stood a purple Alicorn with a smile that was just slightly too big.

“Hi Lyra, hi Bonnie!” Duskfall chirped.

“Dusk, to what do we owe the pleasure?” Bonnie asked.

“Well, I was wondering how serious you were in your flirting with Tom and Twilight!” Duskfall said excitedly. Bonnie and Lyra shared a look that said a thousand words.

“We were pretty serious, but neither of them would ever take us up on it,” Lyra said dismissively.

“I know! That’s the problem! I need to know what I want out of a romantic and physical relationship so I can set Tom and Twilight up with proper dates so they can stop being sad, lonely virgins! I know I’m not Tom or Twilight, but would you mind too terribly teaching me for their sake?” Duskfall grew puppy dog eyes.

“Yeah, sure, I don’t mind,” Bonnie replied.

“I don’t mind either,” Lyra agreed. Duskfall’s face lit up like a firework.

“Thank you so much! I’ll find a way to make this up to you!” Duskfall pronked out of their house, happy as a clam.

“Her Heart is gonna break when she realizes she can’t get them back,” Bonnie predicted sadly.

“You don’t know that’ll happen,” Lyra’s protest sounded weak to her own ears.

“We both know what happened was a one in a trillion freak accident. Even with someone of Duskfall’s no doubt incredible brain power, some things are simply impossible,” Bon Bon shook her head. They had to face reality.

“She’s going to need more than just a good fuck every Friday night or whatever,” Lyra pointed out.

“Do you know what you’re suggesting?” Bonnie asked.

“Hey, my parents already disowned me. They can’t double disown me for starting a herd,” Lyra snarked. Bonnie snorted in amusement.

“They might just take you back if they hear you started a herd with a princess,” Bonnie teased.

“Bleg. Well, sometimes sacrifices have to be made,” Lyra made a face. Bonnie went to nuzzle her marefriend.

“How noble of you,” She quipped sarcastically, “But I agree. We can watch over her and love her until she’s ready to find her own Love.”

“And if she decides that Love is with us?” Lyra wondered.

“I can think of worse fates. If we don’t do this, who will? No one else can do this, unless Fluttershy has been harboring feelings for Tom or Twilight and suddenly decides now would be the best time to act on them. Duskfall said Tom and Twilight were lonely. I don’t think it’s a stretch to imagine she is as well,” Bonnie reasoned.

“And that loneliness might kill her in her heartbreak,” Lyra didn’t want that to happen.

“Then we’re agreed. We love her and protect her in her time of need until she no longer needs us.”

Author's Notes:

Have I mentioned Lyra and Bonnie are best couple? Because they're fucking best couple. They heard what Dusk was getting up to so they came to me and asked me to write up that segment on the end. I just don't have words for how grateful I am to both of them. Duskfall was gonna get real fucked up in the head before they stepped in and contrary to popular belief, I don't enjoy making my characters suffer.

It occurs to me I might have to boot this up to an M...

Are Amethyst and Dinky The Doctor's kids? Are they Loomed? Is Amethyst named after Amy Pond? ...Maybe

Also, before I forget AGAIN (thanks goldfish memory) here's a blog post for a story idea: Silly Idea