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Ponibius


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Princess Twilight Sparkle is asked by Cadance to help with the Crystal Empire’s Hearts and Hooves Day. Heading up north to help organize the festivities, she runs into a problem—that she’s a single pony on the most romantic day of the year.

A Winningverse Story

Chapters (1)
Comments ( 60 )

Yes woo, another great tale!

And here I was kind of hoping that relationship would stay in the past. Oh well. Though I get the feeling that no matter what Storm said.

Some of her reasoning was career over anything else.

Hmm. Some very intriguing history here, from Cadence's involvement in the Zebrican civil war to what became of Sunset in this worldline. The main story is nice, but drags on in places, and doesn't really end so much as it just stops. Still, nice to know what Twilight was doing while Starlight was trying to enforce ehr own version of the holiday... though I don't see the attempt to rekindle this relationship going over well with Cloud's current significant others.

8941081

I will say that part of the purpose for me writing this story is to help set up another story down the line that I should be publishing in the not too distant future if all goes well. Probably in Aug-Sept depending on how my writing and publishing progress goes. I've got some trouble to throw Twilight's way, and her relationship issues being a significant part of that.

I don’t think I have anything clever to say. This was just delightful. Super excited to see where all this goes! I can see Fluttershy being okay with Twilight joining their little family unit, but I’m not quite sure about Blossomforth. Then there is the whole suitor thing, but I can’t see Twilight leaving Equestria. Oh well. Until next time!

Huh... looks like I was waaay off with my thoughts about Storm. I mean, they've been together for a while by this point, and I had always assumed that they had gotten really, really close to one another, with propriety being the only thing keeping them from growing closer, but it seems like I was completely off the mark there. Maybe this is just me reading into things, but I thought there was a certain chemistry between them, and obviously both Twilight and Cadence thought the same thing, so it's a little surprising to hear her response be 'I'm not really interested in mares, I'm not really interested in you romantically, and I'd rather us be kinda-sorta-ultra-awkward-super-formal friends.'

That was pretty much a triple sucker-punch, worse even, because at the end there it felt like Storm was tactfully admitting that they were not nearly as close to each other as Twilight seemed to think they were, and that just hurts you right in the heart. Half-surprised Cloud was willing to hop on the band-wagon considering how fragile her own relationship is at times, but I also got the feeling that back when they were dating that Cloud was really, really interested in Twilight, and not just for sexy-time shenanigans. So I guess it's not that big of a surprise. That said... yeah, Fluttershy and Blossomforth aren't gonna go along with it. I half-remember Twilight having developed a crush on Fluttershy and asking her out only to be turned down, so that's probably a dead-end, and then you've got Blossomforth, who pretty much only puts up with Fluttershy being in the relationship because she knows Cloud is hopelessly in love with her.

So long story made short? Fluttershy isn't interested in Twilight, Blossomforth ultimately wants Cloud all to herself, and neither of them would be willing to add yet another person to their already complicated love-life unless they were absolutely certain it was something all of them wanted. Which it isn't, because only Cloud wants it, and even then, it's not like it was with Fluttershy where she literally couldn't keep herself away from her. There's a pretty hefty difference between really liking someone and being head-over-heels in love with someone.

8941333
Glad someene else finds something up with how Storm did this. There are easier ways to tell Twilight that it could never have been a thing between them.

I can get she was never into mares like that. But now it feels she only cared about herself, and never considered Twilight in this.

Me thinks Cadance will be having a word with her later about it. Goddess of Love and all.

Well...there's not way this will get complicated at all. Nope. At least everyone involved understands the importance of calm, honest discussion. But Cloud Kicker's love life does not have a calm history. With luck though they've moved past the 'relationship drama because of avoidance' phase and into the 'relationship drama because relationships are hard and their lives are crazy' phase.

It's a bit too bad about Storm, but it does make sense. And there's more than one kind of loyalty and devotion.

And I admit, I'm a terrible sucker for Sunlight. If there are sparks with Sunset and Twilight, well, it's not what I'm expecting but I can't say I'd mind...

Also, any chance we'll get the history with Cadence and Zebrica? Because I'm intrigued.

Huh... Well, this really went in some surprising directions. I certainly didn’t expect the possibilities with Storm to dry up quite so fast and cleanly. While it’s quite possible that she wasn’t being honest with herself or Twilight when she claimed to not be interested in her princess that way, the scene still felt like a sincere effort to take that option off the table for the future. I really hadn’t seen that coming.

As for rekindling things with Cloud... hmmm. If I’m being honest, she is by far the least interesting option out of the entire Winningverse cast, to me. For one thing, I never personally cared much for the whole polyamory thing to begin with, and Twilight being one of Cloud’s three (four, if you count Derpy) “special” someponies just does absolutely nothing for the romantic side of me. I’ll try and keep an open mind as this leads into whatever story you want to tell next, though.

Cloud whispered something to Storm I couldn’t make out over all the noise of the crowd behind us. Storm nodded to her cousin and spoke to me with a gentle tone. “I am sure she can find it on her own, Highness.”

The things I picture when I take a couple lines of a Winningverse story out of context...

Ponibius and Chengar will look up and shout: "stop shipping Twilight and Storm."

And I'll look down and whisper: "no."

Ohhh this was cute! And has me looking forward to Sunsets adventures even more with how much is moving towards Freeport.

Also future Twilight relationship stories sound realy apealing.

8941333

Have to agree with everything here. I haven't dug into the Freeport business yet since 'rogue-ish exile' is in no way my style, but I've always been a fan of SunLight, so maybe there's hope there. Almost anything is better than a political marriage.

Honestly I find 'Zebrican sultan' to be a bit odd, since we have Saddle Arabians representing the Middle East, and the Zebricans representing Africa. I know there were several sultanates in Africa in history, but the general representation blindsided me.

Aha! Confirmation! Sunset is the Archon!

8942183
Go right ahead. Despite how this story played out, I’m not averse to pairing them off. It’s just that between all the complicated baggage of Storm technically being Twilight’s subordinate and the likely effects on her career, plus her being mostly straight, it’s not something she’s inclined to pursue. Remove or modify one of those factors, and...

8941327

I can see Fluttershy being okay with Twilight joining their little family unit, but I’m not quite sure about Blossomforth. Then there is the whole suitor thing, but I can’t see Twilight leaving Equestria. Oh well. Until next time!

Fluttershy and Blossomforth are definitely going to have their own opinions on this, especially considering their own histories with Twilight. And the suitor thing is also going to be an issue when I get to that next big Twilight story I plan on writing in the near-ish future.

8941333

Maybe this is just me reading into things, but I thought there was a certain chemistry between them,

They do get along. One thing to keep in mind is that what Storm says isn't necessarily what she's thinking, and Twilight isn't the best at reading others. Of course, she does let duty get in the way of what she might be feeling, being hidebound by what she feels is right and proper. Then certainly Twilight and Cloud are going to have several things to work through if a relationship between them is going to work.

8941687

Glad someene else finds something up with how Storm did this. There are easier ways to tell Twilight that it could never have been a thing between them.

Storm's formality and adherence to duty are probably her biggest hurdles to having a relationship with Twilight. They definitely get along, though what Storm's really feeling versus what she said...

8941827

And I admit, I'm a terrible sucker for Sunlight. If there are sparks with Sunset and Twilight, well, it's not what I'm expecting but I can't say I'd mind...

Also, any chance we'll get the history with Cadence and Zebrica? Because I'm intrigued.

I will say that Twilight and Sunset are going to get to meet in a couple of stories I will be releasing in the near-ish future. So you will get to see how that plays out in the long term.

And yes, the history of Cadance and Zebrica will be covered in a future story, though that one might take a while to get to.

8942037
This isn't the last word on Twilight's relationship stuff, more just me prepping the way for another longer end story I'm going to be writing for Twilight here before too long. There's plenty of exploring of relationships that needs to happen before anything settles.

8942183
I haven't said yes or no to anything yet.

8942188

Also future Twilight relationship stories sound realy apealing.

I've been thinking about this story for a good while now, and I'm hoping I can deliver on something entertaining for everyone.

8942260

Honestly I find 'Zebrican sultan' to be a bit odd, since we have Saddle Arabians representing the Middle East, and the Zebricans representing Africa. I know there were several sultanates in Africa in history, but the general representation blindsided me.

While nothing is a one-for-one comparison, the Zebrican Empire in the Winningverse draws heavy inspiration from the Ottoman Empire, which was based out of Turkey (and at its greatest expanse controlled much of North Africa, the Middle East, and the Balkans).

Really not trying to be a downer here but man, I loved Twistorm, and seeing it blown up here in favor of the least interesting part of Study feels kinda lame.

Agreeing with 8942037, the scene felt it came to a firm conclusion about the unlikelihood of any romance between the two, which just seems odd with all the hints building them up so far.

If it's meant to build the foundation of future arcs it feels kinda weird to have such a sharp shift in trajectories. But I'll try to work past my personal disappointment and see if it's satisfying in the end.

Cloud's kid is how old? And she wants to add relationship drama to that? This'll be a mess.

8942355
I sorta figured there’d be some complications with that possibility, and naturally Twilight has to at least meet some suitors regardless of whether she stays with any or not. Guess that means we all just have more to look forward to!

8942336

8942355
I didn't think you two were actually saying no to anything, nor would I mind if you were (I am not an invested shipper).

Just making a dumb little joke.

Huh. I thought there had been some StormxTwilight ship teasing back in some of the older fics. Guess I misremembered them.

Still, I'm down for Cloud and Twilight again. I enjoyed Study for that purpose. They played too well off of each other.

8942355

Works for me. I don't have any sort of problem with it, just wasn't expecting that particular link.

8942336
The thing with her being concerned about her career (aside from the fact that she may or may not be fully straight as she thinks she is), is the fact that Storm is blatantly ignoring something obvious.

Cadance and Shinning Armor were once in the same boat as she and Twilight, and look what happened.

8942857
To be fair, Shinig did come from a slightly more privileged position than Storm as a potential Duke, and he did apparently have ponies who doubted the legitimacy of his becoming Captain of the Guard.

8943053 8942857

More directly, considering that the Kicker clan were always in favor of Tornado being Captain of the Guard, I wouldn’t be surprised if the general attitude in her own family was that Shining got his post by virtue of his relationship with a Princess, rather than by merit. Storm herself may have held that belief.

Which would make pursuing a princess now either a sign that they were all wrong/hypocritical, or that she really is trying to sleep her way to the top. It wouldn’t be just the clueless opinions of others that she would have to ignore, it would be the stance of her own family.

8943090
That was something I was thinking about, but didn’t know how to explain.

Gonna be honest, bummed Storm said what she did

I always see Twilight's interests going a bit towards xenophilia. As her only canon interest was some bald ape creature belonging to some fascinating new culture. Some charming, erudite, somewhat awkward being; zebra, griffin, donkey, dog, or now hippogriff, yeti or cat. Though this is a different universe than show canon, no EqG and no Flash.

Gotta admit, I didn't see Princess Books and Cloud as a serious couple, it seemed (what little has been shown) like it was more casual. You've got a plan though, so I'm curious.

Princess Twilight Sparkle is asked by Cadance to help run Hearts and Hooves Day in the Crystal Empire. Wanting to help Cadance run one of the greatest holiday events of the year, Twilight agrees and heads north to help organize the festivities. Though it’s not before long that she runs into a problem—that she’s a single pony on the most romantic day of the year.

Your description is very wordy. It can be trimmed down quite a bit without losing much.

Twilight heads north after agreeing to help Cadance preside over the Crystal Empire's Hearts and Hooves Day. It's not long before she runs into a problem—she's single on the most romantic day of the year.

A look into the actual story reveals that this is an issue all throughout. Twilight tends to ramble in frustrating ways and she has a lot of "no shit" moments. I highly suspect that some tightening can drop the word count to 10-12k.

JMP

Would have liked to see Sunset meeting Twilight for the first time. Considering how she acted towards Cadance way back in "A Moment in the Sun", I wonder if there was any resentment Sunset had to work through. I mean, not only Celestia take on another personal student, but that student became an Alicorn Princess. Maybe Sunset got it out of her system beforehand? Either Twilight is really bad at reading people, or Sunset's matured a hell of a lot, and has matured even further compared to the point in the timeline of the Venture stories.

8944040
Well, her maturing IS kindof the whole point isn't it?

JMP

8944117
That's true, and we've seen a great deal of it in Sunset's stories (they're among my favorite in the Winningverse, along with all the Lunar Rebellion stories). All I'm saying is, meeting Twilight, the prodigal alicorn princess student of Princess Celestia, is a major point in the maturation and development of Sunset's character that I really hope to see first-hand. Still got a long ways to go, probably. Will be interesting to see what comes of The Northern Venture.

8944121
Definitely, I'd love to see how that interaction goes and what she thinks about it. At least she'll probably have heard what Twilight and the others have done. I might actually see her taking it two different ways. She could go 'ANOTHER one?!?' and be jealous. But I could also see her thinking that Twilight did what she was originally trying to do, only she actually succeeded at it. And that would be a much more complicated and interesting mess.

JMP

8944139
Though all this begs the question, how far back are the Freeport Venture stories anyway? Just how much older is Sunset compared to Twilight?

8944158
No idea. As a rule I imagine Sunset in her 30s while Twilight is in her 20s as long as it makes sense, even if it often doesn't.

8944010
I'll see what I can do about trimming some of that fat to make things more streamline.

8944229
If you want, though I honestly didn't mind it at least. The story seemed to take it's time but it was a fine trip. Whichever works for you.

8942546
Nah, I figured you were joking. It's all good.

8943053
8943090
Everything that happened with Shining and Cadance, and the Kicker Clan's reaction to how they perceived Shining got the title of Captain of the Royal Guard. Little surprise she might not want to get into the same trouble, even if it might only be subconscious. There is also the fact she's had a number of things dumped on her with Cloud dropping out of the Guard and how she's now set to become materfamilias of the clan after she donned Shadow's Armor.

8944121
8944139
The good news is that you won't have to wait that long to see a Sunset and Twilight meeting in a story, and see how they'll interact.

8944158

Though all this begs the question, how far back are theFreeport Venturestories anyway? Just how much older is Sunset compared to Twilight?

Sunset is about a decade older than Twilight, Darkstarling's age guesses are pretty much right.

Well, that was enjoyable.

Nali #39 · May 27th, 2018 · · 2 ·

...

Man, I know dry discussions about pragmatic concerns are a Winningverse staple, but everyone involved in this feels like they're negotiating a business arrangement instead of talking about love.

I stroked my chin as I came to a conclusion. “Perhaps we can put out feelers to Zebrica and Westmarch and see how they respond. There isn’t any harm in keeping my options open until a decision has been made.”

Christ.

And then there's the idea of picking things back up with Cloud, which is flagrantly and obviously a complete minefield and nobody has an issue with it? At all? Just, "oh, but only if the other two girls you just had a baby with are down"? Even by this universe's more lax social norms, trying to wrap my head around the thought process here is genuinely giving me a headache.

Nobody feels real. The only feeling I get out of Twilight is obligation, the Princess of Love is encouraging arranged political marriage and intruding on an existing love polygon with a kid involved without even mentioning the rest of Twilight's plethora of friends as a possibility, and Cloud seems to have forgotten two novels' worth of getting her life under control. Storm comes off the best, and that much only because she's already taciturn and a lack of emotion doesn't seem unusual.

I'm not looking for an out and out shipfic here, but there's no romance to justify that tag either. Presumably you're going somewhere with this in time, but as a standalone story it's unsatisfying, and as the setup for something else, I'm left with a lingering sense of dread because I don't want to see any of what's been set up here come to fruition.

I hate leaving harsh reviews, but I can't remember the last time I bounced off a fic so hard from a writer I otherwise enjoy.

Ugh, the dread return of potential TwiCloud. Still makes no sense, do not want.

Q07

8941103

another story down the line

trouble to throw Twilight's way

her relationship issues being a significant part of that

Oh no, please, I don't know if Twilight can handle the complete emotional turmoil of another story about her and relationships.

I was really hoping for something between twilight and storm. Cloud did say she doesn't 'usually' go for mares. They seemed like a fun match. I don't see it getting serious with twilight and cloud though. I would like cloudverses twilight to find someone suitable for her.

8941103

I will say that part of the purpose for me writing this story is to help set up another story down the line that I should be publishing in the not too distant future if all goes well. Probably in Aug-Sept depending on how my writing and publishing progress goes. I've got some trouble to throw Twilight's way, and her relationship issues being a significant part of that.

I think that had this comment not been here to confirm it, I would already suspect this was merely to set up a future story. I don't mean that in a good way.

This didn't feel like a story at all. Stuff happened. "Conflict" was so thin as to be nearly non-existent. I'd say this was more prologue material, and honestly I wonder why it is its own story (as in, published as a stand-alone fic).

I'd be tempted to say this collection of horsewords doesn't exist in part to set up the real story still yet to come, but technically a could of other items compete with that to give this some purpose:

I was originally a fan of Storm Kicker (and Star Kicker) from Thrilling Investigation. I have grown to utterly dislike Storm in every installment of her character arc in Ponyville as Twilight's guard, any implication that she and Twilight would become romantic, or any of her involvement in any plot or action. You'd think I'd be cheering that this story is WV canon putting a stake in the heart of that foul ship, but even with me being fully on board with sinking it, I find the proposal and rejection of a relationship between Storm and Twilight to feel gratuitous. It was an item to check off a list, and of no more consequence than the lists used in-story to organize these holiday celebrations. I'd agree to toss it in the garbage alongside them.

On the other side, from Study's early days, I had been pretty keen on Cloud and Twilight hooking up. Though, like many others, I found the execution at the end rather lackluster. I wouldn't go as far as Morion87 to say I'd hoped it would be forgotten. Instead, I've been entirely disappointed that neither Cloud nor Twilight seemed to indicate at all that there ever had been anything between them in any of the post-ascension Twilight WV stories. That that relationship has felt like it was forgotten about until now has been more of an issue for me.

Some speculation on the real story that this prologue hints at:

Twilight's original attempt to ask Fluttershy out, then her less than smooth interactions in New life, and now potentially seeking to join their relationship sounds like a whole mess of drama waiting to happen. Seems like a good hotbed of storytelling to jump into then sort out.

Blossom, as usual, will probably be mostly forgotten about, pushed to the side while the "more important characters" do their story thing. Then the story will remember she exists at the end and just kind of shoehorn her back in awkwardly. That's how it went in Life and Times, Study, New Life... fourth time's the charm for Blossomforth maybe?

Back to this "story."

The only emotion this whole "story" managed to convey at all was embarrassment and awkwardness. Strictly by telling us that those emotions were happening. Outside of being told that little fact of the world, this was a tedious walk through a "this happened, then this happened, then this happened." There was a very tiny bit of effort to show Twilight being "helpful" and obsessed with organization. I guess that counts as characterization. There was a very tiny bit of flirting with Cloud, which Twilight was receptive to. But it all came across incredibly wooden and forced.

I think Storm Kicker's POV would have been more appropriate. Maybe from Maud Pie. This felt as deadpan as either of those two.

Much like I can't say this had only one purpose while being technically honest, I can't say this story entirely lacked a plot either. Technically it has one. Twilight isn't sure how to go about having romance, but one talk with Cadance and she has to figure it out for herself and just try. She tries with Storm, and Storm turns her down. She asks Cloud, and Cloud is willing to give it a try, though that will have to wait for the real story when her two wives are consulted on expanding their lovepile. There is never any sense of real opposition to anything happening. A question is asked, it is answered, and the answer is immediately accepted in all cases. That one of the answers is a decisive no kinda sorta feels like conflict-ish.

There is no sense of payoff or climax to the story. There is no rising tension of any sort. There is no strong link to the holiday or setting. You could strip out all of the setting details and just have these conversations happen any day of the week in Twilight's castle, Sugarcube Corner, or whatever. The activities going on have no impact on the conversations.

You could just delete many of the conversations without changing the overall "story." Delete the conversation with Cadance that leads Twilight to decide to just think it over and try it? She could just do that on her own. Nothing especially insightful came from it. You could keep that, and just skip/delete the stuff with Storm. Leaving that one uncertain and to be possibly dealt with after the much more complicated stuff with Cloud and Cloud's existing relationships would still feel about the same. Put Storm's stuff back in, and just end it there leaving us on Uncertain terms concerning Cloud and her already existing relationships would still be leaving us off wondering until the real story hits.

Hell, you could just delete the entire story and literally summarize things in the form of that real story's prologue. Picture this:
The first line of the said hypothetical prologue is Storm turning Twilight down. Twilight and Storm decide to remain friends, Twilight is ever so slightly glum about that. Next scene, she's talking with Cloud. She explains a bit about why she's asking, we get a short version recap of the (now deleted) bits with Cadance, and we end the prologue with Cloud and Twilight on a sort-of date and ready for chapter 1 when talking things over with Blossomforth and Fluttershy is possible. Cutting out as much of the leadup and background details of this story to shorten it down to a few thousand words instead of fifteen thousand-ish would serve as a quick, informative, and potentially attention-getting prologue.

So, in the end, stuff happened. You can only care because you're invested in the WV continuity, and this checks off some boxes. It's a prologue, not a story. For years now I've been of the opinion that Ponibus writes more interesting WV stories than CQ does, but with Study finishing with a whimper and now this, it feels like what makes the WV bad in CQ's stories is starting to impose itself upon the Ponibus side of the 'verse.

I chuckled as well. “Shining can be a bit dense.

Cadance let out a resigned sigh as she rubbed her forehead. “What kind of stallion answers ‘Would you like to come in for coffee?’ with ‘I dunno, it's so late I'll be up all night.

To be fair, he isn't exactly alone with that problem. Remember the story that started this whole universe. :rainbowderp:
Starlight was even worse because Trixie can't spell subtle with a dictionary. Hay even the self proclaimed "making love expert" herself took months to realize Blossomforth was in love with her. :facehoof:

And Twilight shouldn't judge, she spent years thinking that love and romance was something that only happened to other people. It took Cloud, and all of her friends months to convince her that someone might want to have a relationship with her that wasn't an arranged political marriage. And it wasn't even until after she found out her parents had done the same that she actually dared to try dating for herself. :facehoof: :facehoof: :facehoof:

Despite being head over hooves in love with her, my big brother had taken years to bring himself to actually ask Cadance out on a date. Successfully, anyways. There was one instance where he somehow managed to convince Cadey he was gay when he tried to ask her out. That was a level of failure that made me feel a little better, though a part of me couldn’t help but wonder if our co-dating issues was genetic.

Nope.:rainbowhuh:
It doesn't seem like your parents had any problems finding love, since both of them did it, twice. They both managed to keep their marefriends on the side AND have a happy marriage with each other. That's not an easy thing, so credit where it's due. :moustache:

Still, I find it adorable that Twilight keeps getting turned down again and again. She may be the princess of platonic love, but she has no luck with romance. She seems destined to keep getting turned down by ponies she has an interest in. First there was Fluttershy, then Celestia, Storm and then Cloud ... wait Cloud didn't reject her ... and she's only asked four ponies out in how many years?! That's actually a pretty good success ratio as far as asking people out goes. Of course she would get a lot more positive results if she tried asking a bit more often, dating is often a numbers game. You'd think someone as smart as Twilight would figure that out. Hay there's got to be lots of single mares in Ponyville alone, Derpy for one. Go on a few dates, with different ponies and find out if it might go somewhere. You don't have to already have a crush on someone to ask them out.
P.S Kukri Doo might still be single, just saying. :raritywink:

8944158
I'd like to know that too. At first I assumed it was at least 20 years between Freeport and Winning Pony. Given that Freeport happened befor Twilight got her cutie mark (possibly even before she was born) and she seemed to be in her late 20:s in Winning Pony. Since Sparkler was thinking about going to college at 18 years old and Cloud did 4 years of college and had lived in Ponyville for 7 years. That'd make her 29 in Winning Pony. Cloud, Fluttershy, Rainbow Dash and Derpy are all roughly the same age. Give or take a year. I assumed that all of the mane 6 are all roughly the same age as well since they got their cutie marks together.
(Though if the authors want to go with a few years age difference between the mane 6 I'd roll with that. If Fluttershy got her mark at age 13 and Dinky at age 8 then there's definitely some wiggle room.)

Now I'm inclined to think it was less than the 20-30 years I first assumed. For one it's hinted that the Kickers started attending West Hoof at a younger age and that the mane 6 were older than I assumed when they got their cutie marks.

For a minimum age difference: Sunset left Celestia at age 17 and Twilight entered Celestias School at age 13 less than a year later. But I think it's definitely a bigger age gap between them than that.

For one: Sunset is still in her teens in Freeport yet she considers Starlight to be young and immature. And Starlight comments that she is older than Twilight by a good number of years.

Lastly: Teenage Cadence is foalsitting for toddler Twilight. Meaning that, unless Alicorns age slower than normal ponies, Twilight can't be much more than a decade younger than Cadece. And I don't remember Cadence being significantly younger than Sunset.

This is all speculation of course but my estimate is that there's a 7-20 year age gap between Twilight and Sunset. (My best guess, around 15 years.) But remember that Twilight is older in Winning Pony than Sunset is in Freeport. Sunset can't be older than 19 since she is called a teenager, while Twilight is well into her twenties, possibly even 30 in Winning Pony.
That adds another 2-10 years (Depending on how old Twilight is) between Freeport Venture and Winning Pony.

Huh, maybe my gut instinct of 20 years wasn't so bad after all.

JMP

8975807
Eh....Ponibus already replied that Sunset was ~10 years older than Twilight. So it does fit into your estimate, though you didn't need to go that in depth.

8975857
I guess I missed that, thanks.

Still analysing is fun, and sunbathing without anything to occupy your minds is boring, so I have no regrets!😎

Hay there's got to be lots of single mares in Ponyville alone, Derpy for one.

And by dating Derpy she can continue the Sparke family tradition of giving Derpy a child.

This was good and an enjoyable one to finally getting around to reading. That being said though one thing does keep grabbing my attention. This is not the first story from either Chengar or Ponibus that mentions Sunset becoming Archon and basically in charge of Freeport but as far as I'm aware we still don't have an actual story where and when that happens. Maybe someday?

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