Crazy Headcanons

@HJSDGCE  
Went Pinkamena for months until the Cakes hired and “adopted” her.

Queen Chrysalis expected Twilight to shoot first and ask questions later when she found Cadance in the caves,which would not only take care of a loose end she hadn’t quite gotten a chance to tie up, but would give her leverage on Twilight should she ever resurface.
 
Princess Luna knew about Diamond Tiara’s issues long before anypony else, for obvious reasons, and is getting real sick of Spoiled Rich’s shit.

@Scrounge  
Eventually, Luna presses charges and implements a restraining order.

@Wiimeiser  
We can only hope.

Sombra and Shining Armor would made for a great Solid Snake/Otacon like friendship/cooperation if they were on the same side.

Lemon Hearts, Lemon Zest, and Lemony Gem are all not-particularly-distant cousins. However, in both Equestria and the human world, they have not met and are at most vaguely aware of each other’s existence.
 
I can’t remember if I’ve said something like this before, but… Back when she was Special Agent Sweetie Drops, Bon Bon often crossed paths with Ahuizotl, and in fact was his most frequent foe other than Daring Do herself. Eventually, the agency was shut down, and it was years before he tracked his old foe down to Ponyville, intent on finding out where the things she had confiscated from him had been sent. Unfortunately for him, Bon Bon wasn’t home. More unfortunately for him, Lyra was. He barely escaped with what little dignity he had left, and to this day, high-pitched fangirl squealing noises make him very, very nervous.
 
Since the Fall Formal all the way up to (and past) the Friendship Games, Sunset Shimmer has given many reasons for not returning to Equestria, some better than others. These include,but are by no means limited to, the following, in approximate chronological order:  

Much like how Nightmare Moon inspired the Equestrian “halloween” equivalent Nightmare Night, Discord is or will be the inspiration for Equestria’s “april fool’s” equivalent holiday.

The reason Pinkie is so flexible now is from a Nightmare Night prank gone wrong involving her sister Maud and a very well-made dragon suit.
 
Her skeletal structure never grew back properly.

Cotton Cloudy is actually quite butch and tomboyish. In contrast, Rumble is surprisingly feminine. In spite of this, they’re both straight, and in fact end up together.

@Wiimeiser
 
I like it! Headcanon accepted!

Griffons have a sexual preference toward other avian creatures. While in general they prefer mating with other griffons, of the pony races, they prefer pegasi.
 
Also, they’re known to sometimes mate while flying.

It is impossible to steal cake from Celestia.  
She is connected to the Cake Force.

Filthy Rich has a passion for fine Coltban cigars.

@Crystal Neighybánya  
But sometimes he wants to have fun, at other people’s expense.

Spoiled Rich and Berry Punch are drinking buddies.

@Crystal Neighybánya
 
Of course, Spoiled buys the most expensive stuff in the house, even if it tastes like swill. If she’s already had a few, she then announces it to everypony else in the bar and proceeds to pour half of it into her mouth, spilling it everywhere.
 
Berry Punch, being saner and altogether less of a bitch, buys what she likes.

@Crystal Neighybánya
 
@YetAnotherBrony
 
So really they’re more like drinking frenemies.

(Slightly NSFW)  
Sunset Shimmer is actually Celestia’s bastard child from Starswirl the Bearded.

@atalarikt
 
And that would make Sunny Shim how old?

The Equestrian Games featured quite a lot of political controversy as it was decided that Ponyville was to be allowed to have the most medals in order to gain exposure for it and it’s new Princess. This didn’t sit well with quite a few ponies, which is why all of their teams were switched at the last moment to compete in areas they had no experience in while the racing team was assigned mediocre, downright flight-crippled athletes, making the whole harder to conceal.
 
The Wonderbolts, as expected strongly disagreed with the trickery and cooperated with the Ponyville team leaders to get Rainbow Dash to switch teams so that with Derpy, Bulk Biceps and Fluttershy competing against them, it would be plainly obvious that the whole thing was rigged. Sadly, the Mane 6, which were kept out of the loop got themselves involved and prevented a perfect showcase of the corruption involved.
 
Their plan still worked out in the end, as many questioned just how was Ponyville able to win on the medal count while so many of their athletes obviously weren’t in their respective field of expertise. Celestia had to get quite a few parties involved to cover up the whole controversy, especially the parts involving Twilight and claims of nepotism.
 
Wind Rider was one of the most vocal on that affair, seeing the team he so loved accept to take part in such shameful display, framing Rainbow Dash was a win/win situation, as in any case, he no longer wanted to be seen as part of the Wonderbolts.

@Poison Trail  
#Tyrantlestia

@Crystal Neighybánya
 
Not really, I’m a big fan of Celestia, but even I have to admit that a lot of things are way too convenient to not have been orchestrated by her. Not a tyrant, but very much making sure to spoil Twilight in every way imaginable, as can be expected of someone which waited a thousand years for her arrival…. errrg…

@Poison Trail  
So just your usual complaint about everything in the series revolving around Twilight Sparkle in headcanon form?

If Sunset Shimmer ever encounters her human counterpart, it will not be on friendly terms. Human Sunset possesses the inquisitiveness of Human Twilight, coupled with the callousness and deceit that defined our Sunset prior to her redemption; she was “encouraged” to transfer out of Crystal Prep due to an interest in the paranormal and a moral compass that didn’t exactly point north even by Principal Cinch’s standards (take a second and let that sink in). Much like the other Equestria Girls, she is more or less what her equine counterpart would be had her meeting with Twilight and the friendships that followed never occurred, which in this case means she continued down the path of darkness at a slow but steady rate. She firmly believes that knowledge is power, and fervently seeks to accumulate both. She is particularly interested in recent goings-on at Canterlot High… But thankfully, she’s yet to discover who it was that started the chain of events which so intrigues her.
 
A week or so after the Ponyville Days festival, Rarity sent Trenderhoof a dead fruit bat in the mail. Applejack was more than happy to provide the dead fruit bat once Rarity told her what it was for.

@Crystal Neighybánya
 
It also explains how Ponyville’s worst flier and one that can barely fly at all were able to actually win against a team of professional fliers. I prefer that over saying that RD is SO fast that she was able to make up for her 2 teammates by herself and match up with Spitfire, which should had already passed the finish line while Bulk Biceps was halfway through his part.