Crazy Headcanons

Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
Trixie once pulled Angel Bunny out of her hat. He tied her to a chair in front of the whole audience and took over her show. Then he sent her a copy of the newspaper review that said his show was better than hers. To this day she can still hear somepony saying “Not much of an escape artist, is she?” when she’s lying awake at night.
Background Pony #9B26
Rarity keeps little souvenirs of all her previous lovers, most of whom broke up with her when they found out she was stealing their odds and ends to keep as souvenirs.
Alternative crazy thought… Rarity is the only one of the group who has never been on an actual date, since she is usually too busy with her work to find the time to do so. She pretends she dates a lot out of embarrassment, and fakes her expertise on the matter using information she picks up from trendy magazines and the tidbits of gossip she overhears from the customers at her boutique.
 
Also, the souvenirs are all ones she’s bought for herself. It’s not something she’s particularly proud of.
 
As for the others…
 
Twilight went out a few times when she was still in school, but never had much success because none of her companions appreciated her bringing a checklist detailing conventional first date activities, or signing a waiver to allow Twilight to use the data from their outing to determine the “optimal date paradigm”. She eventually abandoned that line of research as an unnecessary waste of time and resources.
 
Rainbow Dash dated back in flight school a few times, but never got too serious with anyone because her focus was always on improving her flying abilities. It’s still something she thinks about very little, and doesn’t care much about either way.
 
Applejack hasn’t dated since before her parents died. Like Rarity she is too busy with her profession to really have the time for such things, but given the large nature of the (extended) Apple family and her desire to pass Sweet Apple Acres down to her own children someday, it’s something she thinks about quite a bit.
 
Pinkie Pie has dated every eligible stallion (and a fair number of the mares) in Ponyville at least once. Not for romantic reasons, mind you, but as a means of gathering additional information for the files in her secret party planning room. Pinkie herself expects to wed whomever is selected for her by the pairing stone, as her parents did.
 
Fluttershy has actually dated more than any of her friends (except Pinkie Pie). She was asked out quite a bit back when she was still doing modeling for Photo Finish, and more often than not wouldn’t say no out of fear of hurting someone’s feelings, or because she was too timid to do so. As a result she’s acquainted with almost half of Canterlot’s extraneous nobility, and a fair number of the richest and handsomest stallions there.
Background Pony #9B26
Pinkie is what you’d call “fun-sexual” (a term she herself made up).
 
I actually always pictured her being a bit more conservative in that department, given her family and background. That being said, however, “fun-sexual” certainly sounds like something she’d be. She does seem like the type to support a “up for it as long as everyone involved is enjoying themselves” mentality.
Scrounge
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Since the Beginning  -

nobody's favorite
Pinkie is what you’d call “fun-sexual” (a term she herself made up).
I actually always pictured her being a bit more conservative in that department, given her family and background. That being said, however, “fun-sexual” certainly sounds like something she’d be. She does seem like the type to support a “up for it as long as everyone involved is enjoying themselves” mentality.
 
I think her background would make her less conservative, as it would mean she probably just learned “don’t do it at all”, and once she moved past that she would have had no idea what the rules of romance and sexuality were for Equestrian society in general, nor would she be likely to follow any rule that she felt did more harm than good (unless it was something officially enforced or she personally knew and trusted whoever made it).
 
So, to recap, she’s learned that this is something that can make other ponies happy, and she hasn’t learned shame or moderation. I think we can all imagine where that would lead.
 
@Shepherd  
That part, they can grudgingly live with. It’s when she tries to get them to read her stories that there’s a problem.
 
@Background Pony #D27A  
Rainbow Dash dated back in flight school a few times, but never got too serious with anyone because her focus was always on improving her flying abilities. It’s still something she thinks about very little, and doesn’t care much about either way.
 
I dunno. I can’t help but think that Dash secretly takes love very seriously, and is super committed to any relationship she’s in. (She does represent loyalty, after all.)
Jarkes
Elements of Harmony - Had an OC in the 2022 Community Collab
Twinkling Balloon - Took part in the 2021 community collab.
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Magical Inkwell - Wrote MLP fanfiction consisting of at least around 1.5k words, and has a verified link to the platform of their choice
Not a Llama - Happy April Fools Day!
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
Thread Starter - Transformers Thread

GOKAAAAI... SILVER!
Pegasi take family very seriously. For any member of their family to tell them, “I hate you,” is one of the worst things imaginable to them. As such, that phrase is not thrown around lightly, and to cut themselves out of a family member’s life is considered one of the worst punishments you can give them.
 
(…This sounds very awkwardly worded, but I don’t know how to word it better)
Scrabbleman
Duck - He literally asked for this
Wallet After Summer Sale -
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Artist -
Birthday Cake - Celebrated MLP's 7th birthday
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
The End wasn't The End - Found a new home after the great exodus of 2012

[screams in German]
Rainbow Dash actually graduated college with honors. She also has two Masters and a PhD, plus she even won multiple science awards.
 
It was only because her dad wouldn’t let her pursue her dream to become a Wonderbolt without a doctorate. Though, she probably needs that Master degree of hers to become Captain anyways.
Random-Rambling
Pixel Perfection - Hot Pockets Spotted
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!

tinyurl.com/dymbb3a
@Jarkes
 
Probably why Mr. and Mrs. [Fluttershy’s parents] let Zephyr Breeze mooch from them for so long. If it wasn’t for Fluttershy, he’d still probably be a hikikomori.
 
Yes, I headcanon pegasi having some Japanese influences.
DanielTepesKraus
Greatest Poster in the Board -
GREEN - TALK TO ME
Roseluck - Had their OC in the 2023 Derpibooru Collab.
Elements of Harmony - Had an OC in the 2022 Community Collab
Twinkling Balloon - Took part in the 2021 community collab.
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
My Little Pony - 1992 Edition
Wallet After Summer Sale -
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends
Equality - Was more equal than the rest of the people during the event and did the only smart thing: wasn't there :^)

will return
rainbow dash is a man. she’s not actually crossdressing or acting or even intently decieving anyone. everyone just assumes he’s a woman, and he’s too lazy and disinterested to correct them.
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