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Description

Because it amused me. Deeper reason there was not.
 
The criterion was “What faction might they join if they popped up in Sigil, had to stay there for a while, and realized you should probably sign up with a faction if you’re going to be getting things done around there?”
 
Yes, other matchings could be made. Pinkie could totally be a Sensate. Or a Cipher. Applejack could certainly be a Godsman, putting in her hours in the Foundry. Et cetera.

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mathprofbrony
Nightmare in the Moon - Had their OC in the 2024 Derpibooru Collab.
Solar Supporter - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
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
Wallet After Summer Sale -
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Birthday Cake - Celebrated MLP's 7th birthday
The End wasn't The End - Found a new home after the great exodus of 2012

@Background Pony #F459
 
Hm. She took lessons in assertiveness, and learned the lesson well enough to integrate it to the amount she desired. She was afraid of singing in public, but overcame her fear. Being shy doesn’t mean you’re not trying to improve yourself.
 
But hey, who do you think she’d be better with? I was trying to think of a faction that makes any point of caring for animals and didn’t really come up with one. (The Wilders are a Beastlands sect.) The Godsmen at least think you could have been one in a past life.
Background Pony #BB4F
The Godsmen preach self-improvement. Fluttershy doesn’t believe in it at all.