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FlurryHboi
Wallet After Summer Sale -

I love Flurry
maverick159
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.

Y'all are stupid!
@larrykitty  
why not both?
Shinkaku
Fifth Yacht -
Diamond Trophy - Are you a TAS by any chance?
Chaotic Little Trees - 1000+ images under their artist tag
Pixel Perfection - I still call her Lightning Bolt
Solar er - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Da Magicks! - Merited Fine Arts badge with only their own art
Fine Arts - Two hundred s with a score of over a hundred (Safe/Suggestive)
Non-Fungible Trixie -
Magnificence - Artist with 100+ Safe/Suggestive images with over 100 upvotes, and 5+ Questionable/Explicit images with over 350 upvotes
Perfect Pony Plot Provider - er of 10+ images with 350 upvotes or more (Questionable/Explicit)

Not...even...once...
@Background Pony #6A6C  
I see Lightening Dust as his girlfriend more, gives is that tusudreXgoodboy vibe
maverick159
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.

Y'all are stupid!
@darknessRising24  
Mine is actualy more simple. Flash and lightning are twins and first base is their younger brother.
 
I don’t know about scootaloo or tender taps but maybe one of them could be a cousin.
 
I don’t think tender taps and scootaloo are related
Alphamon_Ouryuken
Perfect Pony Plot Provider - er of 10+ images with 350 upvotes or more (Questionable/Explicit)
Artist -

Lord of the Empty Seat
@Background Pony #6A6C  
I have my own headcanon for his family as well:
 
Younger Siblings:  
First Base & Scootaloo
 
Cousins:  
Tender Taps, Soarin, Lightning Dust & Indigo Zap (sisters).
maverick159
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.

Y'all are stupid!
@Poptard  
Cool ;)
Poptard
Every pony has fans - Derpi er
Silver Bit -
Diamond -
Wallet After Summer Sale -
Not a Llama - Happy April Fools Day!
Happy Derpy! -
Silver er -
The End wasn't The End - Found a new home after the great exodus of 2012

The Tastiest
@maverick159
 
Weird, me too.
maverick159
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.

Y'all are stupid!
@Background Pony #6A6C  
The headcanon is strong in this one.
 
I also headcanon lightning dust being his sister
Background Pony #B395
I already headcanon Flash Sentry being the older brother of First Base & Scootaloo. Though I never quite thought of Tender Taps being related to them as well though that’s still a great idea :)
 
I also headcanon that Lightning Dust is his sister and Sky Stinger is his cousin.
@Careless Whisper  
I could go with that. On Sesame Street, Elmo’s dad is supposedly in the military overseas somewhere. It’s an unfortunately common enough thing that the MLP show writers could easily include it as a feature in Equestria.
@Careless Whisper  
Of course, you still have to explain why Scootaloo lives in Ponyville and Flash Sentry is stationed in the Crystal Empire. Equestria’s military doesn’t have family moving allowances?
I accept this head canon it would make Scootaloo’s life slightly less sad and Flash Sentry a bit more likeable
Tetrominon
Office Culture - These water cooler conversations sure get heated around here.
Fifth Yacht -
Diamond Trophy - Are you a TAS by any chance?
Solar er - Fought against the New Lunar Republic rebellion on the side of the Solar Deity (April Fools 2023).
Non-Fungible Trixie -
Bronze Bit -
Speaking Fancy - For helping with translations
Happy Derpy! -

Undesirable
@maverick159  
The presence of the word “orange” in the name prevents her from acknowledging its existence on religious grounds.
maverick159
Friendship, Art, and Magic (2019) - Celebrated Derpibooru's seventh year anniversary with friends.

Y'all are stupid!
Yoooooo thats so cute and sweet ^^
 
 
@Background Pony #A120  
How about applejack?
Background Pony #DA53
Even if they are not related, they could form a “League of Orange Ponies”.