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Description

I am truly starting to think she is a time traveler.

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Nyperold

Tickling Pony Bellies
Lyra, Minuette, Bon Bon, and Derpy were all fillies at that party. A Post-Rainboom Event. Yet, all were grown mares at the Summer Sun Celebration that inspired Twilight Sparkle to pursue magic. A Pre-rainboom Event.
 
I have to assume time travel is involved.
youregoingtoloveme

She is a host to a Goa’uld symbiote who is too inebriated at any given time to become a capable System Lord. It is also perpetually repairing the damage Berry does to her liver.
Background Pony #DA26
So, if all the mane 6 got their marks after seeing the rainboom then…
 
I’m curious, if Pinkie had this party with filly Cheerilee, then she would have already gotten her cutie mark from seeing the rainboom. As her first party was with her family on the rock farm.
 
However, in both Cadance/Shining Armor and Sunset Shimmer comics Twilight is cutie markless. Yet we have a fully grown set of ponies in each comic, Cheerilee, Cogate/Minutte, Twinkieshine, Lyra, and so on.
 
So how can they go from fillies (cutie mark Pinkie) to near grown mares (no mark Twilight) if the mane 6 got their marks on the same day?
 
As far as I’m concerned stick with your headcanon ages or we’ll be at this for days.
Background Pony #D4BB
Just how old is Derpy Hooves? She appeared fully-grown in “The Cutie Mark Chronicles” in Twilight Sparkle’s flashback.