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Background Pony #D729
@Baskerville3  
@HJSDGCE
 
WARNING: Wall of text and a lot of speculation.
 
This comic came out before “Amending Fences” and “Party Pooped”, they couldn’t have known back then. Also, it’s possible that Twilight is older than some of the Mane 6, and that the “School for Gifted Unicorns” (or whatever it was called), is an entirely different school as the one she visited at the beginning of the series, which seemed to be some kind of college or university (at least to me), so she still had to go through gymnasium or another school and make good enough grades to qualify for university. Or maybe the School for gifted Unicorns has an extended grade, which means she will stay for another 3 or 4 years at that school, while the Gymnasium is the basic higher school. We have the same with Gymnasiums in Austria, which is either 4 or 8 years (4 years middle-school grade instead of Hauptschule, our common public middle school, and 4 years higher school grade).  
If the age difference between Shining Armor (and Cadence) and Twilight was 3 or 4 years, it might still be possible. Minuette could’ve been 1 year older than Twilight, but had to repeat one year, or Gymnasium is longer than the extended magic school, which means both Twilight and Minuette would start at the same year at University. And Moondancer was simply retconned.
 
I wasted way too much thought and time on this. Does even that make sense?
Background Pony #AE24
So Twi and Minuette went to school together. Minuette ( And possibly Twi) are in the same school year. The mane six are all around Twi’s age as far as I know, so yeah Soarin’ isn’t too old for Dashie.
Baskerville3

sooooo, either lyra, thunderlane, minuette, and caramel, are older then the mane 6 by some extent, or they skipped a few grades. cuz i mean they should be around the age of the mane 6. but then again what are pony ages like?
Ardashir
My Little Pony - 1992 Edition

Did anyone else notice all the honors Cheerilee has listed here – and yet she ended up a school teacher? In Ponyville? I have to wonder how her career went that badly wrong, the poor mare.
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]
Everytime I look at this cover, my head explodes from all the confusion of what age Cheerilee is.
 
She might still be a filly when Rarity gained her cutie mark, and then gratuated a few years afterwards by skipping a year or two.  
Besides, this picture probably happened a few years after the whole “Mane 6 gets their cutie mark” scenario.  
Big Mac probably gratuated after Cherilee, since he’s older than Applejack. And don’t bring the part where he looks too small in Applejack’s flashback. He might not have reach puberty yet. I feel no regret on saying that.
 
So yeah, I made myself confused. :/