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Pony Driland fic!

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safe2263217 artist:andy price3811 idw22426 braeburn7181 bumblesweet154 caramel3028 cheerilee11545 goldengrape840 lyra heartstrings35199 meadow song788 minuette7210 moondancer6332 princess cadance42011 shining armor29296 sir colton vines iii840 soarin'18379 sugar grape74 sweetcream scoops218 thunderlane5116 wheat grass153 alicorn335033 earth pony544046 pegasus534543 pony1695370 unicorn579358 g42123471 neigh anything197 80s1330 80s cheerilee432 apple family member3769 background pony12681 boots36476 born in the usa1 bow48606 braces1990 bruce springsteen7 canterlot academy4 comic140190 comic cover1294 compact cassette118 cover4059 ear clip20 fall formal257 female1904292 hair bow28112 kiss (band)47 leg warmers4086 male584002 men without hats11 necktie12842 new coke3 new wave13 ponified53732 quarterflash6 quarterhorse6 raised hoof75879 shoes65057 soda2178 springsteed1 stallions without hats2 star wars3929 star wars: return of the jedi65 sunglasses22283 tail bow10405 tape2773 teen princess cadance1210 teenage shining armor107 teenager8328 yearbook122 younger24281

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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. :/