Rainbow Rocks 10th Anniversary - Let's celebrate the 10th anniversary of Rainbow Rocks with an art event! Here
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safe2233038 artist:andy price3774 idw21654 braeburn7080 bumblesweet154 caramel2991 cheerilee11446 goldengrape825 lyra heartstrings34846 meadow song771 minuette7099 moondancer6265 princess cadance41343 shining armor28878 sir colton vines iii825 soarin'18151 sugar grape74 sweetcream scoops217 thunderlane5029 wheat grass153 alicorn327955 earth pony529936 pegasus522201 pony1663171 unicorn565820 g42095032 neigh anything196 80s1307 80s cheerilee426 apple family member3685 background pony12569 boots35324 born in the usa1 bow47259 braces1934 bruce springsteen7 canterlot academy4 comic138727 comic cover1233 compact cassette114 cover3967 ear clip19 fall formal255 female1870627 hair bow27276 kiss (band)47 leg warmers3947 male573008 men without hats11 necktie12291 new coke3 new wave11 ponified52784 quarterflash6 quarterhorse6 raised hoof74073 shoes63157 soda2129 springsteed1 stallions without hats2 star wars3898 star wars: return of the jedi65 sunglasses21922 tail bow9986 tape2623 teen princess cadance1185 teenage shining armor103 teenager8027 yearbook120 younger23719

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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 -
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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. :/