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safe2150990 screencap293353 applejack198567 derpy hooves56989 granny smith6069 pegasus486485 pony1578822 g42004247 where the apple lies582 background pony12214 bandage7525 double mane77 female1777372 hospital1827 mare726353 teenage applejack325 teenage derpy hooves15 unnamed character4764 unnamed pony2865

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Japanese Teeth
Non-Fungible Trixie -
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The End wasn't The End - Found a new home after the great exodus of 2012

Clock. Is. Ticking.
So, now that Parental Glideance has come out, this raises some interesting questions. In that episode, a flashback shows that Derpy was apparently a pretty good flier and actually managed to outfly RD and some of the other Wonderbolts as a filly. What’s interesting is that at first her eyes are normal and worsen as time goes on, and she starts to place worse and worse in the races:  

 
Combining that with this, it looks like Derpy was a promising flier whose eye problems were hindering her performance, prompting an unsuccessful attempt at fixing the problem surgically.
Background Pony #AA2E
I wonder if Derpy was blind at birth or something? And that Equestrian Medical Science had evolved enough to cure blindness?
 
It would explain why she can make her eyes look in different directions all the time. She never used them till later in her life, and now she uses them ambidextrously.
 
Of course, I’m trying to look at the silver lining this scene is showing. She had eye surgery earlier in her life, but it (probably) didn’t have anything to do with her cross-eyed look.
Background Pony #6BB4
@SeraphimDawn  
Just because her eyes are crossed in present time doesn’t mean it failed. I have strabismus, I corrected my eyes when I was little. My got crosseyed again much later, probably because I didn’t use my glasses enough (I quit using them after people kept making fun of me). I’m considering having a second surgery because now people make fun of me for my strabismus. I wish I knew people expect from me? They bully me when I’m crosseyed, but when I have surgery and use glasses to prevent it from returning they bully me for the glasses. I wish they were like Bronies and just accepted me with the eyes I have. :(
Background Pony #41E2
@Daneasaur  
Nah, only one of the nurses eyes is half closes, the other (her left eye) is wide open, meaning she has a raised eyebrow here, not a sad double eyebrow.
Background Pony #AC70
@Vree  
I’d like to think she got her teenage growth spurt earlier than Applejack.It’s more easy for the timeline this way
Vree
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@Pagan  
She’s older than Jack here despite the pics you posted, so this is obviously Eternal Derpy the time traveller (the one who attended Twilight’s first sun festival)
Background Pony #897E
This really isn’t far fetched. I had surgery on my eyes as a kid due to strabismus. Can’t say it helped that much.
Background Pony #8F0D
derpy nnnnnnnnnnnooooooooooooooooooooooooooooooooo !!!! they fuck her eyes those bastards fuck her eyes !!!
Daneasaur
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Judging by the doc/nurse there, she’s undergone a procedure and it was not a success… OR she did something that hurt her eyes and the nurse is delivering the “bad news”.