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You know what’s so wonderful about the term “annual”?
 
It means “once a year”.

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@mugg
 
Cartoon logic. Bart Simpson should be nearly 40 by now but nobody would argue that a single year has gone by in Springfield.
 
Too many events contradict the one-year idea. Besides, in television, it’s long been the accepted norm that one season = one year.
mugg
The End wasn't The End - Found a new home after the great exodus of 2012

Btw, as a matter of fact, I’ve been working on a very detailed timeline. I’ve rewatched all episodes and have looked up the “timeline” tag here (so I came across this discussion). I’d like to post it when it’s finished later.
mugg
The End wasn't The End - Found a new home after the great exodus of 2012

We can safely assume Ep166 is one year because Celestia says “the Summersun Celebration has always been a terrible reminder that she had to banish her own sister but now it is to celebrate her return”. It is not really confirmed but it is implied that one year passed. Also the CMC didn’t age (they probably never will but I’m just saying, 812 year olds becoming 3 years older should be noticeable in their appearance).
Prof.NightJack
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Gizmonics Scientist
Considering the passing of days is a controlled phenomenon on pony!Earth, maybe their years aren’t the same as our years. Maybe they’re in a base-10.
 
That is a good point and interesting idea.
OverlordScorpion
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Λάθε βιώσας
You know what’s so wonderful about the term “fiction”?
It means “we don’t have to sit through every single moment of boring daily minutiae of every character’s life all the time every time and can in fact skip over all sorts of current events that either don’t involve them or aren’t important to their stories”.
 
Oh, we do too. Its obsession with details what made this fanbase come to existence.
 
Do you mean to imply, OP, that everything we’ve seen in the series so far has happened in the span of roughly 36 hours in-universe?
 
Why not? It’s called decompression, and its a resource just as liked as it is hated.
 
There are over one hundred scrolls in that pile.
 
Considering the passing of days is a controlled phenomenon on pony!Earth, maybe their years aren’t the same as our years. Maybe they’re in a base-10.
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You know what’s so wonderful about the term “fiction”?
 
It means “we don’t have to sit through every single moment of boring daily minutiae of every character’s life all the time every time and can in fact skip over all sorts of current events that either don’t involve them or aren’t important to their stories”.
 
Do you mean to imply, OP, that everything we’ve seen in the series so far has happened in the span of roughly 36 hours in-universe? If not, then you’re allowing for the fact that OH MAH GAWD THINGS HAPPEN OFFSCREEN, in which case your argument is dead on arrival. I’m pretty sure Pinkie Pie doin’ the P.P. Dance outside an outhouse in Dodge Junction wasn’t the only time anyone in the entire FIM universe has ever used the restroom; chances are, other things have happened offscreen as well.
 
@Conan Royal  
proooooof
 
Celestia did not in fact explicitly state that the current Summer Sun Celebration was the next one after that of the Series Premiere, only that it was no longer a celebration of the defeat of Nightmare Moon. All it takes to add at least one more in is assuming that Luna wasn’t up to resuming her role as an active princess yet, and the fact that she was markedly different between her S1 and S2 appearances means that her resumption of the role was not an immediate thing.
 
Twilight, however, was extremely specific in Lesson Zero that she had to write a Friendship Report “EVERY. SINGLE. WEEK!” Here she was in the previous episode, when Celestia returned all of those reports all at once.  
full  
There are over one hundred scrolls in that pile.
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@Prof.NightJack  
I feel similarly, it’s very difficult to gauge exactly how much time has passed.
 
A lot of things can also happen off screen that we’re not aware of, as others here have pointed out.
Prof.NightJack
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The End wasn't The End - Found a new home after the great exodus of 2012

Gizmonics Scientist
Personally, unless the amount of time that passes is relevant to the plot I really count care less about hoe long it has been.  
Blame the Pokemon anime, back when I was a fan I was always trying to understand the time scale, and Power Rangers, until Linkara said his ideas of the PR universe having different properties of physics and stuff it gave me a headache on why they set SPD 20 years after the year it was when airing but 1000 yeas in the future in Time Force.
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What does it mean?!?
@martianmister  
Yeah most likely, I mean there is a small chance that they could be the same winter, since there is no letter written in Hearth’s Warming Eve, so it could be before lesson zero. Alternatively winter wrap up could be after Lesson Zero, since twilight is the one that learns a lesson that episode, so she doesn’t write a letter for anypony else, but I also highly doubt that.
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What does it mean?!?
There’s no way a season 2 episode takes place after an season 1.
 
I think you meant that the other way around, but even then, any episode that is centered on Twilight from season 1 could technically take place after Lesson Zero. Only the episodes where Twilight learns her friendship lessons indirectly have to take place before Lesson Zero.
 
 
I would still have to say that it is impossible for the first episode of season 4 to be only 1 year after the pilot. Firstly there is at least one episode that takes place during spring that takes place before Lesson Zero, namely Party Of One. (Here’s a chart explaining the chronology of season 1, you’ll find the explanation as to why Party Of One takes place during spring >>337733 (merged))  
Since Party Of One takes place during spring, that puts Lesson Zero somewhere around spring at earliest, summer or fall at latest, so for the benefit of the doubt let’s put it as early as possible so that it doesn’t break the opener of season 4. That task will be done by Super Speedy Cider Squeezy 6000.
 
SSCS6K takes place during cider season, i.e. around the same time of year as Applebuck Season, since the apples are being harvested. So probably late summer or fall. Since Applebuck Season takes place after the pilot, and therefore after the summer sun celebration, it means that the same must apply to SSCS6K. And that is why season 4 can’t be just 1 year after season 1.
Background Pony #AEE1
@nf  
I’m not sure why people seem to assume that just because two events are depicted, those are the ONLY times those events have taken place, and therefore must be exactly X time apart.
I don’t have Christmas photos from every year. Does that mean the intervening Christmas’ never occurred? No.
 
Agreed. The refusal to consider that things happen outside what is shown to the audience is annoying and seems to be the main cause of confusion with respect to time passing on the show. Rainbow saying it’s her first winter with Tank is the only concrete evidence we have for how much time has passed in the show. Every other potential thing brought up (the Summer Sun Celebration, the galas) has been speculation.