@LuminoZero  
the thing is he’s small and he doesn’t have a cutie mark. so he probably is younger, along with propeller head. either that or the cmc got their cutie marks right on time and not way after everyone in their age group.

My theory is that it’s one of those classrooms that has multiple grades, and the reason that Pip and Button weren’t around before is because they’re both a year younger than the CMC and weren’t in that class yet.
 
-Ridley

@redweasel
 
…Or maybe PIPSQUEAK is just very short for his age?
 
Nahhhhh.
 
-Lumino

5 years is a long time to be a young child  
…except when you only get to exist for 20 minutes a week  
…with long periods of hiatus, resulting in a total time of 20*(3*26+13+18) or 36 hours and 20 minutes, assuming off-screen time still counts for you.
 
even if I was just doing highlights of my life, 36 hours wouldn’t even catch a year of it. these marks were earned because of exhaustion of the patience of the show creators, not the patience of the characters. they’re not even the last in their class to earn their marks, though pipsqueak must be some kind of 5yo prodigy to be in their class, considering how big he is.

@Ridley Wolf  
That sentence started well.

@Ridley Wolf
 

 
-Lumino

@Brony_Conundrum  
The mistake that most people make is in assuming that the MLP:FiM timeline is a linear progression of sequential events, but actually from a non-linear, non-subjective viewpoint it’s more like a big ball of wibbly wobbly timey wimey stuff.

I thought the general consensus by now was that the FiM timeline makes no bloody sense at all, and trying to make sense of it will only give you a headache.

@Psycho Shy  
It’s been established that the timeline of the first few seasons was out of order.
 
We only got real confirmation of a timeline in the first episode of S4, when they celebrated the first Summer Sun Festival since Luna’s return. That implies that the events of S1-S3 took place in a time span of less than a year.

@LuminoZero
 
If my years of Dark Soulsing have taught me anything, it’s that if all you are given is straws, you make those straws into something beautiful.
 

 
 
I’d like to believe that as well, but…  

@Lupin Quill
 
Is the crux of your second paragraph REALLY based on Discord making sense and not singing songs out of season?
 
Also, moons is an archaic way of saying month. Since there is one full moon per month, roughly.
 
-Lumino

@PonyPon  
It’s unlikely.  
However;  
Let’s remember that we’ve also had at least two instances of winter. Once whenever the first Hearth’s warming and winter wrap up were depicted, and the other this season with Tank hibernating.
 
What do we get roughly in the middle? Discord humming the Winter Wrap up song in his bathtub in the s4 opening. Now, I know that he’s chaotic an’ all, and even Pinkie had her “Fruit bat round up, fruit bat round up!” moment, but we can’t overlook any evidence. I don’t know about you, but I don’t burst out singing (Which I do a lot) Christmas songs in the middle of summer (which is pretty much taboo).
 
We’ll I wouldn’t be the the first to point out that time is convoluted in Equestria, either. It’s an awkward and trying matter. Especially now that Equestria has this measurement of time called “moons” which supposedly have no human equivalent.

@Psycho Shy  
That’s what I always figured, that she meant that one.

@LuminoZero  
Once in “The Best Night Ever.”  
It was mentioned to be coming up soon in “Sweet and Elite.”  
And once in “Make New Friends but Keep Discord.” And if Twilight meant to refer to this gala with the previous one, I’d be sincerely surprised.

@Background Pony #3D84  
You’re probably thinking of the time Twilight needed to become a princess - like I did before reading all the comments - because yeah, two Gala’s so far

@Psycho Shy
 
3 times? I only remember twice.
 
-Lumino

@Background Pony #3D84  
The Grand Galloping Gala has passed at least three times; if we assume it’s an annual event, I’d easily say it’s been a little over three years.

And it was so worth it.

Halo wars?! I was a expecting a Star Trek thing, but DAMN is that an obscure reference. Even the tags agree that that’s an obscure reference.

Even though it’s been generally accepted that’s only been about a year in universe