So Cheerilee is a full grown mare here. She was in the same class as Rarity in the cutiemark flashback episode, which means they are both the same age. Which also means Rarity and Fluttershy are the oldest among the mane 6 as Fluttershy had a teenage body in the flashback episode indicating she’s the oldest of the 6. The more you know.
 
I do wonder if Rarity’s mane still retained its curls in this time period or if she had zany hairstyles like Cheerilee here lol.

Hahaha nice callback!

@mjangelvortex  
I know.

@Meanlucario  
Understatement of the year.

@mjangelvortex  
Some Anons have issues.

@Background Pony #801D  

Still don’t get why he’s looking at Cheerilee when he already has his sister
 

Rarity Born 1970-1971  
Applejack born 1973-1974  
Apple bloom born 1988  
Spike born 1986

They look mischievous. Purrfect!~

ENEMY CRUISER SUNK!

@Sien69  
Gawd, Rarity is older than Applejack by a few years! Ship ruined!

So their age ranks like this:
 
Cheerilee=Rarity>AJ  
Fluttershy>Pinkie

@Meanlucario
 
Well, Cheerilee and Rarity seem to be the same age, as seen on The Cutie Mark Chronicles…

@Fluidty  
What makes you say that?

So, does this mean Rarity really is the oldest of the group (or at least older than AJ)? ‘-’

That’s looks like Dinky’s real mother.

Cheerliee was pretty hot back then.

@Background Pony #D00E  
then they must really be fans of TwiShy
 

@Background Pony #D00E
 
I think you’re really reaching with the retcon, and way off base with the “love poison was a good thing” bit.
 
This glance doesn’t mean they support CheeriMac. At best, they acknowledge it exists and threw this in for fun. It can also be read that Mac was just glad to see Cheerilee out with a friend.

@Beau Skunky  
@Masque Raccoon  
@cheezedoodle  
It’s true that this, in itself, isn’t a retcon of H&HD, but it’s obvious by now that DHX, or at least certain people there, support Cheerimac shipping. But going by H&HD, the two of them wouldn’t have started a relationship (or at least not done so for some undetermined period of time) if not for the CMCs. Therefore, either H&HD has to be retconned, or they’re saying the CMC’s use of the “love poison” ended up being a good thing after all (which, admittedly, is also possible).
 
@Masque Raccoon  
I’d like to headcanon this, and maybe I can, but it’s obviously not what DHX is intending.

I give Applejack the age of 12

@Mildgyth  
yes