@cheezedoodle
 
Agreed. I think it’s a nod to continuity (they’ve obviously known each other for a long time) and something to make the CheeriMac fans happy, without making it an actual thing in-universe.
 
Personally, I like the idea that they had a teenage crush going on, but developed into really good friends when they figured out it wouldn’t work. And still tease each other from time to time (Cheerilee’s fake “swoon” when Big Mac was singing).

If anything, this is a cute nod to cheerimac fans. Maybe he had a crush on her for years but never mustered the bravery to talk to her until that whole love poison fiasco.

@Background Pony #D00E  

 
That’s a very odd take on this scene.

@Background Pony #D00E  
I don’t see it as a retcon honestly, especially ’cause this is a flashback.

We get it, DHX, you want to retcon “Hearts and Hooves Day” out of existence; most of the fandom would cheer you on for doing so, so what’s stopping you?

@Background Pony #801D
 
You have a fucked up understanding of what love is.

@Background Pony #801D  
not really, no.

@Ryodraco  
yes it does

@Masque Raccoon  
Not to mention “considering someone attractive” doesn’t equal “being in love with/wanting to date.”

“That’s how everypony was wearing their mane back then.”  
Yet, we only see one.

age in this show make no sense

@Background Pony #D61D  

 
They made it very clear that they just prefer being friends. Not a matter of “lost interest,” but that they don’t see each other that way.

@Ryodraco  
We can actually at least estimate how old AJ is during this by the way, we know that Applebloom was 9 years old in her first appearance due to a test/audition script IIRC. And that a year has gone by at least since then (likely it’s been more now but let’s just go with that) that would make her currently 10ish now. So I would guess this puts AJ at about 12-15 in this flashback. Likely on the higher end of that age IMO.
 
Also given that, you can accurately guess her age now as well; a maximum of 9 years had to have passed between this and the start of the show making her 21-26 at the start of the show, or 22-27 now.

big mac could have cheerilee anytime he wanted  
guess he lost interest in her over the years

He’s thinking, “Eeyup, she’s still limpin’.”

Big Mac loves the leg warmers.

@Ryodraco  
That makes sense, considering the only times we’ve actually seen teen ponies like that are this ep and Fluttershy in Cutie Mark Chronicles, and we know that Fluttershy is only a year older than Pinkie, so the growth spurt probably happens pretty quickly.

@Spiritus Arcane  

 
More than that, Granny says all this happened when Applejack was only “a little older” than Applebloom, yet she physically looks very different. Perhaps the “gangly, long-legged” stage of a mare’s development goes by quite fast and they end up with a fairly mature body.

@Background Pony #3593  
Maybe Cheerilee just finished ‘filling out’ faster than the rest of her age group?

“That’s how everypony was wearing their mane back then,” eh, Cheerilee?

@gimmickfire5  
That he’s a teenager, and teen Cheerilee looks attractive to him for being a female?

Eyes on the prize.

@MadBrony  

 
Derpy appears to be the same age as Rarity too in The Cart before the Ponies, and Derpy here she has a teenager body like Applejack.  

Big Mac and Cheerilee are “just friends”. That look on his face suggests he was looking for more.

@Mildgyth  
I see. Thanks for letting me know.