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Description

Cheerilee’s cute in a cheerleader outfit, yet I can’t help but feel she’s… a bit out of place.

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why
I know what you mean op. The first filly pops up and you go: “Cute!” Then the colt: “Adorable!” And finally, Cheerilee: “I should not be feeling this way around children!”
 
There’s a tone shift when you go from child in cute outfit to adult in cute outfit, I feel. It doesn’t help that there’s a short skirt involved.
Entrinity
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).

I could never date a kindergarten teacher, or anyone who teaches lower than 3rd grade for that matter. I feel as if they’d be either really childish to the point of being unbearable(and that’s saying something to me) or they’d be really controlling and talk down to people…. but I could date Cheerilee!