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“Like, can you even braid a friendship bracelet?”
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IDE\Theory: that “80’s Cheerilee” picture was faked, and not really made in the Eighties. She actually grew up as one of these lesbian androgynous emo-teens with all the dyed hair and the snake bites piercings and the all.
If we take the “Call of the Cutie” literally and believe Cheerilee got her cutie mark in the mid-Eighties while the present day ponies are living in the time period when the episodes air, she would be much older than Rarity. On the other hand, one of the background ponies in “Cutie Mark Chronicles” looks like Cheerilee. So who knows.