This idea came to me in a dream and I just had to draw it as soon as possible.
To me Fluttershy’s eyes have always looked sad, like she’s constantly hiding something, burying a painful memory in the bottom of hear heart, always pretending everything is okay while her mind inevitably goes back to those tainted memories over and over again.
GREATEST HEADCANON: ACCEPTED.
It even plays into the headcanon that Fluttershy should be the one to teach Scoots how to fly (or, that she doesn’t even *need* to fly in order to be happy).