Headcanon: During her childhood years, Fluttershy could never win at anything, and she was okay with that. It wasn't until adulthood that she won something. At that time, she didn't even know how to react, really. Later during Friendship School, she would drop subtle hints about her past, and it didn't take long for the students to put two and two together. That's why she always wins Teacher of the Month.
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