Chrysalis is dealing with some... unique magical problems. Cherry Jubilee is dealing with some finacial and relationship problems. Diamond Tiara is dealing with having to be in the room with the two of them.
(Takes place within the universe of "The Sitter with the Diamond Tiara" and its semi-sequel "A Dazzling School Daze".) Plagued by uncertainty about her future, Diamond Tiara visits Cheerilee in hopes the teacher can guide her one last time.
After Diamond Tiara confronts her mother in the episode "Crusaders of the Lost Mark," she is gifted a set of wings and a horn. But her mother forces her to go to Boarding School, where she learns to face herself and find out who she wants to be.
Filthy Rich has always considered himself to be a good parent. But when Miss Cheerilee requests a meeting with him, he may have to face the fact that his darling daughter isn't as perfect as she seems.