(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.
The small snippet of two tired souls in the midst of the happiest and loneliest time of the year, where perhaps a few too many sad stories pass by before their eyes.
A look inside the hidden perspectives of the average pony by your average joe. Starting with the imprisonment of Cozy Glow, this pony sets out to expose the hidden problems of Equestria that its residents have a right to know.
At the request of the EEA, Cheerilee takes a day off from teaching. In fact, it's her first day off in ages and that is a bit of a problem for the mare. Fortunately, there are some things she can do to keep herself busy.
(Takes place prior to "The Big Mac Question for obvious reasons.) Cheerilee arranges a meeting with Sugar Belle at the schoolhouse to discuss the subject of Big Macintosh. Specifically, Cheerilee wants to clear up a misconception Sugar Belle has.