(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 new bully strikes fear into everypony at Ponyville Schoolhouse, and her name is Dinky Doo! She's the baddest of the bad, and it falls to Cheerilee to set the filly straight before it's too late, at least according to Dinky herself.
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.
Applejack is usually upfront with her emotions. but when she develops feelings for Miss. Cheerilee she feels incredibly guilty. Luckily fate has given her a chance to work through it. Unfortunately, it's with the object of her affections.
After losing the stallion of her dreams Cheerilee had to wonder if there was ever a chance for happiness again? Little did she know another mare felt just like her.
(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.
One night, on Hearth's Warming, Diamond Tiara returned to her hometown of Ponyville. She'd hoped that some things might have changed. She didn't expect somepony to change so much.