(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 meeting Diamond Tiara for the first time in several years, Applebloom is filled with complicated feelings about her sexuality, and what it truly means to forgive.
(Semi-related to "The Sitter with the Diamond Tiara".) Lil' Cheese is worried about having a new teacher, despite the reassurances of his parents. Luckily, his new teacher knows just how to dispel such worries.
After many hurdles and pitfalls along the way, a very special day has finally arrived for Diamond Tiara. It wouldn't be complete though, without an unwelcome appearance from a certain someone, who might be about to make her an offer she can't refuse.
When both Pinkie Pie and Cheese Sandwich are called out of town for separate but important occasions, they rush to find a suitable foalsitter for Lil' Cheese. An unlikely pony volunteers for the job, Diamond Tiara.