For four years, Sunset Shimmer has carried a torch for Miss Cheerilee, and for four years, she's struggled to look at her without thinking of the one who got away.
When Sunset Shimmer gets a letter from a not-so-secret admirer, she thinks it's just a bump in the road. She doesn't know it's all about to end. But Cheerilee knows. She's always known.
After Anon's arrival in Equestria, it was decided that Ms. Cheerilee would act as his guide and teacher while he gets adjusted to his new life. Neither of them are happy about it.
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.
Off Creem and Suction. Cherilee is the Teacher at the Latex Elementary Boarding School. School is fun, when you choose the school and have your friends by your side. Besides, learning should be exciting enough to keep you tied to your desk.
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.
(Takes place after "Hard To Say Anything".) Cheerilee is crushed to hear that Big Macintosh has found a new special somepony, but convinces herself it's for the best. That is, until Big Mac meets with her to share an important confession.
Cheerliee has always looked out for Pinkie Pie. Hooves always looks after Bertie Whickers. But when Pinkie met Bertie, something happened that neither the schoolteacher nor the butler had looked for.
Eight years since Bookends Part 3: Or Family Values. A normal life in Equestria is threatened. After all this time and with foals to protect, are the Main 6 up to the task once more?
When Cheerilee catches wind of Big Mac and Marble Pie's fling over Hearth's Warming, she begins to question what her friendship with Big Mac really meant. Was there ever something more to their relationship?