After her sand castle is washed away by the ocean, Dinky Hooves takes it upon herself to do something that should have been done centuries ago: destroy the moon.
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.
After going to Coloratura's concert, Sunset gets both good news and bad news. Somepony stole her identity and is running around with her face. That's the good news.
Rarity figures out that Cheerilee has a crush on Twilight, and that Twilight is oblivious. Rarity decide to play matchmaker. And Blue Bonnet is the worst delivery pony. Nothing can posi-blie go wrong.
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.
When Twilight accepts Cheerilee's request for her to substitute teach, she quickly realizes the topic is "the birds and the bees". So, not wanting to let down her students, Twilight attempts to teach the subject to the best of her ability.
Cheerilee is perfectly happy being an earth pony and not being able to find better employment beyond Ponyville Elementary, or so she claims. But when she suddenly isn't an earth pony anymore, her life gets all kinds of crazy.