On a perfectly ordinary day in Equestria, school teacher Cheerilee notices something... a lot of things wrong with one of her students. She and her boyfriend Big Macintosh set out to investigate and end up taking a trip through time and space.
The Apple family farm is in trouble, and Big Mac has only one day to get three hundred and fifty bits together. He’s only got one chance. It’s just a roll in the hay— it doesn’t mean anything…
Cheerilee is sent to investigate a mysterious outbreak of love sickness on Hearts and Hooves Day, but ends up getting much more than she bargained for.
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?
With Cheerliee acting as his pretend teacher for the day, Macintosh is roped into playing a number of childish games at school involving silly tests, arts, and diapers.
Cheerilee had a accident. A deadly accident. She is not going to make it. Luckily, there is somepony to look out for her... someone she cares a lot....
Big Mac has struggled with illiteracy his entire life, until he finally gets the courage to ask Miss Cherilee to teach him. What he didn't realize was, that along with reading came happiness in ways he never imagined. CherileeXBigMac
Not long after Fluttershy sat in for me with the Ponytones, Rarity asks me out to a fancy dinner. How do I learn to speak up and tell her that I'm only interested in Cheerilee?
A holiday tale in which Cheerilee learns the true meaning of the word "wassail"; Granny Smith fails to learn the true meaning of the word "polymath"; and somehow, amidst it all, three flowers finally begin to put down roots.
(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.