A new school year begins in Ponyville, and three new students enroll; an Earth colt named First Base, and two Pegasi colt brothers named Boomer and Butterscotch. Diamond Tiara falls for Boomer leaving Silver Spoon in the shadow, Dinky Doo gains a friend (and crush) in First Base, and Fictionary opts to make Butterscotch feel confident in himself.

However, when the Cutie Mark Crusaders are enlisted to help Dinky to fall in love with First Base and help Silver Spoon in splitting up Diamond Tiara and Boomer, one big mistake leads to potentially disastrous consequences for both sides. To make matters worse, all is not what it seems when Fluttershy reveals a dark secret. What secret is Fluttershy keeping from her friends, is Boomer really the honest colt Diamond Tiara sees in him, and why is Butterscotch so afraid?

Rated T for some death themes.