It's been ten years since Twilight had met Cadence that chilly October day. Now a young teenager, she's looking to reconnect with her old sitter in hopes that she can get Shining and Cadence together again. But like always, some things are easier said than done.
Cadence has a crush on Shining Armour. Not only that, but she needs some extra cash. What better way to earn money and get close to her crush than watching his kid sister?
A now seventeen year old Twilight Sparkle with the help of her friends, tries to reconnect her brother with his high-school sweetheart and her old babysitter, Cadence.