Rarity was supposed to babysit tonight, but she got a ticket to a young designer's gala and asks Pinkie to take over. Pinkie agrees and takes the sitee, Lily Pad, into her home. An enthusiastic Pinkie asks what fun activity she wants to do, but Lily, who brought an electronic device with her, just wants to sit and read. As Pinkie grows increasingly bored, she has an idea. She asks Lily what the story she's reading is about, and begins to act it out with props and costumes as Lily describes it. While Lily is entertained, Pinkie has tired herself out, so Lily offers to read the story to her. The story lulls Pinkie to sleep as she mumbles that Lily will make a terrific babysitter one day; Lily replies she hopes she's as good as Pinkie.
- Bread, Eggs, Breaded Eggs: Pinkie's activity suggestions are: bake a cake, make silly hats, or bake a cake shaped like a silly hat.
- Canon Foreigner: Lily Pad has no known Equestrian counterpart.
- Captain Morgan Pose: Pinkie Pie dresses like a pirate and takes this pose, with a foot upon the sea decor she'd just set up.
- Changing Clothes Is a Free Action: As usual for Pinkie Pie. She's in top form in this episode and changes costumes several times in a flash.
- Continuity Nod: At the beginning, Rarity is wearing the dress she wore to the Crystal Gala in Legend of Everfree.
- Cute Bookworm: Lily is a small and endearing child who likes to sit quietly and read.
- Fun with Homophones: When Lily mentions the pirates in her story end up on a desert island, Pinkie brings two enormous cakes to figure the "desserts island".
- Manchild: Pinkie Pie, of course. This is the main joke that she lampshades; Lily is more babysitting her than she's babysitting Lily.
- Punny Title: The main joke behind the short is that it isn't really clear who's babysitting who, and the title plays into that.
- Reality Ensues: Not knowing who Pinkie Pie is, Lily is weirded out by her and would initially prefer to spend the night curled up on the sofa reading on her device.
- Showgirl Skirt: The very fancy dress Rarity is wearing to go to the "Young Designers Gala" is open in the front to emphasize her legs.