| 1 | !!This episode contains examples of the following tropes: |
| 2 | * AbnormalAmmo: During the pirate fantasy sequence, Christopher Robin, Pooh, and Piglet fire pillows from a cannon at Tigger's ship. |
| 3 | * AnAesop: Babysitting may be more trouble than what you think. |
| 4 | * BabysittingEpisode: In the first half of the episode, an unnamed babysitter takes care of Christopher Robin. In the latter half, Christopher Robin has to babysit Roo while Kanga goes out into the Hundred Acre Wood. |
| 5 | * BreakTheCutie: Kanga breaks down crying after failing to find Roo. |
| 6 | * DoesThisRemindYouOfAnything: Kanga breaks down crying over Roo going missing. But due to Roo being babysat by Tigger at the time of going missing, the double meaning hidden here is a metaphorical allegory to child abduction. |
| 7 | * TheFaceless: As with Christopher Robin's mother, the audience never sees the babysitter's face. |
| 8 | * FakeOutOpening: The opening scene where Christopher Robin rescues his friends from prison via train is actually his imagination. |
| 9 | * GoToSleepEnding: The episode ends with everyone going to sleep. |
| 10 | * HalfwayPlotSwitch: The first half of the episode involves Christopher Robin causing trouble for his babysitter while refusing to go to sleep. In the second half, Christopher Robin gets to exprience the babysitting himself. |
| 11 | * JustTrainWrong: During the FakeOutOpening when the train goes down a steep hill, Tigger has Piglet hit the brakes; the control he activates is the roof rope, which is what blows the whistle. |
| 12 | * LoopholeAbuse: As put by Tigger, the babysitter said "get into bed," but she didn't say "go to sleep." |
| 13 | * ParentalBonus: Kanga's adult fear over Roo going missing while being babysat by Tigger [[DoesThisRemindYouOfAnything bears resemblance to child abduction cases]]. |
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FollowingContext Recap / TheNewAdventuresOfWinnieThePoohS1E9BabysitterBlues
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