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In these skits, Herry Monster goes to visit a real kid at a day care center, talks to the kid, and then goes to his own day care, where he tells various monsters (including Kermit the Forg and the Two-Headed Monster) what he learned.
During the seasons this segment was run, the monsters featured in the segment would appear in other parts of the show, with consistent performers for each one, including Joey Mazzarino (purple), Stephanie D'Abruzzo (green), Jim Martin (yellow) and Alice Dinnean (Kermit the Forg).
|Picture||Theme / First Apperance||Description|
| Isty Bitsy Spider|
|Sam, Emma and Stephanie teach Herry to sing "The Itsy Bitsy Spider". The monsters sing it at Monster Day Care.|
| I'm a Little Teapot|
|Herry asks Eugene and Karin to sing "I'm a Little Teapot."Then he goes to Monster Day Care, and demonstrates his new skill.|
| The Letter M|
|Nicole shows Herry Monster the letter M. Later on, he and the daycare monsters make a letter M of their own, sing "M-M-M Monster Meal," and eat their M.|
| Nap Time|
|Herry witnesses a group of kids taking a nap, and does the same with his monster pals later.|
| Cubby Holes|
|Herry Monster talks to kids about putting things away in their cubby holes. Back at Monster Day Care, Herry tells the monster gang about what he learned.|