- Emily has to go back to town to go to school. It's heartwarming, but also a pretty sad moment for Little Bear, who probably doesn't know when he'll be able to see his best friend again. This is fortunately resolved in the second season, when she moves to the forest.
- All the Sick Episode/s (A Flu, Little Bear's Sweet Tooth, Pillow Hill)
- "Little Bear's Sweet Tooth" didn't even start out as a Sick Episode. It started off as a perfectly normal episode but when they end up with the pie Eating Contest, Little Bear starts groaning and not wanting to eat pies. That night at bedtime, his stomach still hurts and he claims he's lost his sweet tooth.
- In "Lucy's Okay", Little Bear, Duck, Owl, and Emily pretend that Lucy died and they're having a funeral. But the funeral is so convincing that Owl and Little Bear actually feel sad and nearly forget that they're just pretending, and Duck completely forgets and she seems to be the most emotional, even crying instead of saying her fake eulogy. To make matters worse, they told Mother Bear, Cat and Hen that Lucy was dead without giving them the heads-up that it's just a serious "game". Emily admits to Cat and Hen that they were pretending, but Mother Bear is still uninformed (although she likely is rational enough to know dolls can't really die). Luckily, the episode has a Happy Ending where they realize that, just as the title says, Lucy's OK.
Tearjerker / Little Bear