- Rilakkuma and gang are shocked and left in tears in Episode 6, when Kaoru basically suggests that they go live with Tokio if they're dissatisfied with her obsessing over her fortune instead of cooking for them. It's later implied that Kaoru thought they'd stay with Tokio temporarily, except he can't accomodate them because his mother is allergic to fur, so they end up wandering around outside instead. Luckily, the gang fish to amuse themselves in the meantime.
- In episode 8, Rilakkuma, Korilakkuma, and Kiiroitori all get jobs to help support Kaoru after her spending fiasco and losing 10% of her winter bonus. Everyone does spectacularly at their jobs except for Rilakkuma, who keeps getting fired. The big guy starts tearing up at his last job, and he gets frustrated when he can't even do something as simple as picking fruit from a tree. He offers himself for Kaoru to eat as his last resort.
- In episode 9, Rilakkuma gets sick after catching a cold. That night, he has a dream where he dances with the snowmen Korilakkuma and Kiiroitori built, but the next morning, he finds out they've all melted and weeps over the loss of his friends.
- Tokio moves away at the end of the series. Both Tokio and the critters tear up as they say their goodbyes, with the latter chasing after the moving truck as it drives away.
- Kaoru and friends move out of her apartment at the end of the series due to her apartment building being demolished. In the final shot, you can see her apartment room, which she had spent a whole year making memories, completely empty and barren.
Tear Jerker / Rilakkuma and Kaoru