Caillou learns to cope with change. It's raining outside but there is no stopping Caillou! He sees a robin catch a worm and is thrilled when he finds a worm of his own. When Leo calls to invite Caillou over to play, Caillou isn't sure at first if he wants to go since he's having such a great time by himself. Later, Caillou, Rosie and Mom are having fun at the park when the ice-cream man comes around. Caillou wants an ice-cream but the ice-cream man leaves before he can get there. On a suggestion from Dad, Caillou becomes the 'ice-cream man.' Also, Caillou just loves his Superbear storybook. When Caillou wants to hear it again and again, Dad explains that he has other things to do. Caillou decides to make up a story on his own and plays it out with Rosie. Then, Caillou is playing a board game with Mom and he gets a little upset when he discovers that she is going to win. He tries to change the rules but Mom stands her ground. These are the rules and you can't always win. Caillou is excited when Miss Martin takes him and his friends to the park for some special activities. All the rules are not easy to grasp, and the kids have a few comical mishaps in the process. Caillou discovers that you don't always have to win to be proud of yourself.