Caillou, Leo and Rosie are all outside playing when Clementine shows up wearing a red ribbon. She explains that it was for swimming and Leo shows off a blue one that he won for being the best runner at his Dad's office picnic. Caillou comments to himself that he wishes he could win a ribbon like Clementine's. Grandma notices this and so she goes inside to find some ribbons. She announces that she's hosting games. Rosie asks to join in too and everyone agrees. Grandma's first game is to walk heel-to-toe. Clementine wins this one. Then, Grandma holds a contest for the biggest smile. This time, Leo is the winner. Caillou starts to become a bit upset, because he really wants to win a ribbon. Mommy reminds him that games are supposed to be fun. Caillou thinks about this for a bit and agrees, deciding to take part in the next game. This time, Grandma asks everyone to do a silly walk. This time Rosie wins. In fact, Caillou declares her to be the winner, since her walk is obviously the silliest. Next, they have an obstacle course. Caillou imagines that he's in a real race with an announcer and a crowd. He doesn't win this one either because, Gilbert gets in Caillou's way before he can finish, so Leo wins instead. Caillou is still really having fun. Grandma has one last game. This one is a no smiling contest. The objective is to not smile or laugh or at all, no matter what sort of funny things Grandma does. Rosie is immediately out, but Grandma has her join in trying to amuse the others. Grandma and Rosie do raspberries. Clementine is out next and she joins them. They pretend they're chickens and Leo is out. Caillou wins and finally gets a ribbon. Gilbert gets a ribbon too for having the best purr.
- Rosie is seen smiling before Caillou sighs during the no smiling contest.
- Boris is mysterious absent in this episode (He is not see or mentioned).