S5·E47 It's Not Too Big for Me!

Caillou is keen to go sledding on the Big Hill... until he stands at the top of the hill and realizes it really IS BIG. Daddy senses Caillou is afraid to admit hes not ready for the big hill, and gives Caillou an easy out - by saying Rosie needs someone to play with on the little hill. Later, when Andre decides to sled down the big hill but he too is afraid Caillou helps his friend save face by inviting him to sled on the little hill with him and Rosie.