When Cheese accidentally begins writing her new fantasy novel inside Boy's diary, Boy is inspired to live out the life of the novel's great hero! By applying the story to his life, Boy is soon one of the cool kids, making Girl jealous. When she sees Cheese's novel-writing is the cause, Girl helps her write the next chapter to take Boy down a peg or two.

The family is going on a canoe trip, and Boy and Girl are each allowed to bring a friend. For Girl, the choice is easy - she invites her BFF. But Boy realizes he doesn't really have any friends outside his own family. The rest of the siblings set out to help Boy find a friend for the canoe trip - but can he overcome his shyness?