Jamie realizes that middle school is more than crazy as her love life becomes of triangle of crushes, someone gross is attracted to her, she is crushing on Hudson, and he only has eyes for "the Prettiest Girl in the World.".
As their school gets ready for the annual Fun Fair, Jamie and Isabella agree to compete in the bottle toss game and to terrible consequences for the loser.
Jamie begins to wonder if adults lose their sense of humor when they get older after noticing that her social studies teacher, Mr. VanDoy, never smiles.
Jamie Kelly has an eventful month and writes about it in journal form, discussing the arrival of a litter of puppies and the latest gossip about her friends.
Jamie Kelly shares with her diary her excitement about the fact that students from Wodehouse Middle School will be going to Mackerel Middle School temporarily.
