Jamie Kelly writes in her diary about her social studies teacher, Mr. VanDoy, the budding relationship between her Aunt Carol and Assistant Principal Devon, and the real story behind Isabella's detention.

Jamie Kelly shares with her diary her search for inner beauty, dealing with fund raising, and problems in Phys ed class.

Jamie Kelly writes in her diary about her crush on Mr. Prince, the new student teacher at Mackerel Middle School, and she feels certain that he is the secret admirer who is sending her love poems.

Dear Dumb Diary Year Two is still laugh-out-loud funny -- but everything is another year dumber! As Jamie continues to grapple with middle school's Big Questions, she drops even more snarly gems of wisdom like, "Everybody knows that the more you love somebody, the less you try to look nice for them," and "People don't appreciate how much willpower it takes to do the wrong thing. (But Jamie STILL has no idea that anybody is reading her diary. So please,...

In her diary, middle school student Jamie Kelly describes her life at home and at school, including her attempts to triumph over her nemesis, the beautiful and popular Angeline.

While preparing for her aunt's marriage to her school's assistant principal, Jamie Kelly still manages to document in her diary all of the stupid things her archrival Angelina does, which is most relevant because they will soon be cousins.

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 is upset because she is now automatic friends with her old enemy Angeline, and so she tries to find something that she and her real friend, Isabella, can do together for the school talent show without Angeline.