In the first pages of the book, we learn of Erin Gruwell's shock that her high-school students have never heard of the Holocaust. She assigns them to read The Diary of Anne Frank. She wants them to understand that the segregation of minority students that is still occurring at the high school because of its various program tracks is similar to the way Jews were segregated in Nazi Germany and its conquered nations.

Miep Gies, who was still alive in the 1990s, was an employee of Anne Frank's father, Otto Frank. She helped hide the family at great risk to herself in the annex over the Franks' business during the Nazi occupation of the Netherlands during World War II. She also helped save Anne Frank's diary pages after the young woman was taken to a Nazi concentration camp.

Erin Gruwell's students were able to raise the money for a plane ticket so that Gies could come to Woodrow Wilson high School and speak to them. This visit was inspiring to the students and part of Gruwell's effort to ensure that her students' literary education was relevant to their lives. With Anne Frank's and others' diaries as models, the students were able to speak their own truths through diary entries and insert themselves into a literary tradition of writers opposing oppression.