The Secret Diary of Adrian Mole, Aged 13 3/4 by Sue Townsend
Adrian Mole is a British teenager who records his life happenings in a diary. He writes about his mother's affair, his acne, bullies at school, and his crush on a girl at school. Funny, sad, and smart but also angsty as only teenage boys can be (and sometimes a bit gross). Although this book was written about 15 years ago, it's surprisingly timeless. I guess the angst of teenage boys is the same throughout the ages?