The book starts as a regular novel, where we met Jerusha Abbot (she hates her name and makes everybody call her Judy), an 18 year old orphan girl. At her orphanage kids would leave around age 16, but she was allowed to stay for 2 more years while she attended to high school and helped with the younger orphans. She had a very good academic development and great writing skills. These achievements induced one of the orphanage’s Trustees to pay for her college education. The only requirements: he wanted to stay anonymous and Judy must write to him about her studies, without expecting or demanding any answer from him. From this point on, the novel turns into an epistolary one, where we read every letter Judy wrote to the Trustee (whom she named “Daddy-Long-Legs”, because all she saw of him was a very long and slender shadow). Judy’s writing is hilarious and sharp, as she gains trust in her benefactor. She writes to him as she would write in a personal diary, so we get to know not only her college routine, but also her friends, her insecurities regarding her backstory and the differences she perceived she had with the other girls, who had the privilege of growing in a loving family, and any kind of adventure and misadventures she gets into.
I read this book for the first time when I was about 10 years old, and re-read it uncountable times. I believe it was my first approach to letter writing and the reason I always wanted to keep correspondence. The book is now on public domain, so you should be able to read it online or download it for free. I highly recommend you to get a copy that includes pictures, because Judy not only wrote her letters, she added drawings too!