Are You There God, It's Me Margaret? was mine. 4th grade.
First book you read that had any depth?
My mom read A Tree Grows in Brooklyn to my sister and me when I was quite young; I don't remember being able to read myself at that point. She also read Little Women to us but I don't consider it to be particularly deep. I can't remember the first book that I read that had depth. Maybe 1984 when I was in jr high although I remember reading books like A Wind in the Door and Under the Haystack earlier than that and they had depth to me when I read them. I don't know if they would be considered to have depth now. Maybe I am over analyzing this.
I remember liking the first chapter of Walden. I didn't realize when I started that not only was it something like 60 pages, but it was sixty pages, meaning not only did it start with page 1, but each page was a chore. Especially when you're taking notes. I think by about page 9 or 10 I decided hey might as well put in some effort and enjoy it, right?
I don't really think of books as deep and meaningful, I read books for entertainment. I think the first reading that really affected me was when I started reading the A section of the Washington Post every day in high school. I don't think I read a book that really affected me until I read the Old Testament in my 30s.
This is so off topic, but I don't mind if you throw in chess books or jokes.
Which book do you remember being the first which had any meaning or depth for you? How did it affect you?