Question: Do you reread a lot? Why (not)? Name a book you have reread many times.
I reread all the time. There are many, many books that I have read more times than I can count. Lately, I've been on a roll with reading new books instead of rereading, and I have so many new books I want to read that that looks far more tempting to me right now. However, the truth of the matter is that I get far more out of a book I read more than once. If I liked it, chances are good I will be reading that book again. If I don't reread a book, it usually means I didn't like it and considered it unworthy of my time. There are books that I initially couldn't get through that I went back and read happily, notably Stephen Hawking's The Theory of Everything, Madeleine L'Engle's A Circle of Quiet , and even Tolkien's The Hobbit.
I think the book that I have read the most is probably A Tangled Web by L.M. Montgomery. There is something about this book that never ceases to interest me, it has a very large and varied cast of characters and each one of their lives and especially the intersections in their lives resonates deeply with me. I haven't quite dug to the root of my interest, but I suspect it has something to do with a personal interest in a large and complicated extended family. The matriarch of the clan, Aunt Becky, is somewhat reminiscent of my own Nana.
I have also reread all of the Harry Potter books, Lord of the Rings books, and the Sisterhood of the Traveling Pants books numerous times. I suppose series leave more scope for characters and plots to develop and it's pleasing to remind myself again of the intricacies involved and make new observations.