In my honest opinion, life is too short to re-read a book that you have already plowed through and disliked. That would be like dumping a boyfriend and then considering to hook up with him again five years later because you think you may have been wrong. As a reader, my time is valuable and I have been reading books long enough to trust my instincts. I get what people are saying here about maturing and learning to read books through new eyes, but at the rate at which books are being published there are just too many good ones hitting to shelves to waste time on the bad ones.
William Faulkner's book, The Sound and the Fury, is definitely one and F. Scott Fitzgerald's, The Great Gatsby, is another. There are many other ones as well that I found to be utterly boring in my younger years only to fall in love with them as I grew older and "rediscovered" them. I think the problem with a lot of modern books are that they lack the kind of "density" of the older classics, which makes them entertaining to read, but ultimately forgettable. I would struggle to name any contemporary books or authors that would ever be able to hold a candle to some of the classics. Who knows, though, maybe a hundred years from now the books that we currently dismiss as disposable entertainment will have become the "new" classics.
I don't have a lot of answers to this one because due to the amount of books that I read there just isn't time to read anything more than once, especially if it didn't "grab" me the first time round. The only time that this has ever happened really was with a book called "Middlemarch" that was written by George Eliot. The problem I had when I read the book the first time was that I was young and the book was already old, so I never managed to connect with it in any way. The themes that are explored in the book were also a little too complex for my teenage brain to fully process. It was only many years later when my flatmate started reading the book and raving about it that I got the urge to try and read it again. I was actually getting quite annoyed with her for constantly telling me how good the book is for an "old" book because I had read it and didn't think it was special at all. Upon re-reading the book I discovered themes I never noticed before and also discovered that some of the characters who in my mind were boring or unrelatable were now actually becoming my favorites. I strongly encourage everyone to read this book and if you have already and didn't like it, then maybe you just needed a bit more experience in life to fully appreciate it.
A lot of people have mentioned it already, but it really is the classic books that only become better with age and upon re-reading. That is one of the reasons why I keep returning to this site as I can easily get all those half remembered and semi forgotten classics to read again on my phone. Sometimes some of the books are as bad or boring as I remember from my days being forced to read them at school, but most of the time a book turns out to be even better than what I remembered or so much better than what I thought. What I have also found is that while it shouldn't really matter, the look of a book can also shape my opinion. Many classic books are like these dusty, moldy looking things when you find them a secondhand bookshop, but if you see them digitally with a new cover they almost look more appealing. This is just a personal observation of course and your mileage may vary.
Animal Farm by George Orwell springs to mind as I don't think I got all of the subtext of this book when I read it the first time as a youngster. I did find it very funny when the animals in the book banded together and chased all of the humans off the farm. The Battle of the Cowshed was also quite entertaining to read. It wasn't until I was much older and saw people discussing Animal Farm that things began to fall into place for me and I saw the book for what it really is. Another book that perplexed me a lot when I was younger, but finally made a lot more sense when I read it as an adult was The Metamorphosis by Franz Kafka.
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