Good books are good people: Books are people speaking with signs. Meeting cool people several times is nice.
Choose books like you choose your friends. Talk to many, stick with the best. A good book can make you happy, get you through hard times, teach you amazing stuff. It can do that every time you read it. Meeting good friends again and again is where the fun starts: Good books are a pleasure to read. Repetition of pleasure is fun.
Good friends are never boring: Do you think that if you read Kant’s “Critique of the Pure Reason” you’d get it all in one go? Kant would not.
Good stories are never fully understood: Do you think that if you read “A Midsummer Night’s Dream” you’d get it all in one go? Shakespeare would not.
Good stories gain through repetition: You learn more reading “The postman always rings twice” for the 3rd time than losing the pleasure of reading over some boring “must read” classic that doesn’t talk to you.
Repetition is sweet: Imagine a guy that eats his favorite meal just one time, because he is “afraid to get bored”; or he “doesn’t have the time to eat the same thing twice”. Kids love repetition. Why do you think that is? This doesn’t only apply to books. It applies to all content. Try and read a blog entry you really liked—again. If you enjoy it as much or even more than the first time, it’s a good piece of work. If you’re bored—it’s not. All you have to do to find out if this theory works is to overcome your initial resistance.