| Quote #1
Well, what about books? Well, precisely because you have denied [pleasure] in every other field, you believe you may still grant yourself legitimately this youthful pleasure of expectation in a carefully circumscribed area like the field of books, where you can be lucky or unlucky, but the risk of disappointment isn't serious. (1.6)
Shmooper, meet yourself. Yep—this passage introduces you to yourself as "You, the Reader," which is the position you'll occupy for most of the novel. It tells you that you tend to be very conservative with pleasure; in other words, you tend to avoid displeasure more than you pursue pleasure. Why? Because you're afraid of disappointment. The only true pursuit of pleasure you'll allow yourself comes in books, since in books there is no serious threat of disappointment. It's a safe place where you can pursue pleasure. It's nothing nearly as scary as asking someone on a date in real life.
| Quote #2
So here you are now, ready to attack the first lines of the first page. You prepare to recognize the unmistakable tone of the author. No. You don't recognize it at all […] Are you disappointed? Let's see. Perhaps at first you feel a bit lost, as when a person appears who, from the name, you identified with a certain face, and you try to make the features you are seeing tally with those you had in mind, and it won't work. (1.21)
You sit down and start reading If on a winter's night a traveler, only to find out that the tone and style of the book is nothing like what you expected. In modern reading, an author's tone can be like a specific brand of product that you buy, and it comes with certain expectations from the reader. When the narrator asks whether you're disappointed, Calvino is hinting toward the fact that any expectations you have going into a book are things you should avoid. It's better to just read with an open mind. Calvino later takes on this idea of an author having many different styles of writing by beginning ten different novels in ten very different styles. In other words, the book will go on to frustrate your expectations as a reader specifically because it doesn't want you to have any.
| Quote #3
The thing that most exasperates you is to find yourself at the mercy of the fortuitous, the aleatory, the random, in things and in human actions—carelessness, approximation, imprecision, whether your own or others'. In such instances your dominant passion is the impatience to erase the disturbing effects of that arbitrariness or distraction, to re-establish the normal course of events. (3.5)
You've been interrupted in your reading of If on a winter's night a traveler after discovering that the book's first chapter is just repeated over and over again. And guess what? It's occurred at the very moment when you are most desperate to keep reading. The thing that disappoints you most about this problem is that it is based on a completely random error: a bungled job at the printing house. See, you seek pleasure in reading because there is a recognizable order to it, and you don't like when something random interrupts your well-ordered life and well-ordered pleasure. You immediately become impatient to set things right again, to have the world make sense. You want life to unfold in front of you in a logical, straightforward way. But that's not what you always get in life—and apparently, not in reading either.