Where and when does Montag steal his first book in Fahrenheit 451?  

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In Fahrenheit 451, Bradbury does not reveal where and when Montag stole his first book. Early in the book, he hints at Montag's stolen book collection at several points, like when the Mechanical Hound growls at him in the firehouse:

"If someone here in the firehouse knew about the ventilator then mightn't they "tell" the Hound . . . ?"

After Captain Beatty visits his house, Montag finally unveils his collection to his very shocked wife, Mildred. In total, Montag takes "some twenty books" from behind the grille before apologising to Mildred and then asking her to read them with him.

So, when Montag steals a book from the lady whose house he burns, it is not the first time. By not revealing when and where he first stole a book, Bradbury implies that Montag has been dissatisfied with the status quo for some time but needs a little encouragement. This is why his meeting with Clarisse is so significant. 

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At first, it seems like Montag steals his first book during a raid on an old woman's home, where she is revealed to be a book-hoarder. He is inspired to do this by the circumstances, and by the changes in his outlook on life and society brought on by self-reflection and his conversations with Clarice and Beatty.

Tipped off by her neighbors, the firemen arrive at the old woman's home with the conviction that the books must be hidden in her attic. The woman appears resigned and cooperative in a passive-aggressive manner, and the firemen begin to break down the doors and walls of the house with axes, despite knowing they are unlocked, and Montag is caught between the ground floor and the other firemen shoveling the books down onto him. One falls into his arms, and he hides it on his person, not really knowing why, only that it's evident that in the chaos of this moment he might be able to get away with it. 

Later in the story, it is revealed that the book he stole from the old woman's home was not actually his first. We learn that Montag has been amassing a collection of stolen books for quite some time, though we are never told when he actually stole his first one.



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