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How does Gandalf trick the trolls in The Hobbit?

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Gandalf tricks Bilbo into wanting to go on an adventure by twisting his own words around and invoking his Took ancestry. The dwarves contribute by singing stimulating songs about journeys to distant lands and then leaving without him.

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Gandalf tricks the trolls by impersonating, or mimicking, the other trolls' voices.  By pretending to be William, Bert, or Tom, he stirs up conflict with the other trolls, making them argue and forget their original purpose of killing and eating their captives.  Gandalf's clever trickery distracts the trolls enough that they do not realize that dawn approaches, and when the sun rises, the trolls immediately turn to stone, thus freeing the dwarves and Bilbo. This humorous scene serves multiple purposes in the text:  1) Tolkien injects humor into what could be a frightening scenario; 2) Tolkien also builds on his characterization of Gandalf as a very clever and quick-witted guide. 

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How do Gandalf and the dwarves trick Bilbo into an adventure in The Hobbit?

In The Hobbit , Bilbo Baggins is primarily portrayed as a cautious, staid, and even fussy hobbit. The Baggins family, even more than many other hobbit clans, loves the comforts of home. Bilbo never explicitly states that he...

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has any desire to go on an adventure. Instead, it seems that adventure comes looking for him. After the wizard Gandalf finds him in the Shire and marks his door so a group of dwarves will arrive at his hobbit-hole, he finds himself caught up in the excitement they generate. Before he knew it, he “found himself doing and saying things altogether unexpected.” The maternal side of Bilbo’s lineage is the Tooks, who had been known to do daring things. The things he hears from Gandalf and the dwarves awaken “something Tookish” with him.

When Bilbo meets Gandalf, the wizard’s reputation has preceded him. Impressed, the hobbit starts fawning over him as having inspired “quiet lads and lasses going off into the blue for mad adventures.” Gandalf quickly seizes on this enthusiasm and claims that Bilbo is asking to go on an adventure himself.

The dwarves at first seem unconvinced that Bilbo, who looks like “a grocer,” is the one they are seeking. As they eat, drink, and sing loudly in his home, Bilbo gets caught up in the exciting mood. “Far over the misty mountains” begins to seem like a desirable destination. Now he wants “to go and see the great mountains … and explore the caves.” While Thorin’s speech frightens him, Gloin’s disparaging remarks stimulate him to declare that he is more than up to the task. After the raucous party, when he wakes up the next day, they are already gone. Bilbo quickly decides that he must join them.

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