Cunning and Cleverness Quotes in The Hobbit, or, There and Back Again

How we cite our quotes: Citations follow this format: (Chapter.Paragraph)

Quote #1

A really first-class and legendary burglar would at this point have picked the trolls' pockets – it is nearly always worth while, if you can manage it –, pinched the very mutton off the spits, purloined the beer, and walked off without their noticing him. Others more practical but with less professional pride would perhaps have stuck a dagger into each of them before they observed it. Then the night could have been spent cheerily.

Bilbo knew it. He had read a good many things he had never seen or done. He was very much alarmed, as well as disgusted; he wished himself a hundred miles away, and yet – and yet somehow he could not go straight back to Thorin and Company emptyhanded. (2.42-3)

The thing is, Bilbo has no practical experience of the outside world by the time he finds his first real adventure with the trolls in the forest. But he has read a lot of tales and legends, so he knows how his story is supposed to go. He decides that, as a burglar, he has to pick Bill the Troll's pocket – he can't go back to Thorin "emptyhanded." And, of course, he winds up getting captured. Are there other examples in The Hobbit where Bilbo makes decisions based on his assumptions or other people's expectations? Or does he learn his lesson with this trollish disaster? What can Bilbo's decision in this passage tell us about his character at this point of the novel?

Quote #2

[Gollum] was anxious to appear friendly, at any rate for the moment, and until he found out more about the sword and the hobbit, whether he was quite alone really, whether he was good to eat, and whether Gollum was really hungry. Riddles were all he could think of. Asking them, and sometimes guessing them, had been the only game he had every played with other funny creatures sitting in their holes in the long, long ago, before he lost all of his friends and was driven away, alone, and crept down, down, into the dark under the mountains. (5.22)

Gollum is trying to stall while he has Bilbo right in front of him, so he challenges the hobbit to a riddle game. Why do you think Bilbo agrees? What might have happened if Bilbo had refused to riddle with Gollum? What does this passage in the novel show us about Gollum's character?

Quote #3

[Bilbo] knew, of course, that the riddle-game was sacred and of immense antiquity, and even wicked creatures were afraid to cheat when they played at it. But he felt he could not trust this slimy thing [Gollum] to keep any promise at a pinch. (5.68)

It strikes us as a little odd that Tolkien spends so much time describing the riddle game when the end result doesn't matter: if Bilbo loses, Gollum will try to eat him. And now that Bilbo has won, Gollum is still going to try and kill him. What's the tone of the riddle chapter in The Hobbit? What does it achieve in the novel's plot and character development?