1. Maybe he thought they would be the best of them to carry on the quest if anything happened to the rest.

2. Overall he did well and held his own and eventually got away again.

4. I don't think Smaug realized that there was a vulnerable spot; that is why he showed his underside to Bilbo without any qualms.

1. I suppose it has to do with the fact that they are Thorin's near relations and heirs? It is worth noting that Thorin went himself to help with the rescue.

2. As the dwarves say, it's not everyone who can claim to have talked to a dragon and live to tell about it!

3a. I've always thought them quite clever to come up with on the spur of the moment; it's probably a bit like Catchphrase where you can't say the word to describe what you're thinking of!

3b. They made Smaug more interested in talking than catching Bilbo?

5. Because the Arkenstone is the best of the best, unique, and a family heirloom.

1. When Smaug first leaves the mountain to attack, Thorin sends Balin, Kili, Fili, and Bilbo inside while the rest rescue Bofur and Bombur. Why do you think he chose those four to be safe? I think he sent Fili and Kili because they are close relatives to him. Bilbo wouldn't have been much help because of his size. It might also have something to do with the respect he had earned. Balin and Thorin were the only two familiar with the area. The group inside would benefit from his knowledge.
2. How well do you think Bilbo handled his encounter with the dragon? Overall he did a good job. He came back alive. He made a few mistakes, such as giving enough information so Smaug knew the people of Laketown had helped them. (Smaug had suspected.) He also made Smaug angry which caused Smaug to burn him.
3. What do you think of Bilbo's riddles? Why were they so important? What do you think of Smaug's response to them?The riddles are fairly clever, especially since he had to think of them on the spot. They fascinated Smaug. They also gave Smaug information that probably should have been hidden (ex. the number of the dwarves). Smaug's first Repeated Word two responses were harsh. However, he softens as Bilbo goes on - first he sneered, then he scoffed, finally he said, "That's better." It is interesting that he tells Bilbo not to let his imagination run away with him right after Tolkien describes Bilbo as "beginning to be pleased with his riddling." Did Smaug notice that Bilbo was beginning to feel proud? He might have said that so Bilbo wouldn't get too confident. I would think dragons would prefer nervous guests.
4. What do you think of Smaug's folly of revealing his waistcoat? It shows his pride and confidence. He and Bilbo both did a bit of showing off, and it was detrimental to both of them.
5. Thorin seems to have an obsession with the Arkenstone. Why do you think he treasures it so? It is one of a kind and large. They call it the heart of the mountain so it might also be symbolic - whoever possesses it controls the mountain.

1. Well, Balin was one of the older dwarves and he had some knowledge of the mountain's insides, Fili and Kili were two of the youngest and Thorin's sister-sons (not just general relations, kind of a particular special relationship), and Bilbo was just the burglar, with no battle experience and a Hobbit to boot.

2. I thought he handled it fairly well. Like Twig's said, Bilbo did perhaps talk more than he should, but all in all it went pretty well.

3. Bilbo's riddles here were clever than they were when he was riddling Gollum. I'm not sure their exact importance here except it ties back as a nice comparison/contrast to the riddle game with Gollum, and it helps show the differences between Smaug and Gollum, and how Bilbo has changed.

4. It was a folly, but it fits since Smaug was so proud, and it was good for Bilbo to see that Smaug did indeed have a weakness.

5. Because it's the sign of divine right of kingship! Seriously, it is a gorgeous stone, and we already know that Dwarves (and Elves!) have a great lust for precious things; I think the Arkenstone had kind of been denoted as being fit for a king, and Thorin would indeed think that he should have it as king.

1. When Smaug first leaves the mountain to attack, Thorin sends Balin, Kili, Fili, and Bilbo inside while the rest rescue Bofur and Bombur. Why do you think he chose those four to be safe?

He needs Bilbo, because Bilbo is the burglar. Fili and Kili are the youngest, as well as his relatives. And Balin is the oldest, so... respect for one's elders, maybe?

2. How well do you think Bilbo handled his encounter with the dragon?

I think he handled it quite well, considering what a fearful situation it must have been for him. Much better than most of us would have done, I dare say.

3. What do you think of Bilbo's riddles? Why were they so important? What do you think of Smaug's response to them?

I think both of them were brilliant. It's actually one of my favorite scenes in the book. I love the double meanings to the things Bilbo says, especially.

4. What do you think of Smaug's folly of revealing his waistcoat?

I think it resulted from pride. Pride has been the downfall of many a villain.

5. Thorin seems to have an obsession with the Arkenstone. Why do you think he treasures it so?

It is most likely more valuable than the other treasures that he had. I've often heard theories that it could be a Silmaril, but I don't know if that theory is valid at all.

~Riella

I've often heard theories that [the Arkenstone] could be a Silmaril, but I don't know if that theory is valid at all.

Geographically speaking, I think that highly unlikely. We can remove Earendil's stone from the reckoning because he still carried it over Middle-Earth. One was cast into the sea (before the sundering, I think, which would put the coast way beyond the Grey Havens) and the other was cast into a fiery crevasse. Even supposing the one in the sea was washed up under the Lonely Mountain, that would be quite the trip up and around to the north to get into the River Running...

1. Simple. He wanted to protect those four. Balin was the oldest, Fili and Kili the youngest, and Bilbo was the smallest, the idea-man, and the only non-Dwarf of the company.

The alternate theory that they might be the four least able to help is also plausible.

2. Mixed results. He was noticed despite being invisible. He survived the encounter alive, although singed. He discovered the dragon's weakness, though he had no immediate way to exploit it. He gained intelligence on how much Smaug had discovered about his party, but gave away more information about his party in the discussion. Overall I guess I would call it a draw since there is no real indication that Bilbo learned more about Smaug than Smaug did of Bilbo.

3. I think Bilbo painted a rather grand picture of himself but the riddles are fairly accurate. They served to keep the dragon interested enough in the conversation to keep Bilbo alive while they were having it.

4. It was a foolish move indeed. Smaug must have been a proud creature. Did Smaug not know there was a bare patch in his armor or did he feel like it was such an insignificant weakness that he didn't mind showing it? Perhaps Smaug was quite confident that Bilbo would be dead by the end of the conversation so he didn't mind what Bilbo learned.

5. He is a dwarf. It is the most magnificent jewel in middle earth. The attraction is understandable. Also the fact that it is a family heirloom would make it precious to him.

6. When Bilbo was sent down to steal from the dragon, do you think the dwarves honestly expected never to see Bilbo again? What about the second time Bilbo went down?

When Bilbo was sent down to steal from the dragon, do you think the dwarves honestly expected never to see Bilbo again?

From the text I infer that Balin, at least, was quite surprised and delighted to see Bilbo again.

So perhaps the dwarves that had never actually seen a dragon (were there some, or am I confusing movie extrapolation with canon?) thought Bilbo would come through all right but those who saw Smaug come, when it came down to the point, didn't believe Bilbo would make it out alive.

So perhaps the dwarves that had never actually seen a dragon (were there some, or am I confusing movie extrapolation with canon?) thought Bilbo would come through all right but those who saw Smaug come, when it came down to the point, didn't believe Bilbo would make it out alive.

I have assumed that Fili and Kili, as the youngest, were not around when the dragon attacked a few hundred years back.
It's even possible that some of the others were not in the city on that day - perhaps didn't even live there at the time?

It's quite possible that it would be those who knew nothing about dragons that would think lightly of it and assume that everything would be fine - while those who knew more about what a dragon could do, had little to no hope about Bilbo's survival.

3a. What do you think of Bilbo's riddles?

Someone else said that they were good, considering that they had to be made up on the spur of the moment, and I agree.
Bilbo got a bit carried away by his own ingenuiety, though. He thought it was fun to get closer and closer to the truth without actually revealing it - and he got closer than he ought to.

4. What do you think of Smaug's folly of revealing his waistcoat?

It was unintended and rather unfortunate for him. He surely didn't know about the hole - I guess it was in an awkward position which he couldn't easily see - I'm sure he wouldn't feel so sure about himself that he would show off, feeling sure that nobody could take advantage of his vulnerability.

It was very fortunate for Bilbo and the others, though ...