1. Did Bilbo cheat? If yes, what does that say about his character?

He did cheat, though he came upon it inadvertently (asking himself what was in his pockets). The cheating, if we can call it that, was insisting that the question be allowed as a riddle.

Still, considering he feared for his life (and, rather ironically, expected Gollum to cheat), it's understandable that he took this way out of what was a very dangerous situation.

2. Chance or luck?

It was the author manipulating his characters. More seriously, the Ring seems to have the ability to get things done its way, so to speak.

3. Left behind intentionally?

Maybe they figured such a small creature wouldn't offer much meat?

4. Perhaps he associated his proper appearance - including the buttons (as part of his clothing) as a connection to his hobbit-hole, with all its comforts and its laid-back way of life. Their loss could symbolize the beginning of his separation from that life; even though he returns home after the adventure, it leaves him changed.

What do you think about the fairness of the outcome of the game? Did Bilbo cheat? If yes, what does that say about his character?

I would say yes and no as to the cheating. I reread that passage yesterday and and it does say that Bilbo was talking out loud but to himself in regards to the ring. So he did not intend that as the next riddle but since Gollum took (no pun intented ) it that way, Bilbo did go along as well.

So technically it was not quite a riddle but he also aloud the 3 guesses which might not have been allowed under the normal rules. So there is a bit of balance in what happened.

And the fact that Bilbo was fighting for his life and Gollum was now so close to him would give some allowances due to the desperate situation.

Interesting Chapter (5), "Riddles in the Dark".

Anyone want to venture a thought or two on what riddle-games Tolkien was referring to when he mentioned that it was of "immense antiquity"?

What do you think about the fairness of the outcome of the game? Did Bilbo cheat? If yes, what does that say about his character?

I lean toward the view that both played as fairly as possible when they made up the end game as they went along... Once Gollum accepted "What have I got in my pockets?" as a question it ought to have been honored. On the other hand, surely Bilbo could have come up with something more riddle-like even if it was only "What's brown and sticky?"

Spoiler

A stick--you knew that.

I'm also trying to think if I can make a convincing case for Gollum being the more honorable of the two because he did show Bilbo the way out. But since Bilbo answering, "Oh, just a ring I found on the ground" seems likely to have resulted in Gollum eating him I can't quite bring myself to make that case.

Chance or luck?

I quite like 'gazer's answer. Since I can't guess at how the story would have had a happy ending without Bilbo's finding the ring of power, I guess I'll go with a generous pinch of luck.

How could they have missed seeing Bilbo, then?

I imagine he sort of fell into a corner right as the goblins were rushing by and they had a larger target in sight.

Why do you think Bilbo's buttons were so important to him?

Because they represented his status as a respectable hobbit.

1. I think both Bilbo and Gollum cheated a little. It's very easy to accidentally mislead someone or "cheat" (such as Bilbo with not asking a real riddle) without meaning to, but it's very hard to admit your mistake and back up, especially when you're terrified of being eaten. I think it shows Bilbo as being a very, well, human character, for lack of a better description.

2. Other forces! As you all have mentioned, the One Ring has a will of its own. But I also wonder if there wasn't some good force or providence at work here (I suppose that could fall under 'luck') - after all, Bilbo made it out safely and
3. I'm guessing that Bilbo just got missed since the Goblins were in a rush and they were after the rest of the Dwarves. I also have an impression that Bilbo was just rather miss-able for the first half of the adventure.

4. Like the rest of you, I think Bilbo's buttons are part of him being properly dressed and respectable. In chapter 7,
Oh, and Mel, I can't place hearing about any of the old riddle games. I have half of an idea of it occurring in some legends or folk or fairy tales, but I'm not sure which. Unless Rumplestiltskin, with the guessing of names, counts?

1. I am of the mind that once Gollum accepted it as a proper question, it became fair. It may indeed be true that it wasn't a fair question, but after Gollum's four guesses (when three were agreed upon and only one is fair for a riddle game) was too late for Gollum to properly dispute it. Had he been thinking properly, he should have insisted upon another question before agreeing to the challenge of answering it. But I rather think that Gollum would have cheated anyway even if everything Bilbo had done was official, and that makes some of this discussion of fairness a bit moot.

It could be argued that the more underhanded deeds done by Bilbo in this chapter (and all successive chapters) was done under the influence of the ring. More likely, it was done under survival instinct. (After all, Bilbo didn't have much time to think about the morality of any of his actions.) Yes, it is possible that Bilbo cheated at the riddle game, and even worse, in effect, stole the ring from Gollum by not returning it to him once he understood it was his, (but by this time Gollum and Bilbo were clearly enemies in a battle of life and death, and so perhaps rules of spoil take effect?) but the true test of Bilbo's sense of fairness comes when, invisible in the dark and with a sword in his hand, Bilbo has the chance to slay Gollum then and there but does not. I think it is in this chapter that we see Bilbo both at his worst, and at his best.

2. I think the ring definitely had a will of its own. It wanted out of Gollum's cave and was content enough to have Bilbo carry it out. But then it wanted away from Bilbo as well, as evidenced by its slipping off Bilbo's finger before reaching the back door. I think the ring wanted to be found by a goblin, and did everything in its power to have been so. But there were other forces at work, besides those of evil. Bilbo was meant to find the ring, and despite what the Necromancer wished, things were working out for good.

3. I think most goblins had simply missed Bilbo, despite having keen vision in the dark. Others who saw him alive might have thought the dwarves a more urgent foe to face or Gandalf a more important foe to face. Still others might have thought Bilbo already dead. When in the middle of a battle, one tends not to take much notice of the fallen, regardless of the reason they fell.

4. I simply think that Bilbo's Bagginishness was being stripped away from him, bit by bit, allowing the Tookish part of him to come forward. Losing his buttons was one episode in this process. There are others. Running out his front door, without his handkerchief, to go on an adventure was the first. Going without meals were others. Trying to pick-pocket a troll was yet another.

I think we are meant to think that the worst parts of Bilbo are his most hobbity parts, such as his lust for food and comfort, (gluttony some might call it). It may have started out as a simple appreciation, but for some hobbits grows into an obsession, and even Bilbo, who is strong enough to understand that other things are more important than food, still gets the grumpiest and most ill-natured when he is deprived of and thinking of home and food. (Something akin to Jill and Eustace when they are thinking of food and hot baths at Harfang.) The worst part of the dwarves are their dwarvish greed, and the worst part of men are their human lust for power. But Tolkien also lists good traits for each race, (the stealth and goodness of the hobbits, the heartiness and steadfastness of the dwarves, the inner strength of man) and suggests that everyone has the ability to rise up and be greater than base habits would make us out to be.

1. What do you think about the fairness of the outcome of the game? Did Bilbo cheat? If yes, what does that say about his character?
I don't think Bilbo's question was fair. He didn't mean to ask the question but he didn't try to get out of it. I suppose fear was the main motivation for his not trying to get out of it. Gollum knew the question wasn't fair but he answered it anyway. Apparently Bilbo was more afraid of Gollum than of cheating at the riddle game. It would be very interesting to know exactly what the ancient law stated. In the end Gollum kept his promise inadvertently. For the record, I don't think Bilbo deserved to be eaten but he should have come up with another riddle. (And Gollum should have demanded it.)
2. Several things in this chapter seemed to happen by chance or by luck. Do you think it was luck or are there other forces at work?I can't help thinking about what the Hermit says in HHB about there being no such thing as luck. What is considered luck is often part of a bigger plan.
3. How could they have missed seeing Bilbo, then? Could he have been purposefully left behind? I'm sure the goblins did not leave him on purpose. I assume he fell off to the side. Maybe he fell behind the rock he hit his head on. Bilbo fell because Dori was grabbed so the goblins didn't have their hands on him. After they grabbed Dori, they would have been quite busy fighting. After the attack, they might not have gone that way or were not looking for him. They probably thought everyone had escaped.
4. Why do you think Bilbo's buttons were so important to him? What was the impact of losing them? What changes in Bilbo's character could this symbolize?
It sounds like they were nice buttons. The goblins thought they were worth collecting. The are a luxury that ties him to his respectable life. He now looks the part of the adventurer and burglar.

I recently noticed something about the Riddles that Bilbo and Gollum asked each other. It comes in a contrast of the riddles they ask. The answer to Bilbo's questions are all homey, personal and warm sorts of things--teeth, sun on the daisies, eggs, a man eating a fish for diner and giving the cat the bones. In contrast, Gollum's riddles all have big, cold, wide-world answers--the mountain, wind, darkness, and time. The only exception to this, is one of Gollum's riddles is answered with "fish", which is still a rather cold and lonesome thing.

I think it is interesting that Gollum's questions all deal with wild, cold things, while Bilbo's all deal with warm, homey things. At the same time, Gollum doesn't like remembering his home when he was less sneaky, as Tolkien puts it, and Bilbo doesn't exactly care for being in a dark hole and about to be eaten.

It was an interesting contrast that I just realized. Not sure that it has much else to do with the book, just an interesting expression of what the two characters, or even what the two hobbits, value, and how they differ.

What do you think about the fairness of the outcome of the game? Did Bilbo cheat? If yes, what does that say about his character?

I don't believe Bilbo meant to cheat; but he did cheat, it could be said, by accident. It was due to a misunderstanding that Bilbo didn't bother to correct, because he knew it could save his life. I don't think it says anything negative about his character. He's a very honest Hobbit. And truth be told, even if he had cheated, I still wouldn't believe it came from any bad part of his heart. Gollum was trying to kill him. It's one thing to play a game. It's an entirely different thing to play a game with a murderer when your life is at stake.

2. Several things in this chapter seemed to happen by chance or by luck. Do you think it was luck or are there other forces at work?

Although there aren't very overt mentions of God in Tolkien's works, there are many allusions to him working things for good. So yes, I do believe there are other forces at work.

3. The goblins have very good eyesight in the dark, and the best of the best had been sent after Gandalf and the company. How could they have missed seeing Bilbo, then? Could he have been purposefully left behind?

I doubt it was on purpose. They most likely didn't notice him due to all the scuffle.

4. Why do you think Bilbo's buttons were so important to him? What was the impact of losing them? What changes in Bilbo's character could this symbolize?

When you leave everything, what little possessions you do have with you become much more important. They're a little bit of home. Losing them would only remind him that he may never be able to go back to the life he had before.

~Riella

2. Several things in this chapter seemed to happen by chance or by luck. Do you think it was luck or are there other forces at work?

There are other forces at work. Gandalf talks about it in The Lord of the Rings, when he tells Frodo about how the Ring was made by Sauron, and how it got to Bilbo. He says that the Ring was trying to get back to its master - implying that the Ring had a will of its own, which is also indicated by it sometimes falling off a finger. Then he goes on,

Behind that there was something else at work, beyond any design of the Ring-maker. I can put it no plainer than by saying that Bilbo was meant to find the Ring, and not by its maker.

Ithilwen said,

Although there aren't very overt mentions of God in Tolkien's works, there are many allusions to him working things for good.

It's not a very overt mention - but I believe this is one of those many allusions. So definitely other forces at work.