grammaboodawg
Immortal
Here's a Book Spoiler of the condensed story of Bilbo and Gollum's first meeting and how the game is played... for a moment of Tolkien-zen.
... Since he was lost in the dark without hope... ...Bilbo accepted the challenge; and they asked one another many riddles. In the end Bilbo won the game, more by luck (as it seemed) than by wits; for he was stumped at last for a riddle to ask, and cried out, as his hand came upon the ring he had picked up and forgotten: What have I got in my pocket? This Gollum failed to answer, though he demanded three guesses.
... The Authorities, it is true, differ whether this last question was a mere 'question' and not a 'riddle' according to the strict rules of the Game; but all agree that, after accepting it and trying to guess the answer, Gollum was bound by his promise. And Bilbo pressed him to keep his word... ...this slimy creature might prove false, even though such promises were held sacred, and of old all but the wickedest things feared to break them. But after ages alone in the dark Gollum's heart was black, and treachery was in it. He slipped away, and returned to his island, of which Bilbo knew nothing, not far off in the dark water. There, he thought, lay his ring. He was hungry now, and angry, and once his 'precious' was with him he would not fear any weapon at all.
... But the ring was not on the island; he had lost it, it was gone.'"
Of the Finding of the Ring: Prologue: The Appendices: The Return of the King
..."'Maybe he would have attacked Bilbo at once, if the ring had been on him when they met; but it was not, and the hobbit held in his hand an Elvish knife... ...as a sword. So to gain time Gollum challenged Bilbo to the Riddle-game, saying that if he asked a riddle which Bilbo could not guess, then he would kill him and eat him; but if Bilbo defeated him, then he would do as Bilbo wished: he would lead him to a way out of the tunnels. ... Since he was lost in the dark without hope... ...Bilbo accepted the challenge; and they asked one another many riddles. In the end Bilbo won the game, more by luck (as it seemed) than by wits; for he was stumped at last for a riddle to ask, and cried out, as his hand came upon the ring he had picked up and forgotten: What have I got in my pocket? This Gollum failed to answer, though he demanded three guesses.
... The Authorities, it is true, differ whether this last question was a mere 'question' and not a 'riddle' according to the strict rules of the Game; but all agree that, after accepting it and trying to guess the answer, Gollum was bound by his promise. And Bilbo pressed him to keep his word... ...this slimy creature might prove false, even though such promises were held sacred, and of old all but the wickedest things feared to break them. But after ages alone in the dark Gollum's heart was black, and treachery was in it. He slipped away, and returned to his island, of which Bilbo knew nothing, not far off in the dark water. There, he thought, lay his ring. He was hungry now, and angry, and once his 'precious' was with him he would not fear any weapon at all.
... But the ring was not on the island; he had lost it, it was gone.'"