Bilbo wakes up and finds himself alone in a cold, dark cave. He finds a small ring on the ground, and puts it in his pocket almost without thinking. Though he doesn’t know it at the time, this is a turning point in his life. He looks in his pockets for a pipe or tobacco, but finds nothing, though under his coat he finds the knife he took from the trolls. He realizes that it’s been made by elves, since it glows when goblins are nearby. Thinking that it’s a great thing to own an old, beautiful weapon, he resolves to go forward, though he’s afraid.
Events have caused Bilbo to be alone, forcing him to begin to take control of his life: he resolves to move forward with his weapon instead of cowering in the dark. That his weapon has an elven-made history and he, as holder of the sword, inherits that history, also gives him a sense of security. The ring he finds, apparently by accident, will indeed be important to his success—in retrospect, this suggests that successful adventuring isn’t always due to the individual’s abilities. Sometimes luck—or fate—is equally, if not more important. Yet the way he finds the ring mirrors the way he finds the keys to the Troll treasure. Bilbo seems to be someone who happens to find things. And, of course, it being treasure, he pockets it: Bilbo is not immune to greed for beautiful things like rings and beautiful swords.
Bilbo is in a “tight place,” the narrator notes, but he has the advantage of being used to living underground in holes. Bilbo walks for a long time, until he’s very tired. Eventually, when his sword is barely glowing at all, he comes to a cold, slimy pool.
Bilbo’s experiences in his home prepare him well for his adventures here underground (which also functions as a way to connect him to establish the soon-to-be-introduced Gollum as a kind of double to Bilbo). He courageously continues to walk into the darkness.
A small, slimy creature called Gollum lives by the pool. Gollum hides from the goblins, though he eats goblin when he can get it, and also eats fish. He paddles through the water in a small boat, and notices Bilbo before Bilbo notices him. Gollum thinks that Bilbo, who’s clearly not a goblin, would make a good meal.
The narrator makes it clear almost immediately that Gollum is a threat to Bilbo; and Gollum is clearly a very bad host, who is not at all generous with his “guest,” Bilbo. Tolkien also more firmly establishes the doubling between Bilbo and Gollum by pointing out some similarities between them: both are obsessed with eating. It’s as if Bilbo is confronting a darker version of himself.
Bilbo becomes aware of Gollum and, frightened, points his sword at him. Gollum, who always talks to himself, asks what Bilbo is; Bilbo replies that he’s a hobbit. Gollum shifts his plan when he realizes that Bilbo is armed. Rather than attack, he asks Bilbo to stay a while and tell riddles, as he remembers doing years ago, when he lived in the sun and had friends. Gollum tells Bilbo an easy riddle, and when Bilbo answers it, Gollum suggests that they have a competition: if Gollum can stump Bilbo, he eats Bilbo; if Bilbo can stump Gollum, Gollum will show Bilbo the way out of the cave. Bilbo is too afraid to disagree with these terms.
Gollum lives in utter solitude— he lives on the exaggerated edge of the spectrum of someone who is so homebound that he never interacts with the world he never leaves his home, exemplified in the fact that he talks only to himself.. Bilbo, in contrast, has left his home and interacted with the world. Note Bilbo’s improved use of language as he engages in a high-stakes game of riddling. Once again, the immediate danger of the situation forces him to grow into something of a different person (or hobbit) than he was before.
Bilbo and Gollum tell each other a series of riddles. Bilbo’s riddles have answers that reflect his life in hobbit-town: the sun, flowers, eggs, etc. Gollum tells riddles about the things he’s most familiar with: the dark, fish, the wind, etc. Though Gollum and Bilbo have trouble guessing each other’s riddles, they trade correct answers for four rounds without a winner. Finally, after Bilbo correctly answers Gollum’s fifth question, the only question Bilbo can come up with is to ask Gollum what he, Bilbo, has in his pocket (the ring); Gollum asks for three guesses, but can’t come up with the right answer, and thus loses the game. Bilbo knows that riddle-telling is an ancient, sacred art, and even Gollum won’t break the rules they’ve agreed upon. Still, he’s nervous around Gollum, since he won on a question that wasn’t a proper riddle.
Language is a powerful weapon—Gollum is literally using it to try to kill Bilbo, while Bilbo is using it to save his life. Language is also a reflection of a speaker’s innermost thoughts and experiences: Bilbo’s and Gollum’s riddles reflect the kind of person each is and the experiences each has had. Language is also a sacred art, and both Bilbo and Gollum seem to abide by the rules of the riddle-telling game. It’s worth bearing in mind, however, that Bilbo isn’t yet a master of language—he quickly runs out of riddles to tell, and ends up asking Gollum such a casual question that it doesn’t follow the sacred code of riddling, and thus puts Bilbo’s life in danger.
Gollum says that he’ll show Bilbo the way out, but first he must paddle back to his lair and retrieve some things. Gollum actually intends to retrieve his ring, which makes him invisible, and use it to turn invisible and then kill Bilbo. The narrator says that no one knows how Gollum first found the ring, long ago, but that he wears it frequently, and uses it to catch his prey. But when Gollum goes back to his lair, he discovers that the ring is missing. He paddles back to Bilbo, and demands to know what Bilbo had in his pocket. Bilbo refuses to answer the question, and asks Gollum what he has lost, having heard him wailing earlier. Gollum refuses to answer Bilbo’s question.
Tolkien shows us that Gollum is evil because he breaks a verbal promise to show Bilbo the way out—though he claims he’ll help Bilbo, he secretly wants to eat him. In a sense, Gollum is evil because he is a host so bad he wants to eat his guest. Yet the doubling between Bilbo and Gollum also intensifies here as it becomes clear to the reader (though not entirely to Bilbo) that Bilbo has actually inadvertently stolen Gollum’s ring. Gollum’s demand to know what’s in Bilbo’s pocket and Bilbo’s refusal to reveal it is a kind of standoff of greed (which mirrors in a way the much larger standoff based on greed near the end of the book). It is important to recognize that Bilbo is not portrayed as totally good, here: he and Gollum share similarities.
Gollum slips away, and Bilbo is afraid that he will attack and eat him. He slips on the ring without thinking, and then runs as he hears Gollum coming. He trips and falls while trying to run away from Gollum, but to his surprise, Gollum doesn’t attack him, but runs past him. Bilbo hears Gollum talking to himself, saying that “the hobbit” must have Gollum’s ring, and he must not escape with it, or the goblins will capture him, take the ring, and use it to kill Gollum. Gollum decides to head for the way out, in the event that Bilbo has gone that way, and ambush Bilbo there. Bilbo follows Gollum, realizing that the ring he wears must make him invisible.
Bilbo’s survival in this section is almost completely accidental, not the product of his own ability or heroism. Even when Bilbo finds his way out, he doesn’t do so because of his excellent sense of direction; he simply follows Gollum. In a way, Tolkien suggests, heroism is something of a myth—skill is necessary, but so is good fortune. Note how the ring—and each’s need and desire for it—has become the center of the conflict between Bilbo and Gollum.
Gollum continues toward the way out, with Bilbo secretly following behind him. Though Gollum can’t see Bilbo, he smells him in the dark. Bilbo is tempted to use his sword to kill Gollum, but he feels pity for him, and thinks to himself that Gollum is lonely, and, after all, hasn’t actually threatened to kill him. So, instead, he jumps over Gollum, and rushes into the goblins’ territory. Gollum tries to catch Bilbo, but is too slow, and stays back, cursing Bilbo’s name.
Bilbo could easily kill Gollum, but he doesn’t. In part, this is because he doesn’t have all the information about Gollum—he doesn’t know that Gollum was going to kill him—but just as much he spares Gollum’s life because he’s kind and sympathizes with the weak and pitiable. Bilbo is hardly perfect, and in fact, he’s a thief who has stolen the ring, but at moments like this, it becomes clear that he’s also a moral character. And this morality and kindness is as much of what establishes Bilbo as a hero in the story as any of his cunning exploits to come.
In the goblins’ lair, the goblins see Bilbo—he has taken off his ring. Bilbo slips it back on just in time, and hides behind a barrel while the goblins try to find him. He sees an open door, and moves toward it, dodging goblins. He squeezes through a crack in the door, but his buttons get stuck. A goblin points out that there’s a shadow near the door, as they near the door, Bilbo pulls himself through the door and out of the mountains, losing his buttons in the process—he has escaped.
The difference between Bilbo’s interaction with the goblins here and in the last chapter is obvious—though Bilbo still doesn’t fight them directly, he now has a powerful weapon for avoiding them and the willingness to take action on his own. Symbolically, Bilbo loses his buttons at the end of this chapter, in which he’s changed so greatly. It’s as if he’s casting aside a final remnant of his old life, and turning to his adventure instead.