In this pivotal chapter, Bilbo Baggins finds himself lost in the dark tunnels of the Misty Mountains after separating from the dwarves during an encounter with goblins. As he wanders through the eerie darkness, he grapples with fear and uncertainty, feeling the weight of his predicament. It is during this disorienting journey that he stumbles upon a strange creature named Gollum, who resides in the depths of the mountain. Gollum is a twisted and eerie being, deeply affected by the loss of his precious 'One Ring', which grants him the power of invisibility.

Bilbo and Gollum engage in a game of riddles as a means to determine Bilbo's fate: if Bilbo wins, Gollum will show him the way out, but if he loses, Gollum will eat him. The riddles exchanged between the two showcase Bilbo's quick wit and cleverness, as he manages to answer Gollum's challenging questions. As the game progresses, tension mounts, with Gollum becoming increasingly frustrated as Bilbo continues to succeed.

In a moment of desperation, Bilbo, unsure of what to ask, finally poses a rather unconventional question: 'What have I got in my pocket?' This question is not a riddle in the traditional sense, but it catches Gollum off guard. Gollum attempts to guess several times, but he fails to arrive at the correct answer. Bilbo, realizing he has the One Ring in his pocket, is struck with a mix of fear and curiosity.

Upon winning the riddle contest, Gollum reluctantly agrees to help Bilbo find the exit, but Bilbo quickly realizes that Gollum's intentions may not be entirely altruistic. As Gollum leads him deeper into the tunnels, Bilbo decides he must escape. In an unexpected turn of events, he slips on the ring he found, becoming invisible. This newfound power grants him a critical advantage as he stealthily navigates past Gollum, who is unaware of Bilbo's presence.

The chapter ends with Bilbo successfully evading Gollum and the goblins, ultimately finding his way out of the dark tunnels. This encounter not only highlights Bilbo's ingenuity and bravery but also sets the stage for the larger role the One Ring will play in his life and the adventures to come. His experience in the darkness serves as a transformative moment, revealing his inner strength and resourcefulness, qualities that will be crucial in his journey ahead.