Why Did Bilbo Play A Riddle Game With Gollum. After Bilbo answers his first riddle with ease Gollum challenges the hobbit to a game. But if Bilbo defeated him then he would do as Bilbo wished.
Of the line of the Stoors. Since he was lost in. But if Bilbo defeated him then he would do as Bilbo wished.
If one reads the chapter Riddles in the Dark Tolkien makes it clear that Bilbo never actually intended his question What is in my pocket.
Since he was lost in the dark without hope and could neither go on nor back. After Bilbo answers his first riddle with ease Gollum challenges the hobbit to a game. The riddle competition between Bilbo Baggins and Gollum in The Hobbit serves up the trickiest riddle of which is. Bilbo unfairly won by asking Gollum what he had in his pocket.