Quote 1
When Gandalf saw Bilbo, he was delighted. "Baggins!" he exclaimed. "Well I never! Alive after all – I am glad! I began to wonder if even your luck would see you through. A terrible business, and it nearly was disastrous." (18.14)
Up until Gandalf's surprise that Bilbo has survived the Battle of Five Armies, we don't think we've ever seen Gandalf be wrong before. Can you think of other examples? What are the limits on Gandalf's wisdom? How does Gandalf use his knowledge as a tool earlier in The Hobbit?
Quote 2
Gandalf answered angrily: "I brought him, and I don't bring things that are of no use. Either you help me to look for him, or I go and leave you here to get out of the mess as best you can yourselves. If we can only find him again, you will thank me before all is over." (6.9)
Here, Gandalf's insisting that the dwarves go back into the goblin tunnels to help him find Bilbo. Gandalf is incredibly loyal to Bilbo from the start; in fact, his loyalty to Bilbo is what makes Bilbo decide to join the dwarves in the first place. Do we get any indication about what Gandalf sees in Bilbo that convinces him that the dwarves "will thank [him] before all is over"? What is Gandalf's history with the hobbits and with Bilbo's family in particular?