in The Hobbit Gandalf basically pushes him out the door without him really knowing about the whole misson laid out in font of him. all he knows is that gandalf has told the dwarves he is a silent burglar and is perfect for the mission. Bilbo wakes up the next day and is told hes late and is pushed out the door with some haste by Gandalf. since hobbits are humble and don't look for conflict Bilbo simply goes along with it.
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Gandalf worked with the Dwarves in the hope that they would once again take the Lonely mountain, establishing a stronghold to help divert the growing power of Dol Gulder from attacking both Rivendell and Lothlorien.
They got lost when they were trying to get to the Elves' feasts that they kept seeing in the distance.
Bilbo and the dwarves stray from the path because they see a light in the distance. They stray even though they are told many times to keep to the path.
Because he was an honest, well-meaning hobbit and was willing to do what they asked of him.
The dwarves are Bilbo's friends for most of the Hobbit.
He said “Don’t leave the path!”
Bilbo was completely enchanted by the dwarves' music the first time they played (and sang) for him.
Yes, in chapter 9 the dwarves (but not Bilbo) were imprisoned by the Wood-elves in Mirkwood forest.
Eat them.