Perhaps Gandalf had some foresight, however, it seems like a bit of a stretch for him to guesse all that would happen to Bilbo. Gandalf always liked hobbits, and there smokes, there wasn't many hobbits who could have caught Gandalf's eye by being adventurous. Bilbo was one of very few. Hobbits could be very queit and would be an asset if you were to sneak up on a dragon.
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"Wake up! Wake up! Wake up, sleepies, we must go, yes, we must go at once."
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