Whoa, I didn't know the whole "What are you going to do then" scene was in the books. Wow I really need to go read them again.
Anyway, I'm not really sure if I can say whether Gandalf had a favorite or not. I think he liked all Hobbits in general. Yes, he might have leaned towards one or the other at different times, but to choose between Bilbo, the Old Took, Frodo, and many others, I just don't think he could have done it.
I think the ones he was closest to were Bilbo and Frodo. Bilbo because of the whole Dragon thing and Frodo probably just because he happened to live with Bilbo and see Gandalf everytime he comes to visit. The other Hobbits of the Shire would probably come next, though. But deciding a favorite? I just don't know if Gandalf even had one.
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