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Gandalf was chosen to choose, but did he have to choose specifically Bilbo?
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Yes, if you're still standing by your "Gandalf also lacks Free Will" contention.
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If a mortal becomes fated, that fate extends backwards in time as well as forward. Bilbo had a fate before he ever met Gandalf, because eventually he would meet Gandalf et al.
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I don't get what you're trying to say here.