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For me it makes a lot of sense:
- Bilbo did not know that Gandalf could see him, when he wore the ring. The revelation when Gandalf would have spoken to him while he sought himself invisible would have been a shock. Reading between the lines we can see that Gandalf would have found Bilbo anyway.
- Bilbo not wearing the ring does provide a better chance for him leaving it behind for Frodo. To secure this plan, devised by Gandalf, was the reason for Gandalf looking for Bilbo at that moment.
Respectfully
Findegil
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