Squatter, I have found the character who's referred to as a plum-picker, so one half of the question could be answered. However, I cannot find any references to the person in Tolkien's real life who could compare, despite searching in both of Shippey's books, the Letters, and the Inklings biography. Just thinking about persons Tolkien knew well gave me no insight - the character doesn't sound like either C.S.Lewis or Father Francis. Can you give any clue as to where to find a reference? Perhaps the book in which the story is published has a comment, but alas, I do not have it.
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'Mercy!' cried Gandalf. 'If the giving of information is to be the cure of your inquisitiveness, I shall spend all the rest of my days in answering you. What more do you want to know?' 'The whole history of Middle-earth.. .'
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