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Does Dick get to be one of the one's who knows him well enough to think his strangeness loveable quirks?
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It would be lovely if he did. Anyone who works in the Inn and/or lives in Stock could have gotten to know him very well over the years, or perhaps, but they could have just as easily avoided him, as well.
EDIT: In my post, I had Griffo set up a chess game. I was not sure if chess exists in Middle-earth, but I could not remember any Middle-earth canon games, so I decided to risk it. Anyone can yell at me, and I'll just edit it out or exchange 'chess' with something else.