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I have a lot of competing associations. None of them seem make it or break it, for me to really like or dislike it. I haven't known any Simons except celebrities and characters, so it's easy to imagine the name as having a character... and harder to imagine a real person. On a real person it might seem about like Francis or Silas - urban, conventional but deliberately un-generic, masculine but not a strong/virile impression.

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If Simon is a character, I think he'd seem: Slightly nerdy or misfit, but not due to being incompetent or unpleasant or too brainy - more because of being sort of inscrutable and quirky. Independent, maybe visionary, articulate but quiet, unsentimental, wiry.
A raccoon comes to mind. ??!

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- mirfak