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I think Len, or Leni/Lennie, is a cute nn possibility for Gwendolen. I like both Gwendolen and Gwendolyn, and though I slightly prefer the former, I think the latter is the more 'accepted' form and so would be less likely to be misspelled, maybe.

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I know of a little girl, and her name is either Gwendolyn or Gwyneth (not sure which), and her nn is Winnie (not sure of spelling). I think Winnie on "The Wonder Years" was also a Gwendolyn, and I like it as a nn, along with Gwen or Len/Leni (not a Wendy fan, though). But then there's the Winnie the Pooh association, though not a horrible one, it may bother her as she gets older. LOL. Also, I read a book with a character named Gwendolyn who went by Gwendy. I'm not crazy about it, but it's yet another possibility. :)